Let’s Help This Reader Find a Birthday Dress!

Recently, a Cup of Jo reader emailed us with a question…
“My 40th birthday is this June, and I’m hosting a party in a garden,” wrote Kate. “My anxiety has really ramped up over the past two years, but I’m working through things in therapy and hoping that I’m entering a fresh chapter. I want to feel chic but fun, and I’m ready to paaaaaartyyyyyyy. What’s a special occasion dress that’s not frilly or frumpy? I’m okay with a splurge.”
I’M Ready To Party!!!! – Bridesmaids GIFfrom Bridesmaids GIFs
Happy (almost) birthday, Kate! What a fun question, and I’m excited that you’re throwing yourself a party. (I threw my own birthday party last year, and it was one of my all-time favorite nights.) Here are a few dresses that might work beautifully…

1. Pink is gorgeous for spring, so how about a striped dress or this cotton number? I also love this linen one, and what beautiful magenta silk.

2. Red always makes a statement. I loooove this cheesecloth dress, which would feel cool and breezy all night (and would be great for summer trips, too). This linen midi, at a lower price point, is also cute. Or go for great details: these straps are so romantic, these buttons go alllll the way down, and how gorgeous is this back?

3. Channel a flower yourself with this highly rated maxi (with pockets!) or a very pretty mini. And lovely is this blue number? Also, my friend has this Sea floral skirt, which was a big splurge but gets a million compliments every time she leaves the house. “Even my 20-year-old boy neighbor was like, ‘I really like your skirt,’” she laughed.

4. Finally, polka dots are a big trend right now, although I’ve always loved them. This sundress is lovely, this midi has a cool square neck, and how playful are these colors? And this dress isn’t technically polka dot but it’s a VIBE.
Thoughts? Which would you choose? Or would you recommend a different look? I also like these chic shoes. xoxo
P.S. More reader questions, and 12 readers share their favorite birthday celebrations.
Tags: reader shopping
Comments
97 commentsWe need a follow up on these posts to see what the original reader ended up wearing! Kate, let us know! And Happy Birthday, welcome to a beautiful decade.
I always love clocking these posts but am struck by the lack of sustainability focus. Would be so great to see some garments included that are both accessible from a price point and are emblematic of preferred materials and supplier practices. I’ve worked in the field for 15 yeas and am always happy to share my best sources! Thanks
Happy almost Bday! That red one is amazing! Let’s be women who wear stunning red dresses.
I just got one of those color analyses done today—I caved lol but it was actually VERY educational and worth it! But one thing I learned is that true red (think Santa) actually goes beautifully with everyone’s skin tone, no matter what “season” you are. Do with this what you’d like! Happy birthday, friend!
This was so helpful as I was debating a red dress – refused to spring for a color analysis- but always imagined I couldn’t pull it off! Thank you!
I love dresses. I often feel more comfortable in a dress or skirt vs pants! Here is Raleigh there is a wonderful shop that I love, The Flourish Market. They are size inclusive online + in store!! It’s woman own + all brands of clothes, homegoods, etc are ethical made. They have made huge impacts in communities around the globe over during their decade of business. They have so many gorgeous things at fair price points. https://www.theflourishmarket.com/collections/dresses-1 https://www.theflourishmarket.com/collections/bottoms
I am an online customer and would love to shop there in person someday!! It’s fun reading Emily’s updates!! P
Very bummed that not a single plus size model/dress is included in these links. I don’t know if that’s a reflection on CoJ or on the industry right now, but either way, it saddens me. I’m still fulllllly in the body acceptance movement of a few years back that apparently is fading away, so I read.
thank you so much for your note, heather. I always appreciate the feedback. we could have done better with this post. we always strive to feature a range of sizes (the j.crew pink dress and floral mini come in sizes up to 4X; the Anthropologie floral Somerset dress comes in sizes to 3X; and the Alexa Chung x Madewell dress runs from 00-28), but we could have included more, for sure, as well as a few picks from beloved inclusive brands Universal Standard, Elloqui, etc. And of course the models could have been more diverse in this way. my apologies, and thank you so much for taking the time to write your comment. I’m adding a few more links in to the post right now to reflect this. thank you, heather. xoxo Joanna
Thanks Joanna. You and your team are wonderful.
