5 Pieces I’m Excited to Wear This Fall

Can I interest you in a dress over layers? I’ve always liked this silhouette and you could play around with the shirt underneath and different coloured tights. https://www.uniqlo.com/ca/en/products/E478725-000/00?colorDisplayCode=67&sizeDisplayCode=003

Same. I’m in PJs if I’m home ( and admittedly for quick post office or library drop offs ) I abhor “real” pants. Luckily I wear scrubs at work and they are soft and PJ adjacent.

I just picked up the Quince Bella Barrel leg Jean, and it’s so soft and light that they’re PJ adjacent.

I love the Naturalizer Rena boot. It is so comfortable and stylish. Looks amazing under a midi dress. Maybe not Chicago legit but definitely a winter date night win.

I’m with you. There are really just two shoe seasons for me: sandals and clogs. Clogs really don’t work with everything or with all occasions (but I do it anyway!). Also, I’m old (45!) and my feet hurt without support, so it’s basically Birkenstocks all the time. I’ve long since given up on heels, though I still look at images covetously…

As someone who spent the first half of her life in Chicago and now lives even further north, I’m a big fan of nice leather knee high boots as my dressy cold weather footwear. You can wear whatever socks you want with those, because no one will ever see them! I tend to go the sweater dress and leggings route when I’m dressing up in the cold, but if you’re a pants person when you dress up, a cute pair of leather ankle books works just as well. It’s also worth spending on either cute, colorful socks that you won’t mind showing off or nice, dark-colored wool ones that won’t stand out even if they’re visible.

Minnesotan here. I find companies like Sorel are increasingly making cute and funky boots, and I have a few really cute pairs from Ugg that don’t look like Uggs. Frye usually has some good ones too. get a few knee-high boots that can stretch under a wider pant or go with dresses/skirts. Another option is to wear an easy boot and switch your shoes in the car when you get to your destination. I grew up in the 80s and in norrthern Wisconsin we’d run around with no socks and flats in 10 degree weather with snow everywhere, and no hats because we didn’t want to mess up our hair. unreal.

This is 100000% my dilemma too, Sarah. I’m in the PNW and it’s wet and rainy. I’m also very short, and I can make pants or dresses look stylish but casual with sandals or slingback flats. Not at all with cold wet weather shoes.

Chicagoan here. In the winter I default to combat boot styles and chunky Chelsea boots. Also taller flat leather boots. I hate heels even though I’m short. If it’s not too wet/snowy out, I’ll throw on cute gym shoes. Of course I wear winter boots when there’s snow.

LKB, I’m with you. I wear nothing but sandals and clogs. I feel too claustrophobic in a closed shoe after not wearing them since I can’t tell you when, decades ? Used to be flip flops but you’ve all heard my Old Navy flip flop saga after eating them for decades. (Thanks to all who offered replacement suggestions! So kind of you !) So yeah, I wear a rugged sandal or open back clog type things. That’s bad enough. The fact that I started working again and have to wear shoes at all still makes me cry a little.

Omg what an autocorrect fail !! I assure you all, I did not eat my flip flops ! It was supposed to say after * wearing * them for decades. I think I should retire my PJ wearing barefoot self back to bed. Happy Sunday all ! :)

Blundstones! Easy to dress up or down and they have insulated versions too.

Greta–yes to that, and I’ve read some scientific critiques (by clinical kinesiologists) taking a very harsh view of super-cushioned shoes like Hokas making our feet into floppy, lazy hunks of nothing. So interesting, the debate about shoes/feet!

Sending you a hug! And also a recommendation to check out a-line/”babydoll”-cut sweater dresses and soft tights/leggings without restrictive waistbands to keep that airy feeling going while also staying warm and looking put-together. There are loads of dresses like these available secondhand, and for some reason I also feel like Uniqlo would do a good job with stuff like this. Shoes/accessories can dress up a more basic look and even make it more professional, and as a bonus those things hold up when our bodies fluctuate (as they all do!). So grab a knit/sweater dress that floats away from your body in the way you find the most comfy, add a pair of soft, stretchy tights and your chicest boots, bag, and jewelry, and whatever lip color you’re digging now! Finishing with a final hug :)

I was in that same boat this spring – none of my shorts fit anymore, and a lot of my cute summer tops didn’t either. On the one hand I didn’t mind that my body feels more substantial than it used to, but I did feel sad about not getting to wear old favourites again and having to go shopping (not really an exciting errand for me). Sigh.

Now that I’m over 40, I look for the ones with arch support.

Read, “Born to Run” (the audiobook is so good) by C. McDougall and it will explain in the most entertaining way, woven into an epic adventure tale, how flat shoes are very good for the muscles and body longevity once your feet develop strength again after being overly ‘supported’ by cushioning.

I love my Birdie flats. I can no longer where heels, so flats it is. Or sneakers.

Birkenstocks makes a style of flats now. I need that support too; otherwise 10 min in and my feet would be killing me. The only challenge was finding hidden socks to wear with them; my Bombas ones wouldn’t stay on and I had to yank them into place every 15 min or so.

I came to ask the same thing!

Not all flats are created equal. I have loved wearing flats that have a lot of give in the sole – more of a barefoot feel – than anything with a firm sole. My favorites are sam edelman ballet flats (truly better than shoes I’ve bought that were 3x as expensive) and any kind of driving moc situation.

amazon.com/dp/B00B806BFO?ref_=ppx_hzsearch_conn_dt_b_fed_asin_title_1 I have the Freda Salvador ballet flat mary janes which offer all the style with essentially zero foot support, and these heel/arch inserts are a lifesaver. So comfy and removable – I also put them in my Bass loafers to wear to the office. 10/10 recommend!

Ooo Elisabeth, what are some of your favorite patterns?

oh, thats a good one, LRG:-) just finished the Joan Sweater by Kolibri and love it. before that the Japan Sleeves by Joji Locatelli. I’m frkompott on Ravelry.

Yes, me too! I’ve made 15 sweaters and I’m so excited to wear them again! I already ordered all my yarn because most non-US retailers have had issues with the tariffs and last I saw were suspending shipments.

I love Primary’s adult sweatshirts (and tees): https://www.primary.com/collections/grown-ups-sweatshirts?page=1&ref=mobile_nav_link_2_3_1 Just a heads up that my LL Bean sweatshirts have not aged well. Lots of pilling very early on. Good luck!

