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What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

What do you wear on date nights? We posed the question on Instagram and got hundreds of fantastic replies. (They were impossible to narrow down!) Here, 10 Cup of Jo readers share what they wear out on the town…

Above: “When my husband and I get the rare opportunity for an evening date and a break from the drudgery of parenthood that can honestly make you forget you’re the subject of anyone’s romantic gaze, I always end up in something that draws the eye to the neck and clavicle — and an extra spritz of Le Labo perfume. I have a small scar on my chest that took me a long time to accept and I remember worrying that I’d have to resign myself to crewnecks for the rest of my life. But I learned to embrace the imperfection, the same way my partner sees all of my faults but loves me anyway.” — Jennifer, Ballston Lake, NY

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“To be honest, my date look doesn’t vary too much from my everyday look — I like bold, fun pieces. For dates I make sure to wear my good jeans (these are so flattering), add sparkle (a fun bracelet), and do something different with my hair (here I used that Bedhead beach wave curling iron).” — Jessica, Sudbury, MA

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“In Alaska, my dates often include physical activity and extreme weather, where the only appropriate skin to show is my nose. I’ve adopted the adage that ‘there’s no such thing as bad weather, only bad gear.’ I also love supporting companies that prioritize local production and environmental sustainability. My favorite brands are Skida, Salmon Sisters, Patagonia and Dovetail Workwear.” — Jillian, Fairbanks, AK

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“My ideal date is eating Italian food and then walking on the beach. But there have been some dates where we have barely talked, just sat holding each other’s hands and looking at cars and people passing by, and have come home really happy. Each other’s presence is enough.” — Divya, Mumbai, India

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“For date nights, I love to throw on a Karina dress. They are so easy, and as a mom of a one- and four-year-old, I find they’re also great for pregnancy, postpartum and nursing. Plus, they are ethically made right here in my hometown. (I don’t work there, just love the clothes!)” – Kathryn, Kingston, NY

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“My fiancé and I like going out to a movie and dinner. But honestly, since we have crazy schedules, mundane things like going grocery shopping also seem luxurious. Oh gosh, guess I have officially passed my 20s — thank goodness! This dress is H&M from seven years ago! It’s definitely held up well.” — Lakshmi, St. Louis, MO

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“I wore this on a date recently and felt so grown up — I was attempting to channel Meghan Markle’s effortlessly cool style. The date wasn’t great, but I can say I was just as happy coming home to a glass of wine and and episode of Fleabag!” — Anna, Hamburg, Germany

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“I like casual day dates (farmers market, walking the dog around the lake, brunch), so I don’t go for stereotypically sexy outfits. I’m particularly in love with this giant polka-dot vintage sweater that I found at a rummage sale! It makes me feel comfortable in my own skin and like I could go for a jog or climb a fence if need be.” — Teresa, Oakland, CA

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“Makeup is key for me. I rarely spend much effort on my daily face, but when my husband and I get time away from our two small daughters, I like to remind him of the fox he married. If you’re ever needing an instant hit of sexy vibes, eyeliner is certainly the fastest method, in my humble opinion.” — Lauren, Indianapolis, IN

What Do You Wear on a Date? 10 Cup of Jo Readers Share Their Real-Life Looks

“In the process of my husband taking these photos, I realized that while I love putting together outfits, THERE IS A REASON I DON’T OFTEN TAKE PHOTOS OF THEM. (I don’t know what to do with my hands.) Outfit details: Heattech long undies top and bottom, velvet blazer from an outlet, linen wrap skirt from Canadian-designed Cedar & Vine, Costco socks and J. Crew shoes.” — Tiiu, Kingston, Ontario

What do you wear on dates? Please share below…

P.S. What readers wear to work, and what I love to pack for trips.

  1. Deborah says...

    I live in Saudi Arabia, and I have a Date Night Abaya!
    It’s a little fancier than my everyday abaya. It’s got loose sleeves and cream-colored lace.

    I usually wear a nice dress underneath, too.

  2. Tiiu I am in love with your bath tub.

    • Tiiu says...

      Me tooooooo! Thank you! When we renovated our bathroom, a big tub was at the tip-top of the list! :)

  3. Emily says...

    “When my husband and I get time away from our two small daughters, I like to remind him of the fox he married.” What an absolutely delightful comment. Her confidence and beauty made me so happy.