Heather, this local shop in Raleigh has beautiful options for plus size. Take a look around.. https://www.theflourishmarket.com/collections/dresses-1
Love love these beautiful dresses from a small Canadian designer – https://peachroseclothing.com/
Just layered two coupons together to buy myself a white boden dress: https://us.boden.com/products/women-arabella-cotton-maxi-dress-white-broderie-d1530wht Now I just have to figure out how to eat pizza and drink coffee (not at the same time) without being a complete klutz!
Oopsies, I didn’t need a dress but now have a dress on its way to me. I just felt so inspired!
This took me down many retail rabbit holes and I’m now madly in love with this, in both colors, although I have nowhere to wear it, it won’t look like that on me, and it’s about 500% over my usual budget: https://www.shopdoen.com/products/riviere-dress-black
I was going to suggest this dress: https://nordstrom.sjv.io/4aWQAn I thought it looked a bit like Halle Berry’s early 2000s Oscars dress, but fresher? And then I looked at the price–yowza! And I didn’t notice in the small pictures that the flowers have some sequins which might be a bit much for a garden party. But what a stunner.
Hey, she said she wanted to splurge!! Lol. $8k. Can you even imagine???
Oh yes to the flowers dress!
I know this has been mentioned a few times but yes to Nuuly! I started while pregnant because I didn’t want to buy new maternity clothes for my 3rd pregnancy and it kept my closet fresh as my belly grew. And then postpartum it was wonderful when I wanted to wear “real” clothes but wasn’t my normal size either. Now I use it because I find that it curbs my spending – if I find myself eyeing something, I go to the Nuuly site to try and find something similar to rent the following month. And the good news is that if you like it, you can usually purchase it for much less. So many Somerset (and similar Katerina style dresses) in beautiful fabrics! Lots of stunning choices for this reader!
My Nuuly just came today and I love every single thing (which is rare but not unheard of!) I’ve been doing it for about 4 years now, and it’s very easy to pause and restart when needed. My #1 hack is to sort by “newest” always. You get to try very on-trend things currently in the Anthro stores for a month. All 6 things I ordered this month came new with tags. Some things can show wear quickly, but sorting by newest is a game changer. I agree- so many good garden dresses on there!
Yes to Nuuly! @lauren A I have never thought to sort by newest but that is an AMAZING idea. Saving this tip for next time. Thank you!!!!
+1 for Nuuly!
Omigoodness… the red dresses! THE RED DRESSES! ALL of them! I neither need nor can really afford three fabulous new dresses, but I’m still tempted to buy them all and turn them into my signature summer look! ❤️☀️❤️
I would suggest the brand DoubleJ. Very unique style and yet, timeless. I really like this one : https://go.shopmy.us/p-56802163 Happy birthday ! xx
Echoing requests for a follow up! I love reader questions and the follow ups feel like catching up with a neighbor
great idea!!
Yes! What dress did she pick ??
Happy birthday to Kate! 40 was my fave decade to date! I am turning 50 this summer, while in the middle of an amicable divorce, and decided to throw myself a garden party to celebrate too; loosely themed “A Midlife Summer Nights Dream.” I don’t have any dresses to recommend, but am loving all these options and checking them all out too!
Amazing theme!
OMG, we must know what dress this reader chooses. May she purchase well, feel divine and have a gloroious evening.
Yes!! Sending beautiful, vivacious party vibes. Would love a follow up feature on what she went with. My vote is #3 flowers – feels special and milestone-y!!