I just bought a set from Gap for $19 per piece and it is literally perfect, warm, not baggy but cozy. https://www.gap.com/browse/product.do?pid=7655852820002&_gl=1*1g0e0by*_gcl_aw*R0NMLjE3NTcwMDUzMDYuQ2owS0NRanc4ZVRGQmhDWEFSSXNBSWtpdU93ZzdTaU9MVks1U3VINXVmNjBXblhZWVVwd2ZsLTBkcVBiNWZEQi1id2RvZzBUNmY1R3phY2FBa2RzRUFMd193Y0I.*_gcl_dc*R0NMLjE3NTcwMDUzMDYuQ2owS0NRanc4ZVRGQmhDWEFSSXNBSWtpdU93ZzdTaU9MVks1U3VINXVmNjBXblhZWVVwd2ZsLTBkcVBiNWZEQi1id2RvZzBUNmY1R3phY2FBa2RzRUFMd193Y0I.*_gcl_au*NDYxNjE3MzA2LjE3NTI4NjkyNzM.&vid=1#pdp-page-content

Honestly Abercrombie’s essential crew sweatshirt (the men’s version) is incredible. I own four and I’ve worn them in constant rotation for 2-3 years now (daily in the winter since I work from home), and there is NO pilling whatsoever. And since it’s a “men’s” cut it will be a little bit longer. I don’t really like any of the colors they had out last time I checked, but they change them every once in a while so keep an eye out.

I second the Gap sweatshirt! I reach for it often in colder weather and it washes well. Super comfy!

North Face crewnecks are amazing. I’ve had mine for almost a decade and wear it both hiking and as pajamas. So comfy and somehow indestructible, and looks more put-together than it feels. I have a purple heathered one that shows no stains

Left on Friday (the bathing suit company) makes my favourite sweatshirts. :)

Who makes your perfect burgundy suede boots? That’s a succinct description of what I have been seeking.

I’m with you all the way Monica. And SO happy you have fall, as we are in SPRING.. Bring on the Oz summer.

+1 to this! I live in the PNW, and I get anxious the second the days start getting shorter (in June) because it signifies the looming darkness!! And, summer is too short in the PNW. We need to celebrate every last minute of it.

I feel the same way! Fall was the best & I’m still hopeful every year because I’m thinking of the fun (Halloween, pumpkin patch, Thanksgiving, my son’s birthday, my birthday, Christmas!). As a parent it also means sick kids, various, gross, crap going around at school…

Not a parent but I’m with you!! I moved to a northern climate recently and got diagnosed with SAD, so fall always feels like a slow decent into “will I be depressed again?”

I 100% agree! When my kids were little I absolutely dreaded fall and winter. Now that my kids are older (youngest is 11and he can wipe his own nose and wash his hands!), it feels a little better, so hang in there, it will get better! At least the fall clothing is cute and hot soups are my favorite.

Definitely not the only one, Monica. I love fall as a season but not what it represents, and I can relate to everything in your comment as a mom of two young kids. I try to schedule in extra self care in the winter, and romanticize the cold/coziness as much as possible, and get out in the fresh air frequently, and go to a nearby conservatory to get a dose of green…and it is still so hard!

I agree, fall and back to school is such a bummer as a parent! Feels like all routine and none of the excitement.

Such a bummer. 😭 I hate reentering the time of year when our lives are controlled by the DOE.

“Slow descent into the barrel of winter”….. except it’s not slow here in Montana. Sigh. I got the sickest I’ve ever been in my life this July. Probably norovirus. ER visit sick. It’s got me shook. Even though I do home preschool I’ve fearlessly faced autumn and winter germs with courage and an “i never get sick” attitude. Except now that’s not true. Caught the yuck big from a child, it ran through absolutely everyone. Let’s add to that potential ALL THE BIRTHDAYS, our family only gives birth in the autumn lol. Then the holidays. My mom’s apartment building full of elderly and very eccentric people is constantly passing something around, as is my daughter’s law firm and my sil’s pharmacy. Did I mention my husband works with college students?? I am filled with dread. Is hibernation an option??

Hi Monica! I can totally relate. I have 3 kids who are 7,5,3. The winters have been so hard for us. Are your kids old enough to do some sort of activity? Last January I enrolled my oldest in basketball through the YMCA and my middle in a ballet class. This helped tremendously to get us out of the house a couple of times of week and help us socialize! Even the youngest enjoyed just tagging along for a change of scenery.

“the time of year when our lives are controlled by the DOE” is WILD. you know homeschooling is legal right? I would really like to know how the big bad DOE is reaching right into your little home and strangling the fun. Personally I had so much, too much, fun this summer and was so grateful to see the kid out the door and sit down at my computer to meet some deadlines. Balance in all things.

Mado, I know exactly what Julie means. And even with homeschooling / unschooling, yes, there is still a loss of freedom compared to the months when required regulations don’t have to be followed and work shared with school districts. I know what Julie means. And just because she might not dig the intrusions of school, it doesn’t mean a person has to ditch the whole thing. There can be a mourning for summer and reluctance to have days be accountable to outside organizations, no matter which form of schooling one chooses. A person doesn’t have to ditch the whole system as your comment implies, just because they are thinking about the restrictions end of summer brings.

PNW Grateful, I appreciate your graceful response. I know my comment was snarky a knee-jerk reaction – but the way the “DOE” has been villainized in a country that needs more public education, not less, I find rather ridiculous. Sure, the school year comes with more responsibilities and scheduling restrictions. But calling out the Department of Education specifically seems like political nonsense to me. How much does the DOE actually determine the daily impact of any one school on any one family’s life? The original comment seems to me like dog-whistling for a specific political perspective, not just venting about a return to routines and responsibilities.

usually Adidas sambas!

Quince has lots of good options!

I buy lots of cashmere at goodwill, if it has a hole, I visible mend it and make it my own. The older they get the better…. and within most price ranges of 8-12$ a sweater….

Irish brands are great for this! Ireland’s eye, for example. Also Garnet Hill. Also just search by wool type (cashmere, merino) and cut (cardigan, cropped) on Poshmark and you might find some gems!!

Goodwill! I have a slew of wool and cashmere sweaters that only cost a few dollars each.

Reformations recycled cashmere!