  4. Emma says...

    St. Louis!!!!! Thank you for the Midwest representation!

  5. mina says...

    Loved seeing women from all over the world in this post! BRAVO CoJ!

  6. Lizzie says...

    I LOVE doing a workout (or similar) for a first date (or subsequent I guess). You’re in your gym gear, you don’t look amazing but you work your body, build up a sweat and endorphins and if you like the red, sweaty, messy looking person at the end of it you know you’re onto a good thing!

  7. Ashley L says...

    where is the shirt from in the first picture?! It is perfect!

    • Jennifer Taber VanDerwerken says...

      Hi! It’s from Ann Taylor LOFT—from last summer. ❤️

  8. Shwetha says...

    Joanna, my heart is full reading this post, for several reasons.
    1. You’re one of the only few authentic blogs still around making meaningful connections & building a community.
    2. I love that me as a South Asian, see someone I can relate to. A confident, young Indian woman, Divya.
    3. I love the idea of using the hashtag #cupofjostyle

    Quick question – How do I submit a photo? And how do you pick people for the series “a week in outfits”. I love every single post here.

    Thank you so very much for the community you’ve built.

    Xo

    • Also Lakshmi says...

      Actually two South Asian women (Lakshmi in the red dress)! I also love the representation.

  9. Christina says...

    You all look beautiful!

  10. M says...

    I’d love to see a house tour Anna’s place in Hamburg! I’m super curious about what the windows are like next to the arched support beams in the background :)

  11. Annalisa says...

    Oh my gosh – the Karina dresses. Shut. The. Front. Door. THEY ARE MADE FOR BOOBS. THANK YOU!!!

  12. Dot says...

    OMG Tiiu!!!!

    I recognized you instantly — we lived on the same floor in first year university. You were roommates with Ainsley. I hope you’re doing well — you look great!

    Dorotea :)

    • Tiiu says...

      Hi Dorotea! Gah! Hilarious! I hope you are doing excellent!

  13. Z says...

    I love the reader outfit photos so much! Can we come up with a group hashtag on instagram and we can use it for inspiration for outfits?

    • Joanna Goddard says...

      I love that! Should we do #cupofjostyle?

    • Joanna Goddard says...

      i just added #cupofjostyle to some of our instagram posts. would love to have readers use it, too!!! xoxo

  14. On the date I also add more makeup and wear jewelry. I always wear makeup but keep it very minimal. So on the date I add the eyeliner and blush, and use a different lip color. Oh, I make sure to leave the house with perfume.

  15. Nikki says...

    Went for a huge hiking trip in alaska- fell in love with Salmon sisters.

  16. I love everyone’s outfits! I need to check out Karina dresses.

  17. sya says...

    I want to hear about what GUYS wear on dates!

    • Julia says...

      Yessss. Could Alex write a Cup of Jo for husbands?

  18. Anita says...

    Love all of this and am so happy it is a new series.

    In particular though:
    I’m absolutely obsessed with Anna’s apartment!

    And in love with Lauren’s attitude.

    • Anna Allen says...

      You are TOO sweet. Don’t let this photo of my apartment fool you — right now there are two suitcases strewn about that needed to be dealt with two weeks ago! ; )

  19. Andrea says...

    Teresa’s sweater!!!! I want to be friends with her. Actually I want to be friends with all of them!
    Also really wanting a date now! I felt Jennifer’s sentiments on a date as a “break from the drudgery of parenthood that can honestly make you forget you’re the subject of anyone’s romantic gaze” a little too hard. Oops.

    • Teresa says...

      Thank you so much, Andrea! I want to be your friend too :)

  20. Grace says...

    I want to hear more from Anna in Germany! Her apartment is adorable!

    • Gretch says...

      I second this, I really want to know what the rest of her adorable apartment looks like!

    • Anna in VA says...

      I agree!

    • Anna Allen says...

      You ladies are making me blush so much! <3 Let's be instagram friends!

  21. Kate says...

    I want to know about Jessica’s shoes!

  22. Alicia says...

    I want to steal Teresa’s entire outfit and joy. I NEEDTHATSWEATER😍

    • Teresa says...

      Thank you, Alicia! I GASPED when I walked past that sweater at the rummage sale. It felt like kismet.

  23. Beautiful article. Loved reading it. Look forward to your posts everyday. Really happy to see people from all over the world being featured in your blogs.

