July 14, 2026

The Vacation Dress I Can’t Stop Thinking About

Alison Piepmeyer vacation dress

Do you ever pack a pretty dress for a trip? Sometimes I’ll just throw a bunch of everyday clothes into a suitcase. But when Alison returned from a family trip and showed me this photo, I remembered the joy of a Vacation Dress.

“I packed this dress and reached for it all week,” Alison told me. “The breathable linen was comfortable for everything from long sightseeing walks to dinners in the town square. The fabric didn’t wrinkle in my suitcase, and the brown shade hid the inevitable kid stains.” (Here are similar red shoes, too.)

Inspired, I scouted a few more, perfect for restaurant dinners or just swanning around…

The Vacation Dress I Can’t Stop Thinking About

1. Elegant brown. Fun fact: Did you know Magnetic Fields singer Stephin Merritt wears only brown? I once interviewed him for a New York Magazine story, and he said the same thing about stains: “Brown shows absolutely nothing. You’d have to spill some fuchsia paint.” I love Alison’s linen dress and this polka-dot midi — both are on sale.

The Vacation Dress I Can’t Stop Thinking About

2. Crisp white. This dress is a splurge, but how beautiful is the eyelet hem? Honestly, it would work well for a casual wedding. Two less spendy options: linen and lace-trimmed.

The Vacation Dress I Can’t Stop Thinking About

3. Burst of red. Red looks so striking in the summer, especially against blue water and green trees. This easy silhouette feels like something Marianne would wear in Normal People, don’t you think? I’m also into this midi and cheesecloth.

The Vacation Dress I Can’t Stop Thinking About

4. Chic leopard. My friend Frosso reports that everyone is wearing leopard print right now in Paris. Noted! I’d go for this cotton midi or cool shirtdress.

The Vacation Dress I Can’t Stop Thinking About

5. Pretty floral. Finally, how sweet is this mini? It feels like a wild garden, and I want to wear it with flip flops all summer. Embroidered flowers are lovely, too. xoxo

Thoughts? Which dress would you choose? (This one is also so lovely.)

P.S. The random thing I get the most compliments on, and a verrrry low-key summer checklist.

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Comments

96 comments
Anja

When I saw the photo of Alison with the brown dress I thought “wait, I have a similar one”. Turns out it’s the same dress I bought earlier this year. Now I feel fancy. Anyone can relate? :-D

Alison Piepmeyer

Anja! I love this. Twins! xx

MSM

Alison, you have convinced my to buy this dress. So chic! But I can’t be bothered to iron…does this wash up well?

Alison Piepmeyer

Oh god, I hate ironing. I’ve washed this a few times and love how it wears afterwards. It comes out of the dryer slightly wrinkled, but they fall out quickly! I’ve never thought twice about it! xx

Ashley

Perhaps after you’d posted about her previously, I recently came across Frosso’s Substack, and have been enjoying it tremendously. She recently wrote an article about the French vacationing in Greece, which I absolutely devoured. Highly recommend her Substack to other COJ readers – no surprise she is a friend of yours, Jo! <3

Annie

Wah! I just ordered that white Tuckernuck dress to wear at my wedding. Sadly, the top is kinda weird fit and unlined. The search continues for a dress not made of plastic.

Madz

I tried on that little floral dress at Anthropologie and can confirm it would be a perfect vacation wear! Super breezy and lightweight. I didn’t see myself reaching for the color, but I keep checking the website to see if they’ve restocked it in black.

Annie

The eyelet. Adorable. And I love brown but it doesn’t suit me now I have silver hair. A friend who can wear it came round wearing a simple chocolate brown satin dress the other night and I was envious. She looked exactly right. She always does.

Abesha1

The white Tuckernuck dress is lovely! But, even though I see that it’s in their own description of the dress, it’s not eyelet. Embroidered, yes, possibly in the style of Battenburg lace? But eyelet is a specific type of embroidery, and that’s not it. It disappoints me when even the people selling something don’t bother to get it right, or know/care enough to try (them, not you.) Maybe especially because it is a higher price point.