I definitely recommend Nuuly or Rent the Runway for something like this! You can sign up for the monthly subscription (just cancel after the month you use it) and pick out 5-6 items to try. It feels a lot less high-stakes that way! Make sure you look at the reviews to see pictures of the dresses on real people; that helps!
A desert island dress perfect for a romantic garden party. Reminds me of my favorite flower, the café au lait dahlia. https://go.shopmy.us/p-56801496
Boden dresses are my absolute favorite- flattering, comfy and so pretty. Happy birthday!
This wildflower dress! https://www.universalstandard.com/products/louvre-bow-back-linen-dress-wild-flower-bouquet-print-on-stripes
Oooh, I’ll be stalking these comments, looking at all the links!! One thing I noticed is that every dress mentioned in this post has a distinct waist. In my late 40s/early 50s, all I want to wear is A-lines. Between endometriosis and peri-menopause, my middle section is tender/sore at unpredictable times. I have a couple of forgiving A-lines (Eileen Fisher ebay) that I absolutely live in.
https://www.nililotan.com/collections/dresses I wore a Nili Lotan spagetti strap slip dress on a trip last weekend, out to brunch, and it was the most comfortable thing I brought. I also felt like a million bucks. (It was a gift from a friend). It’s almost an exact copy of a 90s slip dress I wore on my honeymoon in 1995, and my husband recognized it! “I loved that dress on you” ❤️
Ahh, isn’t he sweet – and your friend, too, for that matter! Slip dresses really are so sexy!
I hope we will get to find out what dress Kate actually wears! Fun times! I had a four month old baby at my 40th birthday party and it did not even occur to me to dress up. For my 50th I was in Peru with friends and wore something packable and versatile. Maybe for my 60th I’ll pick out a killer dress.
I’ve recently discovered kaftan dresses from World Market and I can’t stop buying them! They’re all over Poshmark and the sizing is perfect for me. I’m 5’10” and a size 16/18 and the L/XL fits like a dream.
Yes to the Somerset Maxi dress! I bought one 4 years ago and it was worth every penny. I wear it all the time and get a ton of complements.
I wore that exact floral one for easter thanks to Nuuly! Definitely recommend renting the Somerset if you go that direction. Whenever I don’t know what to wear I just see which Somerset is available on Nuuly
If you’re looking to stay more on a budget, Poshmark is a great place to look! I got a magenta lace Boden dress new with tags for 1/3 the original price. One of my most favorite dresses ever! There are TONS of the Anthropologie Somerset dress as well.
These are all such gorgeous recommendations. My 40th Birthday is ALSO this June but I will be 30 weeks pregnant and am really discouraged by all of the standard maternity brands available. If anyone has any pregnancy-friendly dress ideas I would be so very grateful!
Rent a dress!! Nuuly is great for maternity AND for one off occasions.
Other commenters are recommending the Anthropologie Somerset maxi and I just want to chime in here and say I wore it through the end of my second pregnancy. The elastic waist makes it a good non-maternity maternity option!
Elizabeth Suzann
I’m in a pregnant/postpartum/breastfeeding stage of my life and I’ve been really loving Neuflora. The waists are mostly slightly higher than normal, the stretchy necklines pull down to nurse, and the colors and prints are so lovely! I think I’ll be wearing them for years even after this season of my life, if I don’t t wear them out!
Cara Cara would be my pick if I were splurging! Beautiful dresses and also matching sets. I’ve found some gently used Cara Cara dresses on Poshmark and TRR too. https://caracaranyc.com/collections/dresses
These are gorgeous!
Happy birthday! I recently treated myself to this dress for my birthday — I felt feminine, pretty, and comfortable. https://lisasaysgah.com/products/soho-dress
Any recommendations for a midi-length party dress with an adjustable tie-back waist (or waist sash) and full skirt? or shirt/skirt combo? I have a wedding to attend in a month and am striking out. I am 5’2” and have a short waist, and most dresses are made for longer torsos.