  24. Carla says...

    Love this! So relatable! Can you also post on what readers wear on Feb 14? It doesn’t have to be about going on dates.

    • Amy says...

      Yes that would be a fun read!

  25. Rosie says...

    I am all about showing skin on date-night. My wife and I both wear suits to work every day, so I love wearing tight jeans and a silk camisole out to dinner. If I would wear it to work, I wouldn’t wear it on a date. My favorite dress for summer dates is backless, and I love feeling my wife’s hand on the small of my back when we cross the street. We don’t get a lot of dates, so it’s nice to make an effort when we go out.

  26. cg says...

    What Tiiu, Kingston, Ontario said…
    How do people know how to pose in a way that looks natural? What to do with the hands and arms? What to do with my legs when it’s full body? How do I create some movement and angles, and find out my “good side”?

    • Nikki says...

      Oh my gosh Jo- can you have an instagram influencer (think cupcakes and cashmere) or model do a post on how to pose in pictures?!?!

    • Joanna Goddard says...

      That’s a fun idea, Nikki!!

  27. Tiiu says...

    My bucket is filled right up! Aiya! Thank you, sweet community of lovely people! You are all very good stuff. Sheesh.
    (Yup, Squatty Potty.)
    (That tub is 👌.)
    (The outtakes from this photo shoot are pitiful. My hands! Runner up to this photo was basically jazz hands. Thank you for the hands in pics advice.)
    (Geez, these ladies are beauts!)
    (Joanna! Look at you go, you connector, you! Pats on the back, hugs, and high fives.)

  28. Mimi says...

    Thank you to these lovely women for sharing! and to COJ for the idea. I am SO sick of lifestyle bloggers posting date outfits that just do not work for the vast majority of people! Dates happen in the dead of winter, where public transit or walking is involved…thank you ladies for your HeatTech, fuzzy sweater, adorable walkable boot ideas!

  29. Anna says...

    Love Jillian’s pictures (and picks – great gear!). We’ve had multiple days trekking in beautifully wintery weather this week in the PNW, and I could sure use some better gear. ;)

  30. Jennifer Taber VanDerwerken says...

    This was just the nicest thing to be part of… I loved all the other women’s looks and thoughts, and this community is so filled with positivity and support.

    And Tiiu—I never know what to do with my hands either! I always want a prop of some kind. Cup of Jo tutorial on what to do with your hands in photos?

    • Beth says...

      Jennifer! I love your top or dress – it looks gorgeous with your hair color! Would you share where it’s from?

  31. Janey says...

    These are all adorable! Made my day!

  32. Abesha1 says...

    The diversity in the models of the Karina dresses (which are new to me) is STUNNING.
    Love.

    P.s. Joanna… you took down yesterday’s post?

    • Joanna Goddard says...

      yes, because i agreed with the reader feedback, but i can put back up so the thoughtful debate is still up there. posting now!

  33. Gilly says...

    I wear a white lace top, blue Madewell jeans, and black leather combat boots. The lace makes me feel pretty and the boots make me feel tough. And like 3 inches taller!

  34. Claire says...

    I also want to know what everyone wears to the grocery store when you are convinced you won’t run into anyone you know.

    • Gilly says...

      Sweatpants/sweatshirt in two different shades of grey, tan Walmart knock-off uggs, all of my hair on top of my head like a Telletubby antenna, and a scowl. If the sweatshirt is already going in the wash afterwards, I do not hesitate to use the sleeve as a Kleenex.
      And yourself?

    • jules says...

      I always feel like I can wear any mismatched style or colors of sweats if I put on a big scarf and my glasses. Instant weekend-chic and hidden from all Trade Joe acquaintances! My husband thinks its funny to go out wearing all grey like a 1990s track-suit-dad so I have reason to hide…

    • anonymous please says...

      Ratty hair in a messy upsweep, pajamas that look like pants, slip on shoes that are a bright color and a jacket over a camp t shirt so I can skip the bra. Did I just say that out loud?

    • Nigerian Girl says...

      You will run into someone you know, Claire. That guy who ghosted you? Yes. So, be prepared. Throw on a great pair of jeans, a plain white T-shirt, stud earrings and sneakers. If you want to look very pulled together, wear lipstick as well. I’m a Nigerian, a Lagosian at that. We never dress down :)

    • Sandra says...