Cate

I recently got caught in one of the London heat waves and ended up living in a dress from J. McLaughlin that is 98 percent cotton and 2 percent spandex. I wore it everyday, washed it out in the hotel sink and hung it to dry in the hotel sink each night. I was amazed at how good it looked-I think the spandex helped it keep its shape without getting the droops! J. Mauling is pricey, but I have found their products great for travel-especially work trVel because they are usually washable, manage to look professional and I have been able to add coordinating items season after season. ( Not sure if this will continue as they have just changed designer/ creative director). Their stuff is pretty tailored in style, but if like me you forsook creativity for law school. -they work!

Mandy

I feel like I may be in the minority with this comment but I rarely ever reach for my quince pieces. There is nothing particularly wrong with them but they are never go-tos for me.

Andrea

Oh the red cotton cheesecloth! What a flattering twist, and the little details on collar and sleeve stole my heart!

by and by

I loved that one too. So sexy!

Zoe

I would love recommendations for summer clothes that are good for breastfeeding!! I guess that’s a bit niche but I feel like this is the place to find stylish clothes that would also work for this (with buttons or stretch that just allow you to… Pop a boob out haha)

Meg

Have you ever shopped at Quince? I believe they have an entire maternity section that is not just for people who are pregnant, but also breast-feeding. Prices are reasonable, quality is great and the generous return policy makes trying on a few sizes and styles very easy.

B B

I bought a dress from Storq a decade ago when I was pregnant with my daughter, it had a button down front for breastfeeding – it’s still part of my summer wardrobe today (even though I haven’t breadtfed for over 8 years)!

Abesha1

Any shirtdress (i.e. button down) is going to be a great choice! Or a spaghetti strap dress, if you’re comfortable pulling down. Aside from that, any shirt that you can pull up from your waist will be easy. Dresses can be the hardest, but separates are your friend. If you pull down from the top and feel exposed, a friend taught me a trick: drape a scarf (or whatever) narrow and diagonally across yourself from shoulder to waist (like a seat belt strap?), before you pull your shirt down. Then you only have a small amount of skin actually showing and baby’s head mostly covers that. I nursed my kids for years and didn’t worry about exposure much, but did also try to be a good ambassador for “this is normal but also I know it’s a little surprising for many people” segment of the full-term nursing cohort. I dress somewhat modestly by choice, so it still surprises me that I was so comfortable nursing in public. The more you nurse, the better you get at doing it comfortably. Last thought- once baby is 4mo old or so, with some head/neck control, nursing in a ring sling (lightweight, linen or cotton) is convenient, and very easy to be discreet by arranging the edge or tail.

Marie

I got a bunch of button-down shirt dresses from Old Navy, and they were perfect. I got two of the black ones because I wore them so much; I just didn’t care — I needed them to be practical and look halfway decent.

Clementine

Seraphine! They went out of business, but you can get plenty of dresses on Poshmark. This was my go to brand during pregnancy and pumping.

Rach

I am all about the vacation dress! Especially in hot weather, there is nothing better than a cotton or linen number and it looks polished in photos, even with nerdy Birkenstocks or sneakers and a baseball cap, my other travel essentials.

roots and wings

You are always so chic, Alison! Can any other readers recommend dresses for bodies with bigger busts? I find it so hard to find flattering dresses for bigger busts. They make me either look very frumpy or huge. Any tips greatly appreciated!

Sarah

The wrap dress is your friend! Those are great for bigger chests.

Stacey

I got the “100% european linen button front dress” from Quince that looks quite similar to Allison’s but with sleeves. I have a pretty large bust (42DD?) and it doesn’t gape. I look amazing because it then nips in under the bust. Seriously, I haven’t found a dress that works so well for my curvy figure in a long time! Not sure if I can post a link here though..

Ollie

Anyone have tips on how not to look frumpy in (longer) dress? I don’t know if it’s the combination of long hair worn down + glasses + my body shape (apple with small bust) but I have basically given up on wearing dresses.

MGH

Ollie- this may not be helpful, but I’ve given up on maxi dresses and just hem them to just below the knee. I love a maxi or mid-calf length on others, but on me it just feels like way too much fabric? If I love a pattern though, I’ll just buy it and hem it myself, or pay a tailor if it’s a fussy fabric.