Heritage Clothings has a lot of defined-waist styles in colorful prints. Woman owned. The skirts are mostly elastic waist (wear with a color coordinated silk blouse/top); dresses are not.
Hey Anni – short-waisted 4’11” over here. Vintage will always be my favourite, and I find most of the popular styles from the late 60s and early 70s look perfect on us – I think it’s often called the “Dolly look”. They also had more petite lines then, in general! Modern fare, though? I tend to stick with the Gap’s petite range. It’s often just a TINY bit long on me, so it may be perfect on you. Have a great time!
We have this wonderful shop and if I were 40 and shopping for a splurge of a birthday dress this is where I’d go – https://www.shopcatandkate.com/
La Double J swing dress! 100% silk, made in Italy and timeless. https://go.shopmy.us/p-56741106
I’ve been lucky enough to borrow my sister’s. It’s the perfect dress!
These are unbelievable! Absolutely stunning
Wow! Those are gorgeous
Self Portrait! lovely unique dresses for all occasion, if its good for Kate Niddleton it will be good for her :-) HB girl! https://eu.self-portrait.com/en-de/collections/new-arrivals-dresses
I like the floral Anthropologie dress shared in the post. I’d also recommend something from Boden. They make such comfortable, flattering, and fun dresses. Maybe: Colorful Maxi: https://us.boden.com/products/women-empire-poplin-occasion-dress-aurora-blue-ornamental-charm-d1698grn?_pos=8&_fid=88b1f3989&_ss=c Fun Shift Dress: https://us.boden.com/products/women-flared-sleeve-shift-dress-multi-orchid-canopy-d1729grn?_pos=14&_fid=88b1f3989&_ss=c Stylish Jersey Dress: https://us.boden.com/products/women-imelda-kimono-jersey-dress-olive-tropical-safari-d1492spt Pretty Midi Dress: https://us.boden.com/products/women-nell-kimono-midi-jersey-dress-bright-cherry-ornate-floret-d1495red_pos=58&_fid=e8572f36f&_ss=c Most Comfortable Adorable Garden Party Dress (Boden’s Louisa Dress) https://us.boden.com/products/women-louisa-short-jersey-dress-midnight-teal-floral-frenzy-d1318mn
I splurged on this dress recently and feel especially pretty when I wear it (now on sale!): https://www.nordstrom.com/s/carmel-eyelet-embroidered-tie-belt-cotton-dress/8723506?origin=keywordsearch-personalizedsort&breadcrumb=Home%2FAll%20Results&color=401
Maybe something funky? Dresses are 20% off right now! https://aceandjig.com/collections/dresses
Can I just say THANK YOU to Ace & Jig for having people of all sizes modeling all clothes? I’m so tired of how we’ve gone backwards to stick thin models for everything. I’m not considered fat by most standards, but I have such a hard time imagining most of these recs on my body.
Rachel, I was just thinking the same thing. The models that most brands use (above) do not help whatsoever to picture myself in those dresses.
I’d be heading to Anthropologie. This one maybe? https://www.anthropologie.com/shop/hybrid/the-arlette-square-neck-piped-midi-dress-by-maeve
Boden.
I second this! https://go.shopmy.us/p-56740807
The pink drop waist dress is so pretty! I vote for that one! Would love to see a follow-up post about what the reader picked.
Happy 40th birthday – I have a few summer events to go to and love the Somerset dress from Anthro, I have one in that cut with citrus, and it’s lovely. It fits many different body shapes. Also, Boden USA has always had fabulous dresses, not sure if their quality is that great anymore though. Enjoy the party!
I buy myself a new Emerson Fry dress (last pic, polka dot) every spring. I love them. I didn’t this year, which I need to rectify. I am eying the navy Alex Mill polka dot dress.
Happy 40th Kate! The best is yet to come! If you want to splurge, check out dresses from Zimmermann, Alaïa, Khaite, Cult Gaia and Alexis. Also, make sure you buy early so you have time to tailor and make sure you are looking and feeling your very best!