I buy all of my sweaters on Ebay. I filter my search to 100% wool, merino and cashmere. I never spend more than $30 and I’ve bought many for about $15. They feel great and have lasted me years with hand washing. I’ve never felt the need to spend hundreds on new clothing – there is so much great stuff already out there. Our planet really cannot handle any more of it. The new stuff tends to have plastic junk blended into it anyway (polyester, nylon, etc) even at high end prices.

I buy my staple wool sweaters at Muji and Uniqlo. If the moths don’t get to them they last years. At Muji I buy in different sizes for different outfits. At Uniqlo I buy quite slim fitting, thin merino crewnecks that are great under blazers or gilets, and with big scarves. When they get a moth hole or a snag in a conspicuous place, I mend the hole and use the sweater for outdoor sports in the winter. They are great for running, hiking or skiing in.

I’ve had great luck on Poshmark, ThredUp, and local thrift stores! I look for sweaters that are 100% cashmere or 100% wool, both some obvious brands (JCrew, etc) but really anything that meets the fabric content I’m looking for. If you don’t want to have to sort through thrift stores, I’d recommend one of those fancy boutique thrift stores – I just found a vintage oscar de la renta 100% wool sweater for like $50! I’ve personally found that many modern sweaters, even fancy ones, pill quickly, have synthetic fiber blends, are thin, etc, so have had much better luck really with anything thrifted from pre-2000ish.

I’ve had the same Uniqlo 100% cashmere unisex sweaters for years and I love them

Hi Laurel! I’m also on the ‘fewer better things’ train (great marketing from Cuyana). I have several sweaters from Everlane that are many years, and many, many wears old. Specifically the alpaca knits. Here is a link to their current version, which I can’t speak to the cut, but the material looks the same. I’ve had some luck sourcing older styles on Poshmark etc. 🤍 https://www.everlane.com/products/womens-alpaca-ribbed-cocoon-crew-almond

I like Boden, and they have frequent sales, and are easy to shop with (free shipping and returns). I’ve found their clothes to be very well made, and not as cookie-cutter monotonous as most of the stuff that’s out there.

Wow, these comments are helpful for my sweater hunt as well! Thanks to all!

I’ve really gotta throw in another vote for secondhand! I can only think of one *new* sweater I’ve bought in my adulthood. I think it’s safe to trust your hand – if it feels nicer than what you see at Shein or Zara or whatnot, it will probably last much longer. If you don’t have the time to dig, a small business on Depop or Etsy would love to provide you with one. The last one I scored was vintage, Scottish cashmere – $6CAD. The only “flaw” was it needed a soak.

I love Alex Mill.

Great tips here. I’ll also add, if you’re shopping new avoid buying anything with synthetics – it’s shocking how many words brands use to describe synthetic materials. Those tend to stretch, pill, and stink! Wool irritates my skin but I found some 100% cotton sweaters from J. Crew and Gap over the past few years that have held up well so far.

another vote for buying pre-loved cotton or cashmere. the brands we used to trust for quality are letting us down but their sweaters from decades ago are still going strong. there was a good article about this in the atlantic a couple of years ago: https://www.theatlantic.com/technology/archive/2023/10/sweater-clothing-quality-natural-fibers-fast-fashion/675600/

I also love the Ebay vintage wool sweater search! Since I can’t deal with the itch, I have several tissue turtlenecks from JCrew that I wear under them. Sadly the quality went way down the past couple years.

Woolovers! I have a lot of wool sweaters from them, but also some cotton shirts and sweaters. When they have deals, they are pretty good.

I can’t wear wool so it’s 100% cotton or 100% linen for me! I wash in cold inside-out and lay flat to dry, and I wear them for years.

I love bright colors, too. I’m still not where I would like to be as far as wearing wild combinations in suburbia, but I would recommend starting with some really bright accessories. A bright colored crossbody bag makes a big statement, even on an all black outfit. Quirky red eyeglass frames helped push me into being bolder!

AMK, I’m a big believer that you can get away with anything (fashion- but often other-wise) as long as you look (and act) like you did it on purpose. The other thing I like the remind myself is that I’m often looking to other people around me to see if I’m doing it “right,” but for all I know some other random person is scanning the crowd and looking at me and assuming *I’m* the one who knows what they’re doing haha. Why shouldn’t I be the one setting the standard?

I love this, AMK! I live in a reasonably large & artsy community now, but I spent my first 18 years – and a visit every couple months since – in a very unfashionable little town. Perhaps it was teenage defiance that was never outgrown, but the ONLY way I’ve ever been fearless is with clothing. For transparency, some people have suggested that it’s easier for me because I have a small body, but I refuse to believe that style only exists for certain individuals. I honestly can’t remember hearing negative feedback or stares. Ever. Compliments are common, though. I’m almost 40, and I think having spent so long dressing my body in a unique way has helped me deal with some of the less welcome aspects of aging. I’ve never, ever regretted dressing according to my mood that day, and once you get accustomed to it, I think you’ll feel the same.

The best advice I can give about fashion in a lackluster hometown environment is to, “Be the change you wish to see…”. Applied to fashion, it really helps to just become the person you wish you were seeing all around you but are not. You will be the inspiration for others around you. Make it happen! Be the change.

Aw thank you, friends! I’ve saved your advice on notes in my phone ❤️🫶🏽

Yay!

Heck yes! The Eagles are one group match away from making it to the quarter finals. I feel like the rugby World Cup this year is a 6 week Here Comes Fall celebration. Loving spending my weekend mornings watching all month long. And Joanna, I, too, am a delicate flower but I still survived four years of college rugby (and met my wife and best friends on the team). It can be done!

I was here scrolling through the comments hoping that someone would have mentioned this!!! I played rugby in uni and it was so much fun!!! I’m here in England, and the Eagles were training at the University where I work before the tournament kicked off … I was looking everywhere to see if I could spot Ilona Mahet, who is my total favourite … then one day I saw her walking back from training and totally failed to sau anything sensible and/or get a selfie … it was a few weeks ago now and I am still so disappointed with myself!!!!

I’m with you, Megs!!!! I have a fever and the only prescription is MORE SUMMER!!

I feel the same about summer. It’s never long enough and being from Chicago I wait sooo long for the long, carefree, sun filled days. As the days get shorter I don’t look forward to the dark , dreary and cold days ahead. They seem to go on forever.. Trying to soak up every last minute while everyone is already decorating for fall and Halloween. No thank you!