Anon

I’m a short, glasses-wearing pear with a small bust, and I find that putting my hair up and also big statement earrings fancies an outfit up. For me, either maxi length (down to the ankles) or knee length are better than mid-shin. If the dress hits mid-shin, then a platform or wedge heel keeps me legs from looking stumpy. If you don’t mind trying things on, spend some time trying on different dress silhouettes to see what lights you up so you look for more of that. For example, I find that an empire-ish waist or skater-style fit and flare make me happy, but it took trying on lots of things that I didn’t like on me first. Also, look for dresses in colors and patterns that make you happy. Good luck!

Mollie

Yes- wear your hair up!

Susan

I agree with MGH. I feel like most skirts and dresses are either too short or too long. I would rather buy longer and pay to get hemmed to the perfect length for me.

Jeanne

The Tuckernuck dress is gorgeous but I recommend not wearing white to a wedding unless the bride gives the a-ok.

Mollie

I think she meant for the bride!

Jeanne

Oh right! Haha, duh me!

Hilary

I just got an Abercrombie linen dress from their bra-free line, and it’s AMAZING. Packs well, super comfortable, and perfect for the heat. Makes it look like you really put effort in even though it’s the easiest thing to throw on.

Aubrianne

I recently thrifted a cute, red linen dress, very 90s in silhouette. I sewed up the button placket so it wouldn’t gap, cut off the belt loops, and now it’s in heavy summer rotation. I’ve received a compliment every time I’ve written it, even just walking the dog. I guess the moral of the story is remember to skip secondhand first!

Lala

Last time Alison did a week of outfits, it was terrible for my bank account, but I LOVE her style. Could we get another???

Alison Piepmeyer

You just made my day! xo

Kass

Where in Greece is this please?

Alison Piepmeyer

We were in Paros. This photo was taken in the town of Lefkes!

Elly

Not really related, but can someone help me find a sunhat? I’d love one that -I can wear to the playground (i.e. sweat or the rogue watergun squirt won’t ruin it) and – that is more stylish than one I’d wear while hiking – is big enough to fit my large head I’m OK with giving up *some* sun protection in the name of style (doesn’t have to be UV lined) but don’t want huge holes.

Kat

Madewell has a couple cute lantern hats right now, and they’re on sale for 50% off!

Sunny

I splurged on a Solbari hat 3 years ago and it’s the only hat I wear for 6 months (to the pool/beach, playground, gardening, ect). https://www.solbari.com/products/ultra-wide-cotton-linen-hat-upf50

Elly

Thanks! re: solbari linen/cotton, is it fairly easy to keep clean? I get hot and I’m concerned sweat will stain.

R.S.

I don’t know if this is “stylish” enough, but my favorite hat is the classic Tilley Airflo hat. Comes in lots of colors, is waterproof, has a hidden pocket for keys & cards, and has an optional chin strap for windy days! They also come sized to fit the circumference of your head, so they should fit a larger noggin. I call mine my Adventure Hat and it has been all over the world with me =)

Andrea

I also have a big head! Scala sun hats are cotton, come in a bunch of colors and are available a lot of places. They are around $30-40 and look good on men and women, if your husband steals it poolside.

Alison Piepmeyer

I love these Lack of Color Hats: https://go.shopmy.us/p-71743544 They’re canvas (so not precious) and they have ties so they don’t fall off easily. They also come in 3 different sizes!

Andrea

Sungrubbies!! I have a ginormous head and they have sizes waaaaay beyond me! I have the “outrigger” and love it!

MGH

Sunday Afternoon hats have worked well for my big head/lots of hair.

Deborah

This is a great company and a great hat; good for the playground and especially good for sitting on patios ;) I have a big head and the large fits me. I’ve had mine for years: https://sundayafternoons.ca/products/havana-hat?_pos=1&_psq=hava&_psid=540957656&_ss=e&_v=1.0&variant=41558263693485

Abesha1

I dislike hats but need protection; I have found deep-brimmed, adjustable visors work well to fit my larger head. Also, when hot I usually wear my hair up in a clip, and can then secure the strap into my clip so it won’t blow away. Then no chin strap is needed. I don’t shop Amazon a lot, but some of theirs are great. (Of course, a visor does not protect your hair or all of your scalp. But my hair is thick and natural so that’s not an issue for me.)

Sunny

To answer the question, yes I find that it washes well! I don’t put it in the dryer though.

Elly

Thanks, y’all are the best!