May your 40s be your best decade yet! This is one of my recommendations. https://www.dillards.com/p/a-loves-a-floral-crew-neck-short-bubble-sleeve-a-line-flounce-mini-dress/521291744 Happy birthday!
Its fun to shop, but anyone else feel exhausted from high price tags and bad quality :(
YES. So much poly, acrylic, rayon too – stylist on a gorgeous model to look dreamy on a website – and sold for way too much money! Whenever I start to fall into the trap of wanting some pricey clothes on a beautiful website, I look it up on a resell site and suddenly the $200 polyester dress doesn’t look so great. Kinda like when the bar lights come on at 2am lol
I’m dreaming of an invitation for me to purchase a cotton poplin skirt from Anthro with oranges. To be worn with a crisp white button up with the sleeves rolled up and tied at the waste. Summer ease but chic. https://www.anthropologie.com/shop/the-jacie-poplin-printed-maxi-skirt-by-maeve?color=080&searchparams=q=oranges%2520skirt&type=STANDARD&size=XS&quantity=1
Yes, me too !!
I invite you to buy that gorgeous slice of summer in skirt form and wear it any and everywhere just as you described (and all kinds of other ways you won’t even think of until you hold it up to what’s in your closet). (Does that invitation count?)
Anything by Farm Rio!! https://farmrio.com/collections/dresses
Yes! I second the Farm Rio rec! I always feel like the main character when I wear anything by the brand.
Yes, speaking of main character energy, how great is this for a garden party: https://go.shopmy.us/p-56802632 You can also rent it! https://www.nuuly.com/rent/products/monstera-sleeveless-midi-dress
#3 first linked dress just takes me to Anthropologie main page…any chance you can narrow it down a little, as that site has a LOT of dresses!
It’s the Somerset maxi dress which is worthy of its rating.
#3 at Anthropologie is The Somerset Maxi Dress, which you can type in their search box.. This was my favorite dress too, with the pretty garden flowers on white, it’s cotton which would be so cool and summery. I purchased this dress in a navy print for my birthday last June and it was perfect, so flattering and comfy. .
I love these artful slip dresses from Market of Stars if a practical magic, witchy sort of garden party is your vibe! https://www.marketofstars.com/collections/boheme-slip-dresses
That first dress pictured reminds me of Rita Moreno’s dress in West Side Story :) similar color and similar drop waste. So cute!
I splurged on a Sezane dress for a spring thing – it is black linen with neutral/tan dots. FIT IS PERFECT and I feel like Julia Roberts in the polo scene from Pretty Woman (IYKYK!). Best part is that it feels very flexible — like, I think I could wear it with cool kicks this summer on vacation in NY/BKLYN? And the change into cute sandals for dinner at night? https://www.sezane.com/us-en/product/fitia-dress/beige-polka-dots-black-background-print#size-2
wow this is so cute! are you able to adjust how many buttons you keep buttoned at the bottom? And agreed, you can dress it up or down!
Omg yes, Maya. I look at their dresses like once a month and always talk myself out of spending the money. Love this dress. Wear it with the shoes, both of them. (I’m mentally fist bumping you.)
Ooh, I love that too, Maya!
I had to check – buttons do not go to hem but are functional. I have three kids and do not feel it is too revealing. So far have worn it to an academic social function, Easter, and a play :)
yes, i think this is the one!!!
OMG I finally splurged for a Sézane, dress, never thought I would. I might wear it for my upcoming 50th birthday and look like an Angine de poitrine fan:)
The third one is utterly enchanting! Happy Birthday!
that pink one reminds me of Amanda Seyfried’s met gala dress!
That is EXACTLY what I thought! Amanda Seyfried’s dress was so pretty. Not a good look on my body type, but what a beautiful dress!
Kelsey, agreed. She always looks so beautiful and that dress was stunning on her… but I also think it was a boring choice for the Met Gala!