Summer forever! Clinging onto the last pieces…. though I know I should be welcoming the transition to fall…..

Yes, Megs! I see you. As a fellow PNW dweller, I am trying to soak in every last bit of summer. The outdoor public pool near me closes tomorrow and I’m so sad. I usually swim for an hour and leave, but today I stayed in the water for three hours because it was so beautiful and I just don’t want to let go of that summer magic.

Megs I’m in Seattle and each year I mourn, and I mean truly mourn, summer. I will miss going to the beach and texting my friends ‘meet me whenever, if you want!’, sunshine all day, outdoor music/art/food/dancing, neighborhood block parties, drive in movies, etc etc etc. I will probably cry come fall, but I am trying to embrace it!

Hi Megs! I’m with you!! Fall is my absolute least favorite season. It’s the beginning of chaos, the looming slog of the holidays, the death of all the very best flowers and produce. Summer is so free and joyful and loose – and it flies by too fast!

Megs I’m with you on this! I’m such a summer girl…can’t get enough of the warmth and ease of June-August in Minneapolis. I yearn for summer the rest of the year. Transitioning to fall is hard despite the cozy sweaters. Sandals and good tomatoes and forever!!

I don’t long for the end of summer, but the heat and the wild fire smoke and the worst of my allergies in August and September do wear me out. I love the beginning of summer, before the heat and the smoke, and this time is the farthest from them. I love many things about autumn, but it’s so fleeting here in Montana. Some years winter shows up in September. I also feel a little over whelmed with the holidays and our family’s “birthday season”. Although we are doing secret Santa this year for the first time (yay!!), and it’s my grandson’s 1st bday, so very excited for that. I’m sad to see the gentleness and easy going ness of summer go……

Could not agree more, Megs, but can we get a hallelujah for the PNW summer sweater? Love running my morning errands and eating my porch suppers in one! No one else realizes the luxury!

Fellow PNW-er here to say: same! It’s been a lovely season. My tomatoes are just coming into season, so I’m savoring this sunlight in the sky, on my skin and in my salad bowl.

Utterly agree! My tomatoes and cucumbers have just started cranking and I’m in no hurry to say goodbye to my bare arms and legs for the six months out of the year here that it’s too darn cold.

I am with you Megs! I wish summer could last forever.

Summer seems to have bailed early from Cleveland,oh, but I agree. I love fall. But I LOVE summer, and I wasn’t ready for the wheel to turn!

I feel you, Megs. Fall is glorious here in Ottawa, but it’s like, two weeks long. I’m never ready for winter, but I suppose cute clothes ease the pain somewhat.

I felt this way when I lived in the PNW. The summers there are so nice and always felt way too short. Since living on the East Coast I am more into fall.

I feel the same way Megs ! This is my 3rd summer in the PNW. And I absolutely love the weather ! The summers here are unbelievable. I have my windows open from April til October. I do NOT miss PA weather at all ! I do miss the cicadas and fireflies though. <3.

I see you Megs! Fall stresses me the heck out – summer for life!

I see you Megs, I see you! This has been an especially beautiful Seattle summer. August always brings big time Sunday scary vibes for me but when I start spiraling, I always try and remember the rainy wait is so worth it xoxoxo

i’m with you. they can wait. summer forever <3

I feel the same!! Why are people rushing out of summer when it’s still the season?? It’s been in the 70s and 80s where I am and if it were spring and those temps everyone would be in shorts and T shirts…instead it’s all black pants and sweaters. I find people’s fall outfits so drab and depressing and dull. I’d take the bright colors of summer any day and am trying to keep dressing brightly all throughout the year!!! Keeping that summer spirit alive.

Yes, yes, yes, Meg!!! It was just June yesterday! How is it now September?

I’m in the PNW too…I am in “savor” mode. Every last day of summer feels deeply epic and while I happen to fully enjoy the cloudy, cold, 9 mos of ‘hygge’ to come, it makes these last days of summer even sweeter for me, personally. F*%k grief…just savorrrrr!!!! Enjoy!

Pro Tip: They are 35% off if you buy direct on adidas.com – I ordered the orange ones :)

I am pretty sure I learned about Zou Xou on CoJ! My Zou Xou shoes are so beautiful! A splurge, but I feel great supporting this brand. The leather is such high quality and they’re so comfortable! I have Mary Janes in a gorgeous blue color.

What a fantastic birthday gift! You have great friends : )

After extensive Perfect Bag searching (and some purchases), what I actually kept using was a backpack. Water bottles were easily accessible, convenient sections for extra clothing separate from snacks, quick/secure access to keys and wallet in a separate section, and much more secure/ergonomic straps. An an unexpected plus: the backpack was very brightly colored/patterned which made it that much easier for my kids to spot me in public spaces.

My kids aren’t super little but I love my baggu medium nylon crossbody bag. It’s lightweight, washable, and I can fit a bunch of extras in it (bandaid tin, snacks, even a small waterbottle). I have it in olive but this leopard print might be going on my wishlist! https://www.baggu.com/products/medium-nylon-crescent-bag-leopard

i used cuyana’s leather backpack, which looks great after many years of use, and has a handy strap at the top that lets you carry it as a shoulder bag, brilliant.

I know people will trash me for saying this but… I have carried my Neverfull LV bag since my daughter was born 5 years ago. It’s the perfect size. The coated leather never gets dirty. Everything goes in it. My husband calls it my Mary Poppins bag. PS. He bought it for me as a push present that never was since our first daughter, Charlie, was stillborn at 28 weeks. It’s the most durable bag I have ever owned.

Same as Peach on backpack – I went to a delightful light mustard classic Jansport backpack. It became a calling card to my kids.

Baggu cloud tote it’s lightweight, durable, and cute!

Any kind of tote bag situation! The freebie cloth bags from Sézane, my handloomed check bag from Chiapas, a fraying but still chic one from Emersonmade, a big slouchy leather one…

I use a Portland Leather Goods leather backpack (have gotten in nutmeg and black).

I love a giant tote, one that can swallow my child’s backpack, my stuff, library books and some groceries when I inevitably become a pack mule. I keep pouches inside with the necessities so those can be transferred easily. I can also fit a folded up baggu bag for even more capacity. It’s a bit of a matryovshka doll situation but it works SO WELL. Sidenote: My number one piece of advice to new parents is to skip a diaper bag and just enter the land of big tote + pouches inside. It’s so easy to keep necessities in one little tote and that way if you ever want to go on a walk sans diaper bag it’s easy to identify the must-haves and ditch the rest. Also, if you are a pouch person (trademark pending) you get full permission to buy all the Baggu pouches and other tiny little bags of your dreams with the money that would’ve been spent on a diaper bag.