      Me too!!! Except we moved from Chicago to a small town so it is pretty much guaranteed I will see someone I know every time I leave the house. Good and bad for sure! I would also like to see parent school drop-off outfits. Mine are so bad!

    • Vanessa says...

      I agree with Jules. My glasses are usually sunnies (yes, inside the grocery store), I never leave home without earrings – dark hoops for this ensemble – and lipstick over my sometimes unbrushed teeth, depending on my coffee situation. A bra is a maybe and my black Adidas bum bag slung cross body to top off the “look”.

  35. Claire says...

    Kathryn in Kingston- the dress looks terrific and I got a thrill out of seeing it because I grew up in the Hudson Valley and went to high school in Kingston. I have been tempted to buy a Karina dress out of sentimentality, but held off, thinking that was a silly reason to buy a dress. But it looks really good on you in your photo! so maybe I will get one sometime soon.
    Love all the other photos too, all of the outfits are fabulous. Love the polka dot rummage sale sweater!

    • Kathryn Heidecker says...

      Claire, that’s so sweet of you to say! Honestly, I didn’t buy a dress for awhile because they are more than I usually spend on clothes. But I’ve gotten a lot of use out of them. When did you graduate KHS? I’m 2001.

    • Claire says...

      Hi Kathryn- I left KHS, and the Hudson Valley, a LONG time ago (1970’s) to move to Austin, TX. I am guessing that Kingston is probably very different now. I miss the area still, especially in the autumn, and I miss snow.
      It’s nice to connect with you via this post!

  36. Lindsay Somers says...

    Love the diversity in people, bodies and activities in this post. You’ve built an inclusive community. 💛

  37. Colleen says...

    Would love to know where Jessica got those brown boots! They look like my Danskos I live in during Minnesota winters.
    Great style & fun details, ladies!

    • Colleen says...

      Never mind, saw it below.

    • Courtney says...

      Colleen, I’m a fellow Minnesotan wondering the same! I usually go for Sven or No 6.

  38. Rae says...

    This was so fun to read! Love this new feature : )

  39. mado says...

    Second!!!

  40. Jody K says...

    Whoa, Jennifer, Ballstons hubby looks like a grown up Toby!

    • Joanna Goddard says...

      Oh my gosh you’re right! Haha!

    • Jennifer Taber VanDerwerken says...

      Oh wow! I kind of see it! I’ll tell him.

  41. Andrea Still says...

    All the ladies outfits are fab, but Jennifer from New York: please share the brand/shade of lipstick you’re wearing!

    • Jennifer Taber VanDerwerken says...

      I’m so sorry I can’t clarify! It was a free sample from Sephora and the brand and shade have totally rubbed off the tube! It’s just a nice warm pink. (I’m a beauty guide failure).

    • Andrea says...

      ha! Another Andrea coming to ask this same question. It looks lovely.

  42. Lauren E. says...

    Tiiu, I’m dying over here. SAME! I’ve actually realized the dumber I feel taking the photo, the better I look in it. My husband and I stayed home on NYE but got all dressed up, and we did a “photoshoot” with his new iPhone and a ring light, and I struck the most outlandish poses. It’s the best I’ve ever looked in photos! Highly recommend.

  43. Happy, thank you, more please! Love these!

  44. MJ says...

    Love Anna’s outlook after a not so great date!

    • Joanna Goddard says...

      Same! She said she loved being 30 and thus feeling that way :)

  45. Lisa says...

    Costco socks!!

    Also, Anna, I am trying to channel Meghan Markle’s style too – I think you did a great job!!

  46. Danielle says...

    To echo everyone else, these are great! So fun to read, thank you all for sharing. I’m inspired to get dressed up and head out for date night!

  47. Kate says...

    I’ve always loved looking at the Karina dresses but haven’t given in to temptation but now that I know they’re made right down the Hudson from me I think I’ll get one and support the local economy! Thanks Kathryn for the info!

    • Kathryn Heidecker says...

      Aw! Hope you enjoy it! The dresses are great quality.

  48. Jonita says...

    I live in a beach town and it’s summer here in Australia. Last week my husband and I went on a date (a rare thing for our expat fam with a 1-year old!). I wore a white v-neck dress with some sparkly wedges (which were actually from my wedding). The dress is nice because although it’s flattering and a little bit gauzy, it’s fitted and a bit sexy (sheer below the knee + the fitted top that doesn’t show too much, but highlights my shape). I felt beautiful and comfortable.