Caroline

We were just in Spain for the week and it was HOT. I wore a dress almost every day. This one was the best–crisp, unlined cotton, with big, hidden pockets: https://www.gapfactory.com/browse/product.do?pid=1174899001&vid=1&pcid=1041618&cid=1041618&nav=meganav%3AWomen%3ACategories%3ADresses+%26+Jumpsuits#pdp-page-content I had tried a Quince linen one but it had a cotton liner and I was pretty sure I’d die with two layers of fabric.

celeste

Thanks for the affordable rec!

Mona

ASOS has great affordable dresses on sale year round if anyone is on a budget like me.

CLK

I only buy my dresses from ASOS. They always fit perfectly and are so cute, chic— whatever mood I’m going for, they have it.

lisa

I love the idea of wearing dresses, but hate the thigh rub. I live in a very hot and humid area. Can anyone recommend undershorts that are breathable? Everything I’ve found is polyester.

Joanna Goddard

Yes! These: https://thighsociety.sjv.io/Z6JQxX

Amy

Also Megababe Thigh Rescue! I bring a mini on trips.

Toni

I wear cotton old navy bike shorts meant for working out with a little pouch for a phone. I sometimes throw an ice pack in that blessing of a pocket. No judgement zone, right? ;)

R.S.

I too have thigh rub, and I cannot wear dresses or skirts without undershorts! My favorites are Woxer brand – they come in lots of different lengths and rises and are super soft modal!

Andrea

Glide anti-chafe is silicone that you can use there and anywhere that pinches like on your heels. It lasts close to all day. I carry it with me to reapply.

Kacie

I’m not sure which countries they’re sold in, but mine are from Snag. Don’t ride up and very durable.

Barb B in BC

I know you are going to gasp at the word but merino wool bike shorts from http://www.simplymerino.com are the best!! They have 6″ and 8″ lengths, pockets and no pockets. https://www.simplymerino.ca/products/bike-shorts-1

Marisa

Here to second the rec for Megababe Thigh Rescue! I usually just throw on any bike shorts I have though. I think right now my most frequent in rotation are the FLX brand from Kohl’s.

Abesha1

I haven’t had luck with any product that claims to reduce rub. But a skirt-loving friend recommended good exfoliation followed by good moisturizer, and that has been game changing! I had never wanted to exfoliate that delicate skin, but it has worked great so far this summer! I use the Seraphic Skincare mitt Joanna recommended here years ago, and CeraVe cream.

Caroline

Me too!

Susan

What a fun post! I just bought this dress for my trip to Colorado tomorrow to visit family https://www.nordstrom.com/s/8870982?color=44444523LY

CPH

Susan, that dress is so pretty! I bet it will look great in pictures too.

Kaff

That New York Magazine story is one of my favorite of all the time!

Shari

Yes, that was so much fun to read! Thank you, Joanna, for sharing.

Kelsey

OK but the knee socks on Alison’s son are my fave detail. I’m reminded of the Trunchbull (90’s Matilda, anyone—how did this image stick in my brain all this time?)….except on him, stylish!

Alison Piepmeyer

ahahahha! you’re not wrong!

Florencia

Funny timing! I just left from getting a massage and my masseuse was wearing a dress almost identical to Alison’s. I asked her where she got it and commented that it was the perfect vacation dress! (She thought it was Banana Republic, 10ish years ago. A classic is a classic!)

Carolyn

I think about the piece you wrote for NY Mag about people who dress in only one color all of the time. Truly one of my favorite articles and I never realized you wrote it. Thank you!

Martha

I bought a dress recently similiar to the red one, put it has cap sleeves, and is in a lovely shade of moss green….it is light, can be dressed up or down…..and I get so many compliments on it! I can comfortable say “I feel pretty” in it!

Wind the Clock

I consider a dress everyday clothes, and always pack at least one wear-anywhere style, like the one in the photo (especially love that one in the chambray – so perfect!). In my book a good dress can be supremely comfortable, much nicer in warm weather than pants or shorts.

A J

I would love to know where Alison’s red shoes are from!

Caroline

Me too!