The last few leather bags I’ve bought for myself and a gifts have been on Etsy, from artisans in Ukraine. It feels very meaningful to support Ukrainian makers, the prices are affordable, and quality great. I would buy a big, simple leather totebag for your purpose.

Agree with others, hands free and gentle on your back is going to continue to be important for a long time (my kids are 8 and 12). I switch between a backpack and Uniqlo crossbody bag. The purses are still gathering dust at the top of my closet. I mostly walk / transit / bike places though. If you’re mostly driving I can see the nesting giant tote making a lot of sense.

My fave bag is this woven leather convertible totes bag that can convert into a backpack. It’s so chic and beautiful quality. Lots of compartments too. https://shopvestirsi.com/collections/backpacks/products/woven-bella-tan-2-in-1-convertible-backpack-tote-copy

Baggellini are very practical and I love them. They lean sporty so they are more a day time errands bag. Maybe something like this? https://www.baggallini.com/modern-everywhere-bag/EWH710-BG-B0913-NS.html I love the back pack suggestion for your situation too.

Thank you for all of these great recommendations! : )

Greta I have that exact baggelini bag in your link. I’ve been using it everyday for about 10 years !! I really like it. I don’t really need to carry much but it keeps everything just where I need it and can find it.

Wow, the Naomi Nomi pieces look great. Reminds me of what Tradlands shirts were like ten years ago. Pricy though.

Thanks, Sara. Where has Naomi Naomi been my entire life?!?!?

@L L. I love tradland dresses. They are the absolute best.

Totally! Reminds me of tradlands too. Yes, investments for sure. Very high quality materials, imported plus tariffs, and then cut and sewn in NYC plus the small team – they are very transparent about pricing. I’m a huge fan especially of the merino wool. It’s all I wear all winter!

Mandy, we’re right here!!! Welcome, welcome. Can’t wait to dress you :)

Flat socks!!

Highly reccomend Rothy’s! Have walked miles in them and only took about a day to break in. Also can throw them in the washing machine when they get dirty. https://rothys.com/products/the-square-mary-jane-lollipop-red

I wear these “ultra low” socks with flats, loafers, and closed toe heels: https://a.co/d/gOlnql4 They have a little strip around the heel that keeps them from sliding down!

@Maggie I own those Rothy Maryjane flats and I love them! They are washable amd and super comfy. I was nervous about the strap breaking since it has an elastic bit, but it’s still super sturdy. I waited for a sale to buy them.

I have narrow heels so all of my slip-on shoes have heel liner cushions added. I like the ones that are silicone rather than cloth covered so that they’re more grippy.

I love everything I’ve tried from Camper – with or without socks/hosiery.

Allbirds!

I love the Canadian brand Poppy Barley! Their shoes are soooo comfy, I can walk all day in them. And they’re cute.

Sezane! here’s the link: https://lb.affilae.com/r/?p=5eb1843ec55770653019f763&af=1029&lp=https%3A%2F%2Fwww.sezane.com%2Fus-en%2Fproduct%2Flouisa-jumper%2Flight-chocolate%23size-XXS

Did you mean the one in the photo with the red flats? Because I came to ask the same thing!

I agree, it’s gorgeous. I’m so annoyed with Sezane though for continuing to mix synthetics into their beautiful knits. It makes them pill and smell. I love trousers and silk tops and dresses from Sezane, but I avoid their synthetic knits and shoes. The shoes I’ve bought from them have been either very uncomfortable or easily damaged.

Might mini or midi sleeveless A-line dresses with slim shirts and tights underneath for warmth (if that’s not too constricting for your middle) be a possibility, Gill? They would layer beautifully with cardigans, jackets, and even pullover sweaters as it gets colder, and the silhouette is pretty timeless. This one was my big-ticket investment for the year, and I’m going to be wearing it through the winter with various accessories: https://www.marimekko.com/us_en/maridenim-somasti-unikko-denim-dress-light-grey-094459-091 I also can’t recommend this dress highly enough, if you can find it in your size; it’s crazy-flattering and looks great with layers, and the stitched detailing at the shoulders is lovely. The denim is almost impossible to wrinkle. https://poshmark.com/listing/Banana-Republic-ELLA-ITALIAN-DENIM-MINI-DRESS-6812cc12006e432cb38875e7?

Sweater dresses! Wear it over tights that don’t have a “control” waistband; fleece-lined tights when it’s really cold. You can throw a cardigan or a big scarf over for an extra layer.

Could you still wear the summer jumpsuits with sweaters over them? I know that means bathroom breaks become more time consuming, but otherwise, maybe worth it?

For keeping warm and looking professional in the winter, my secret is boots. With wool socks inside. I have a lot more flexibility about what to wear on the rest of my body when my feet aren’t freezing. Smartwool socks and similar brands are spendy, but having socks that keep your feet warm is a game-changer.

Hi! Someone below mentioned overalls and cardigans. Would that vibe with your workplace? Overalls come in many variations and you can wear all manner of tops underneath. Good luck! Btw, your job must be fascinating!

I love layering a turtleneck under a jumpsuit when its cold! And then knee socks and boots! I also love sweaters with overalls, too. I also love adding a cardigan to those fits but omg going to the bathroom is no fun. Or tights with skirts and dresses, if they arent too much on your stomach.

My stomach area is similarly sensitive. Any chance your sensitivity started after a viral infection, like mine did? Anyways, my clothing strategy for the winter is mostly sweater/sweatshirt dresses with thigh-high tights for warmth (search Nordstrom, there are a few decent options), as well as a wool or tech layer on top under the dress. I have a few pairs of pants that I can tolerate, too. Check out the me + em palazzo pant. It’s a very soft, stretchy modal jersey with a fold-over top. Vuori sells a similar pair, but the me+em fabric is heavy enough that they look like real pants, not athleisure.

Hi Gill, I’m also a university librarian and pants aren’t working for anymore. (My style used to be ironically frumpy, but I’ve crossed over so now it no longer looks so ironic ☹️.) This year I’m going with shift-or A-line dresses from ThredUp. I can wear them with tights/fleece lined leggings and long sleeved t-shirts underneath, plus a blazer or cardigan. (All summer I’ve been wearing nude fishnet tights, which has helped keep me warm enough in the library and non-melty outside).