  49. Cathy says...

    Gorgeous! Each and every woman. Love this post.

  50. Beckwith says...

    Jullian; I love your look Jullian’s ‘Real” look! Frosty eyelashes! So pretty! And most of all, the clothing recommendations – I’d never heard of Dovetail, but those pants are right up my alley!

  51. T says...

    Each of these women is so radiant and beautiful — love everyone’s style so much! Totally inspired. Thank you!

  52. Julie says...

    Love this…can I put in a request for “what readers wear to weddings?!”

    • Nikki P says...

      Yes please! A bit of a global picture on this would be great!

    • Joanna Goddard says...

      Yes!! What a great idea!

    • Sarah says...

      Ohh I love this idea!

  53. Teresa says...

    Aww, thank you so much!

  54. jami says...

    I want to be friends with “I don’t know what to do with my hands.” LOL

    • Sadie says...

      I don’t know what to do with my hands either.

    • Amy says...

      Great post! Love the different styles.

    • Agnes says...

      I so love the costco socks along with the gold high heels. That pretty much sums up Canadian style for me as a Canadian, hahaha!! (Says the one who wore snowpants to walk to work in -33C/ -24F today). I feel you girl! And you look good!

  55. Amee says...

    A big shout-out to Divya from Mumbai! Is that a t-shirt you’re wearing with a saree? I miss wearing saree out here in the U.S.

  56. Mimi says...

    I heart Lauren’s “I like to remind him of the fox he married.” Also, I was so sad to read Teresa’s sweater was vintage. I want that sweater!!!

    • Jess says...

      Same! Already browsed Etsy lol

    • Joanna Goddard says...

      I loved that line too, Mimi!

    • Lakshmi says...

      Haha same! LOVE that line…I’m going to tell myself that every time I get ready for date night now.

  57. Marti says...

    Anna from Hamburg, where is your monogrammed bag from? Love your style <3

    • Katie says...

      I’m not Anna, but it looks similar to the transport totes from Madewell! I know they offer monogramming. Hope this helps!!

    • jillian bedell says...

      Yes! Anna from Hamburg is my new style icon.

    • Anna Allen says...

      Great eye, Katie! Yep! Madewell! They wouldn’t ship it monogrammed so I did it when I was back home visiting Kansas City! I love the bag!

    • Emily says...

      Anna from Hamburg, same question but for your nail polish! Love that red!

  58. Gro Amdal says...

    I highly recommend going jogging or take a brisk walk before the date. You will arrive with roses in your cheeks and a twinkle in your eye. This is what you wear:)

    • Cooper says...

      I love this! I biked to my first date with my now-husband, since we were meeting at a cafe not far from my house, and I didn’t realize the route was basically one long uphill stretch. I arrived all flushed and sweaty, which made me nervous, but my husband still talks about how cute I looked that day :)

    • Tenley says...

      Haha, my mom used to call makeup “liquid exercise” because it gives you the same pretty, flushed look, without the physical activity part!

  59. P says...

    Love this! I want to be friends with Tiiu! Love her shoes and the entire outfit in general, plus I too am tall and often don’t know what to do with my hands!

    You should do a post that showcases what women wear for dates with their besties, or ladies nights, or some such. I notice I put WAY more care, and spunk to my outfits for my girlfriends, and just a little twist for my dates with hubby. For example, he likes me in skinny jeans, I will wear them for him, but that is SO boring and “basic”. For my girls, I will sometimes wear an architecturally interesting necklace, or wide legged pants, or some crazy jumpsuit with chunky moto boots, and I know they will love it! I feel that women dress for other women. Or maybe it’s just me!

    • Maura Kenney says...

      I second this suggestion and agree wholeheartedly!

    • jillian bedell says...

      I dress for women – I undress for men. I think Lauren Bacall said that?

    • Kris says...

      How about a post showcasing women who date women? It would be interesting to see how the outfits are similar and different.

    • AN says...

      @Kris, why assume this wasn’t that post? More than half of the women featured above don’t mention anything about their date’s gender. Like my ex used to say “I assume everyone’s gay unless told differently!”

    • Kris says...