Alison Piepmeyer

They are from Small Lot! https://smalllot-co.com/ They are canvas, so they were pretty trashed after our dusty travels BUT I threw them in the washing machine when we got home and now they’re good as new. ;)

dahlia

Just ordered that last mini with overnight shipping for my annual week on the lake next week. Thank you!

dahlia

Followup: I am in fact wearing it right now. I haven’t worn what we called in the 90s a “babydoll dress” since the 90s; I’m 56. This dress was outstanding for hot weather camping, and I love it for bumming around the house. I’m not comfortable wearing it for everyday, as I just don’t ever feel certain it’s actually covering my buttocks; feels too naked! I wouldn’t wear it for an urban holiday without a substantial undergarment like the anti-chafe shorts. But a younger me would have worn it just fine, and me-now loves it for casual things and home, and it’s adorable with wide-leg pants. Cozy and charming.

Evenings free

I have a white cotton gauze maxi dress from Old Navy that looks very Greco-Roman and I love it. The front is really deep cut, I don’t have to wear a bra, and it has pockets. Last time I wore it was to a Midsommer party and a guy said “you have this whole Grecian thing going on and I’m diggin’ it, which was an amazing compliment knowing him.

Lori

Looks like perhaps Alison was vacationing in Greece?

Joanna Goddard

Yes! They visited their Greek family friends :)

Ana

I’ve been wearing two of my newest sewing makes on repeat – one is a white linen slightly A-line dress with a square-ish neck line, pattern by Annie’s Sewing Studio and the other is a black linen maxi with a low back line, higher neck line and side slits, pattern from Paradise Patterns! Both are so so cool on hot summer days for jaunts about town and perfect beach cover ups! Any other sewists in the crowd have any fave summer/vacation dress patterns?

Sarah

I’ve been wearing more skirts (mostly the Caprice skirt from Love Notions in bold rayon challis prints !) this summer and I want to add a linen dress to the mix. I’m thinking of hacking the Ashton tank from Helen’s Closet to be knee-length with a ruffled hem. I saw a dress like that somewhere and I can’t get it out of my head!

mado

I’ve been dipping my toes back into sewing and I’m making a pair of wrap pants for a summer trip but this post has me feeling like I totally missed the mark and should have made a dress instead!

Ana

Hi Sarah! Oh that Caprice skirt looks lovely!! I hadn’t see it before! I love all the different views!! And you won’t regret adding a linen dress to the mix!! An Ashton tank hack sounds perfect!! And with a ruffled hem!! Love the sound of that!!

Ana

Hi Mado, Ohhhh wrap pants sounds awesome for summer and it’s not too late for a dress either!!! :):)

Kari T.

THANK YOU Sarah! The caprice pattern with the 3 tiers is the exact pattern I’ve been dreaming of for literally years now. I had a hot pink skirt just like this when I was teen and have wanting to recreate if for SO long.

Emm

I looove Allison’s Boden dress! So pretty. Heads up that I bought the red Uniqlo dress that you linked, and it has a full inner layer that’s 100% polyester. (No Uniqlo, I don’t want to wear a tight polyester liner dress underneath a breezy linen blend dress?!? Please just made the linen dress thick enough so it doesn’t need a liner! Ughh). I was bummed because I thought it was so cute.

MBJ

I was searching for cotton poplin skirts recently and also finding a bunch lined with polyester! You’re missing the point on poplin if you’ve lined it with polyester, lol. I did ultimately find a good (unlined) version at Madewell.

R C

Can you remove the liner and wear your own slip under it?

Lauren O

Today I wore a shibori-dyed dress with breast pockets big enough to fit an entire box of Triscuits and sent a picture of myself to my text thread with my mom and sister. ME: mom did not like this dress but i bought it at ye brooklyn secondhand place anyway SISTER: Mom is unfun and doesn’t understand why it’s important for you to have so many Swedish fish pockets MOM: Booooooooooooo MOM: I think the word you’re looking for is ‘soul crushing’

Wind the Clock

Shibori is cool, your mom is probably just sick with envy over those pockets.

julie

I own not one – not two – but three pairs of shorts with side pockets so deep and wide that I fondly refer to them as my saddle bags. Nothing feels freer than romping about completely bag-free, thanks to my ridiculous shorts that can fit wallet/phone/granola bar/keys/and water bottle. Silhouette be damned!

Elly

Around the house I almost exclusively wear linen shorts with huge pockets so I can go around the house and just shove things that are out of place in my pockets.

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