I can’t stand anything fitted or tight around my waist. These JCrew pants are the best…I think they run big and the elastic waist is loose. They are gorgeous on and can dress up or down. https://www.jcrew.com/p/womens/categories/clothing/pants/wide-leg/CC472?display=sale&fit=Classic&colorProductCode=CC472&isFromSale=true&colorCode=GY6202&color_name=spring-rain

@Gill. Try Elizabeth Suzann. Her clothes are investment pieces but they are amazing. Loose fitting and some how tailored. Adore everything she makes.

Do stretchy waistbands work for you? I wear Athleta pants as work pants all the time, they have a bunch of styles but something like this: https://athleta.gap.com/browse/product.do?pid=198671002&rrec=true&mlink=5050%2C12413545%2Catproduct1_rr_1&clink=12413545&vid=1#pdp-page-content And for a splurge, Eileen Fisher is the queen of pants that look nice but feel like pajamas, with stretchy waists. (

I also have an extreme sensitivity to any tightness around my belly! Like pnwjd said, thigh highs rule! They keep you warm under a thick dress. I’ve also found some wool tights they are loose at the top. Necessary!

Not to hijack…. But, PNWJD, My belly got much worse after my only covid infection. When I had an endoscopy I got diagnosed with “covid belly”, my Somali lining was very inflamed, still, 6 months after the infection. My dr said they are seeing this a lot. I have underlying hypermobile Ehlers-Danlos, MCAS, POTS, and my belly was never ok. But it got so much worse. I’m on a couple meds for it now and I’m doing better. It still flares quite a lot though.

I have developed new sensitivities that have also rendered jeans basically untenable. My best bets have been cotton pants from Pact that can pass for dress slacks and cotton gauze pants. I’m lucky to live and work somewhere where the latter can pass for professional in the right cut/color. Quince makes ponte pants that are relatively affordable and forgiving at the waist. I really liked them for a while but have had to transition pretty much completely to cotton and modal.

I’ve seen people style turtlenecks under jumpsuits and it’s really cute!!!

I can’t stand constricting clothing! No trousers, hoodies, headbands even. I live in dresses, which fortunately works easily as I live in a warm climate. I think the secret is definitely layers and maybe fun accessories to add a professional twist

I had a hysterectomy this spring, and learned that MATERNITY PANTS ARE BRILLIANT for sensitive abdominal areas. I pair maternity leggings with a shirt dress and Blundstones for work, and I’m comfy and unrestricted.

I have not purchased from Toast (due to cost, I’d have to plan ahead for the purchase) but I love so much of what I see there. https://us.toa.st/collections/womens-dresses. And Eileen Fisher often has pants in winter fabrics that aren’t a tight fit, with flat, elastic waistbands.

You need a haramaki! Not tight at all. Centuries of experience dictates that keeping your core warm keeps your entire body warm. HIGHLY recommend: https://www.amazon.com/Kenbi-mirai-Haramaki-Lightweight-Year-round/dp/B0F42NXP6Z

Gill, I recommend the Halara trouser pants. They have an elastic waist band that is comfortable but they do not look sloppy. I like them for travel or days when I am feeling bloated.

Yes! It’s time for the annual reminder to search “vintage white wool fisherman sweater” on eBay. Godspeed folks!

100% this. :).

RAINS mini backpacks!

I recently bought the Lo & Sons OG (used on Poshmark) and I love it! There’s plenty of room for my laptop, files, and notebooks and it has several interior and exterior pockets. I waffled back and forth between getting a nylon bag like the OG or something leather, but I’m glad I went with nylon. It’s lightweight and sturdy.

I recently got the Contigo tote bag with zipper top from WP Standard and am loving it! It is a tote style so it doesn’t come with internal storage but I slipped an organizer I have from another bag inside and find it to be working great for me. I think finding a tote with a zip top is tricky so that’s what swayed me to this one but all of their bags are beautiful – if this style is your thing. :)

Congratulations, Valerie! My work bag is a juniper green Monos backpack, and it’s perfect for transitioning from day-to-day use to lots of travel: It’s very sleek when you pop off the front pouch, the padded inner laptop sleeve is slim but substantial, and there are lots of inner pockets for cords / chargers / shoes(!) / plastic animals / &c. https://monos.com/collections/bags/products/metro-backpack?variant=32562632753226

The Knomo Maddox leather tote is the perfect sleek yet amazingly functional work bag! 17-year lawyer with picky taste here, and I’ve tested MANY bags in my years ;) It has a sleek exterior and interior, lots of great pockets, and even a trolley sleeve if you’re flying with it! And high-quality leather.

I love my Coach tote. I also just ordered the Marc Jacobs Christina tote. Congratulations!

Just gave my daughter the Dagne Dover Signature Tote. Company was founded by female Wharton B-School grads who noticed that men carried one briefcase into meetings but women looked overloaded with a purse, tote, etc. So they set out to make a classic business bag that looks polished. Lots of organization including a drink holder & key. Also offers different colors and other sizes etc. https://www.dagnedover.com/collections/classic-tote#Onyx-Classic

I recently bought Rothy’s discountinued Carryall tote off of poshmark but their classic tote might also work.

Ok hear me out on my hot take: leather diaper bags. Extensive pockets, zippers, elastic compartments. Backpack style to save your shoulders. Laptop compartment. Trolley sleeve so if you travel or attend a conference you can slide it over your rolling suitcase. Water bottle holder. I’ve been using the Mina Baie vegan leather Stevie bag for work for a year and I love it! https://minabaie.com/collections/vegan-bags/products/stevie-backpack

Sleek and practical: I use (and love) the Alemi Viadukt Day laptop bag. I have it in the cognac color and the leather is gorgeous. It is a convertible backpack (also has top handle). It fits my laptop, charger, pencil case, notebook, hand sanitizer, sunglasses, keys, wallet, small makeup bag, umbrella, and a few other sundries. I’m hard on my bags, not gentle with them, and even after using this one for over a year and traveling a bunch with it, it looks terrific: https://alemi-zurich.com/products/viadukt-day-black-soft-grain-leather

I love the cuyana tote bag with the organizer in it. I’ve had mine for about 5 years and it’s held up so beautifully. Feels truly classic.