      @An, very true and an excellent way to look at the world. I guess I meant it in response to P’s observations about what they wear to go out with women being different from what they wear to go out with their husband. I’d like to hear from women and non-binary folks about the experience of dressing for women who are also romantic partners, not necessarily in contrast to this post but in addition to it.

    • Kelly says...

      Yes! My boyfriend just “doesn’t get” certain fashion things. When I go out with my girlfriend (I’m polyamorous) or girlfriends (girls who are friends, ha!), I’m much more likely to wear my eclectic vintage, bold prints, interesting jewelry, and yes–wide leg pants/jumpsuits!

  60. love Tiiu’s very Canadian style that revolves around thermal underwear!!! She does a wonderful job of making it looks styled!
    Love to see more of this, real people posts. very relatable.

    • Just in case Tiiu reads this – I’m the same, and I”m a photographer! I never know where to place MY hands in a photo, but I always tell my subjects – have a “fun” moment when they get stuck – twirl around, put em in the air, throw them on your hips…I”m just terrible at taking my own advice!

  61. Daniela says...

    My hubby and I honestly don’t go on many dates. I worried about this at first but then realized to each their own!

    We love getting groceries together then going home to cook, doing puzzles, cuddling in bed watching Netflix, and just spending time around each other at home. When we travel (which we love to do) it’s a different story and we’ll go out, then I like a sexy dress or jeans and a top, and of course a swipe of lipstick.

    • Joanna Goddard says...

      That sounds so nice!

    • Lilly says...

      My husband and I do go out on many dates, because at home our children don’t give us time to even talk! I love when we finish our date with a quick grocery shopping trip. Sometimes grandma takes the kids and we stay home to watch Netflix, cook or play a board game. So, our dates sound very much like the dates you don’t have (=

    • Daniela says...

      Lilly, love your perspective on this. I guess in a way they ARE dates since it’s quality time we spend together – home dates? :)

      PS hi Joanna!

  62. Liz Coppez says...

    Can Jennifer Ballston please share her make-up? I’m looking for blush and lipstick in those exact colors!

    • Jenn says...

      The blush I know! It’s elf—a cream palette in warm tones and I mix them together. I only ever use cream blushes. If anyone has any other recommendations, I’d love to hear them!

  63. Jordan says...

    Where are Jessica’s boots from? They are darling. I would love to own a pair~

    • Jessica says...

      Thank you! 😘 They’re the Odessa Clog Boots from Frye. I got them on sale at Anthro in the fall!

    • pearl says...

      thank you for asking that! those boots are crazy good!

  64. Sara says...

    I loved this! Can this happen every few months?

    • Joanna Goddard says...

      Yes!

    • shannon says...

      I agree wholeheartedly! Fresh ideas for each season!

  65. Asia says...

    What a cute post. I love to be reminded that CoJ is made up of a community of regular women, all beautiful in their own way.

  66. Luísa says...

    this should be a regular series!!! these women are BEAUTIFUL

  67. Jackie says...

    I love our people!

  68. Erin says...

    My favourite date outfit is leather leggings, a big sweater, either boots or sneakers, depending on the date, and a smoky eye. I like to hit a point between sexy and comfortable.

  69. Eli says...

    What beautiful women!! The glow coming from them has put the biggest smile on my face while reading this. :D Love this post and love seeing other readers! Excited to check out the linked brands.

    Newly divorced, I am starting back into the dating scene (I’m 32 and haven’t dated since I was 23!!!) and Im finding that I am wearing what I feel my best and most confident in – favorite jeans, motorcycle boots or heels, a white button down or tee-shirt and a blazer. Quintessentially me and it makes me so happy. Plus a great red lip because nothing makes me feel my best quite like that. I tell myself if the person I am on the date with doesn’t like what I’m wearing and the vibe I’m giving off – they just aren’t for me anyway. What you see is what you get and Im always trying to present myself as authentically as possible.

    • Ro says...

      Same! I’m always tempted to wear something “date worthy” like a flirty dress or a skirt and heels. But that just ain’t me! I’m going to show up in all black with big boots on, and maybe even an oversized sweater or my favorite big “ugly” coat. And if they can’t handle it, or think I don’t look girly enough, so be it! The right person will think I look cool as f**k, and pretty, no matter what I’m in :)

  70. anna maria says...

    love this post. what beautiful people <3

  71. Kari says...

    I LOVE this post! So fun to get outfit ideas and also feel like I’m getting to know some lovely COJ readers! xx

  72. Rebecca says...

    Yes, where is that floral blouse from and what color lipstick is she wearing in the first photo? Love it!