Check out Nordstrom Rack! Amazing selection. I even saw a beautiful large Cuyana tote for about $80. I ended up getting a beautiful black Coach saddle bag (it has no logos, has hefty hardware and thick durable leather) for about $100. It had endured rain, sweat, drool and life has lifed hard on it. It still looks really nice

Valerie, I highly recommend Cuyana for bags. I can’t remember being happier or more satisfied about a purchase.

I love the classic and chic designs of KAAI bags! I only have a small crossbody bag from the brand, but they have different sized totes specifically designed to carry your laptop and everything else you need for work – neatly organized in the inside compartments. Beautiful *and* practical! https://kaaibags.com/

Congratulations!! Sainte Chappelle. If you can go in late afternoon as the sun is getting low, recommended, but you won’t be disappointed at any time of day. As my art history prof described it 25 years ago: “it’s like standing inside a jeweled box.” She was right.

For a splurgy cocktail night in Paris, hit up the Hemingway Bar at The Ritz!

Bring a book to the Jardin de plantes and sit and read and poeple watch. I like to do it with a coffee in hand which I decidedly American but so delicious in every sense. Also love any of the Roman ruins that have been excavated. The Roman baths, or an old coliseum in the 5th that’s a park now. It’s an older city than I can even imagine.

If you’re planning on doing some of the major museums (Louvre, d’Orsay etc.) I recommend looking into smaller museumes as well, according to your interests. Things like the Musée de la vie romantique, the Musée Carnavalet, the Musée Jacquemart-André, or the Palais de Tokyo. Looking to see what exhibitions are on is also a great way to peel away from the tourist crowd and feel more like you’re actually living in the city. My other piece of advice is to think about what you love that Paris also really excels in–it could be fashion, perfume, art, wine, cheese, music, viennoiserie, art, whatever, and seek some of that out. And let yourself be guided by the city itself and not Instagram or TikTok, there’s so mich to discover beyond Instragram-famous spots!

We did a Secret Food Tour of Montmartre on our honeymoon (specifically the one that included cheese, charcuterie, and chocolate) and it was one of the highlights of our entire backpacking trip across Europe! Just 3+ hours of eating amazing things, drinking wine, and telling all our best stories in a group of instant friends.

As someone forever in search of the perfect denim, I’ve recently been very satisfied with Quince. They have a comfortable amount of stretch but don’t stretch out- my body has changed a lot over the last year or so so I’ve had to part with my previous jeans choices but the Quince selection has taken some of the pain away! Also, I’m still a little embarrassed by the corduroy sounds but not enough to stop wearing them : )

ooh good question! I have a brown and red one from Clare V that I got on sale ages ago. it’s sold out now, but the same size/shape to this one: https://go.shopmy.us/p-24558768

I’m particularly drawn to organized wallets with lots of pockets and bills that are stored unfolded. Kate Spade Staci Continental has been my go-to and I’m on my 3rd one now over many, many years. I love it so much that I ditched my LV and Gucci wallets for it. And despite it’s size, it fits into my very small crossbody. https://www.nordstromrack.com/s/pebbled-leather-continental-wallet/7573308?origin=keywordsearch-personalizedsort&breadcrumb=Home%2FAll%20Results&color=001

I got this little red one from my husband last Christmas with my initials. I love it. https://www.sezane.com/us-en/product/milo-small-wallet/icy-carmine-red#size-TU

Phone case card holders! Having my wallet attached to my phone (which is, in turn, attached to me most of the time) means that when I leave the house, I only have two objects to carry: my phone and my keys. No rummaging around a purse full of gum wrappers for me. Mine is large enough for my ID, two credit cards, and a rotating card for whatever else I need (usually my Costco card or my insurance card). It required some streamlining when I first switched, but it’s been infinitely worth the time and complexity saved.

I haven’t used a wallet in years- I just have a very small credit card holder from Madewell that I love. It can fit in my pocket and be thrown from bag to bag.

I really like my Dagne Dover wallet, and after two years of near-daily use, it still looks brand new: https://www.dagnedover.com/collections/slim-wallet#Onyx

I have the Medium ID Zip wallet from the Coach outlet in gold/walnut/black. Love it – it holds everything that I need it to, the zipper is very smooth and it fits easily in my crossbody bag. https://www.coachoutlet.com/products/medium-id-zip-wallet-in-signature-canvas/CW781.html?frp=CW781+IMXDM

I’m with you MKim – phone wallet for the win! A few credit cards and a $20 bill. I just have pictures of other key items if need be. My only issue is now needing cheaters. I bought some ThinOptics that folded down into a very small carrying case that attached to my keychain. Sadly – the glasses somehow fell out and disappeared. But I have to be ever vigilant that I don’t lose my phone or have it get stolen as that is my LIFE in there!

i don’t use a wallet anymore! just carry my phone for purchases and a tiny leather card holder for my ID/credit card if I want to carry that with me.

Portland Leather Co! Their stuff lasts forEVER and feels great

I’ve been using the one my husband bought in 1993 in high school! We just found it recently, and it still had folded, printed directions to prom inside. It’s perfect, nice and flat with room for a few credit cards and a punch card or two. So maybe a men’s dress wallet?

Also a phone + very small leather card holder when I need it person (I keep my id, credit card, debit card, and costco card in the side slots, and $20 of just-in-case cash in the middle slot). Mine is the perfect tan leather from Poppy Barley, which I would have absolutely recommended, but they very sadly don’t make it anymore. If you’re more adventurous with colour than I am, this Banana Republic one is the same style and currently on sale! https://bananarepublic.gapcanada.ca/browse/product.do?pid=710469013

Yes, I bought one from Quince, and I love it.

MKim – pro tip – you can download the Costco app and have a digital version of your card on there! I also use a phone wallet (#thebest) and it’s amazing not having to remember my Costco card when I go shopping there.

Team phone case! Credit, debit, transit cards all fit plus my library card and a $20 bill just in case.

The Cuyana card holder: https://cuyana.com/products/curved-zip-cardholder?variant=44727984718139&utm_source=google&utm_medium=cpc&utm_campaign=DL+-+Brand+-+Shopping+%28Standard%29&utm_content=brandedshopping&utm_source=google&utm_medium=cpc&gad_source=1&gad_campaignid=6442483884&gbraid=0AAAAADp9_uafJdxGIuD5AOmXbmpIXhKAx&gclid=EAIaIQobChMIieC3pMLCjwMVhTbUAR26WjwyEAQYASABEgJfWvD_BwE

This Kate Spade Wallet if you need several card slots: https://www.katespade.com/products/deco-zip-slim-wallet/KJ650-020.html?ogmap=PLA%7CRTN%7CGOOG%7CSTND%7Cm%7CSITEWIDE%7CMain%7CKS_RTL_Google_PLA_Signal_NA_Generic_National_PMax_NA_BAU_Wallets%7CSitewide_Regular_Core_NA%7C%7C22259989402%7C%7CUS&utm_source=google&utm_medium=cpc&utm_campaign=KS_RTL_Google_PLA_Signal_NA_Generic_National_PMAX_NA_BAU_Wallets&gclsrc=aw.ds&gad_source=1&gad_campaignid=22249526868&gbraid=0AAAAADJUeEWq81oCdV-_hmo20vKwk1qLJ&gclid=EAIaIQobChMInJyW_MLCjwMVJlJ_AB33eSwmEAQYCSABEgLtvvD_BwE

yessssss

“if menopause strikes” = hahahah love it

Ha ha love your lyrics!

“…if menopause strikes…” I love it. This weekend, I told the man I’m dating, “Menopause is coming for me.” He thought that was funny, but that’s how I feel. So I can relate to the idea of it laying it wait to strike.

hahaha freddie and I were playing taboo (the word game) last night and he said “this is what your doctor said to eat less of because of perimenopause” and I was like, “cheese!” the answer was correct, haha.

Jo, time for a new doctor. Lol.

Jenny, for years now I’ve felt a little like the whole damn universe was coming for me. I’ll spare you my series of unfortunate events, but let’s just say losing all the of my beloved dogs in 2 years was proof. Even my therapist will say things like “damn Sasha, just when we think things are getting a little easier for you….” and she’s a professional *deals with people with big problems all day long* person. Anyways, menopause? She can kick rocks. Lol. Making me too warm? Ha!!!! I was too cold anyways, so suck it. My sad little way of coping- fight back with everything I’ve got! And HRT, or whatever they are calling it these days. Will pry from my cold dead hands (that look years younger actually!!! Ha!)

tfw I realize my vibe might be “Dickensian orphan.”

I agree. But I look like a 19th century Dutchman.

I love the barrel/cropped trend but as a 5′ tall person, it’s so hard finding ones that are actually cropped! This might be the year that I finally buy a sewing machine.

Amen! Me neither. Just got back from Europe and saw mostly skinny jeans. I’m so tired of ankle length. I live in a cold climate and I want my ankles covered and/or a good length for short boots.

oh my god ,ahaha M M I’ve been describing my style as “kind-of like a little boy” for years, little did I know that Dickensian orphan was waiting in the wings courtesy of EPFB

I thought this barrel trend was happening 3 or 4 years ago! But I am so surprised to see these all over the place this year, like they are a brand new thing! Don’t know what to make of the time gap but I am slowly integrating slimmer straight legs into my wide leg choices for winter. I already got rid of any barrel legs I had and I’m not getting more, lol.

I know EXACTLY what you mean when you say “2000s Abercrombie vibes” — all those cable knit sweaters!!!

I don’t understand how anyone over 25 is wearing miniskirts. How do you sit down? Doesn’t your bum show when you bend over?

good q! for me, the mini skirts I wear go down to almost the knee. here’s a photo if it helps! https://cupofjo.com/2025/08/19/five-pick-me-ups-4/

Have you seen the Hollister 2000s collection?! I wanted everything – plus the skirts come with built-in shorts now.

@Heather, wearing capri-length yoga pants is my solution! I feel more comfortable and I can still wear a mini-skirt.

I realized recently and amusedly that I only wear mini skirts during the colder months, because I always wear them with tights and boots and some sort of flattering long-sleeved top/sweater. Mine are quite short and I don’t think I could wear them tights-less, but tights, even semi-sheer ones, keep everything feeling functional and non-exposey.

Yesss, Hilary! As a super short grownup, I’ll forever love a mini – it will always look proportionate on me without any need for alterations. And for you regular-and-tall folks, I admire how leggy and model-y it makes y’all look.

My daughter just started 9th grade and 90% of the girls in our suburban high school wore one of those tiny denim skirts on the first day! With the same 3 or 4 sneaker styles (neutral Adidas Canvas, white OnClouds, or Nikes). I am really floored by the way single trends take over right now – I don’t think Seventeen magazine had quite the same effect on fashion in the 90s that Tik Tok does now!

You have amazing taste.

these are so fun, Lauren O.!

Please consider this my official request for a week of outfits from Lauren O.

Dude will you do all my shopping for me please?

sale oubliette! amazing.

Second the week of outfits request!

Third that week of outfits request – love all of these. I am inspired!

ooh thank you! love the shape.

Check Sierra online! Can be hit or miss but I’ve gotten a couple of pairs there on major markdown.

I’m not sure how your coworker meant that remark, but I would take it as the highest compliment. Steve is an outstanding human being. I’ve gotten “very Mister Rogers” a few times for wearing my cardigans and habit of immediately putting “house shoes” on, and “very Ms Rachel” for my hair bands, overalls and way of speaking. I’m a preschool teacher and I take all of this as incredibly complementary, as these are my actual heroes.

omg Steve from blues clues, I am laughing out loud. speaking of, I loved this dating story Steve told on the Moth podcast ages ago: https://themoth.org/radio-hour/blues-clues-stowaways-and-marital-surprises

I couldn’t quite tell my coworker’s intent! I LOVE Mister Rogers. I dressed up as him for Halloween when my son was 2 (he was in a tiger costume, my Daniel Tiger!!!). I used a red cardigan, tie, and plain sneakers. Ms. Rachel is a saint for her activism.

Sasha in Montana, Mister Rogers was my pandemic fashion muse hahaha. Special cardigans to wear at home, loose pants, sneakers. Leave the fashion uncomplicated to focus on the big stuff.

Swoon… Nili Lotan… this is the dream!

AMAZING. I am obsessed with those.

me too! but my bank account isn’t so I’ve been doing some aggressive poshmark/sales lurking. it’s actually been pretty good! you have to wait it out and do some back and forth but I’ve consistently been able to find them for under 200 with some haggling.