    • Jenn says...

      Hi! Top is Ann Taylor and the lipstick is (I kid you not) a free Sephora sample whose identifying information has long since rubbed off. I wish I knew so I could replace it!

    • J says...

      The top is from LOFT

  73. Kristin says...

    Love that vintage sweater, Teresa!

  74. Sequoia says...

    Oh my gosh Teresa your on my street! It’s so cool to see a fellow COJ so close by! Love the sweater!

    • Sequoia says...

      *you’re

    • Joanna Goddard says...

      i love this!!!

    • Teresa says...

      Oh my gosh, what are the ODDS?! Adam’s Point neighbors unite.

      Wave me down if you ever see me/want to get coffee. xo

    • Sequoia says...

      Does waving you down on the internet count? Maybe Joanna an send you my email.

      Also, Joanna I met you at Clare V event SF. Very pregnant and very worried about becoming a boy mama. You told meet him and I wouldn’t have any idea what I was worried about. Well you were right. Maybe you could do a follow up post about boy mama’s. I have a lot to share!

      -Does anyone else feel really cool when Joanna replies to their comment?

    • Jillian says...

      Sequoia and Teresa–that is my street too!

      I am out walking my dog around Adams Point daily, so I have a feeling we have all seen each other at some point. Now I will know to look out for that amazing sweater!

    • Teresa says...

      Aah, yes I hope I run into both Sequoia & Jillian someday soon! And Jillian — I also walk my dog around Adam’s Point on the daily. If you see me with a small black dog named Ike (currently wearing sweatshirts constantly because he gets cold), say hi :)

  75. Angela says...

    Lauren- fellow Hoosier here! You took the words right out of my mouth. I NEVER wear makeup to my techy job, typically rocking a messy bun or pony to boot. However, my kids think I am a literal goddess when I put in any effort. Just wore lipstick (FOR THE FIRST TIME!) to a family date and my kids were swooning! I love that wearing my hair down and putting in a little effort is considered fancy by 4 year old standards.

    • Sarah says...

      Ha! Whenever I straighten my hair, my 7 year old daughter nervously asks, “are you going on a date with daddy?” Guess I don’t make much of an effort most of the time…LoL!

    • Rebekah says...

      So cute. My four year old daughter is seriously the best boost for my self-esteem. I don’t think anyone else even notices when I wear a lip stain and hoop earrings, but she’s the first to tell me that I look “vewy beautiful” 😊😍

  76. Christina says...

    oh. my. gosh. I love these women! Their responses make want to go out for a girl’s night with them, haha!

    • Joanna Goddard says...

      same!!!

  77. Annabelle says...

    I like Anna from Hamburg’s style; it’s so sophisticated. It would be cool to see an apartment tour of her place here, too. (From a reader in Europe; I’m sure there are lots of us)

    • Chrissie says...

      Yes I want to see Anna’s apartment!!

    • Mareike says...

      Yeah, I would love that, too! Apartment tours in and around Frankfurt/Main? – Got my camera ready. :)

    • Anna Allen says...

      Oh my gosh you brightened my day! Much needed from a rainy dark Hamburg!!! I’d be honored to share my place @cupofjo! ❤️

    • Jessica says...

      I was also most intrigued by Anna!

  78. Elspeth says...

    I love how real this post is. I love all the photos on Cup of Jo, but these feel a bit more authentic in a way since they are just women living life (and looking fabulous!). Wonderful styles from all of them and I like seeing people’s homes in the background haha 💜

  79. Angela says...

    I want to be friends with Teresa, lol! Love that she dresses for the possibility of having to climb a fence. For dates with my boyfriend, I almost always wear a sundress with sandals (I live at the beach in Florida). If it’s chilly, I’ll wear jeans and a cute top. For more casual outings, I often wear denim cutoffs and a tank top or my yoga gear, which makes me feel ready for anything!

    • Teresa says...

      I would LOVE to be friends with you, Angela. And I love your casual beachy date outfit philosophy. There’s nothing better than feeling comfortable & ready for anything.

  80. Ashley says...

    I need a tour of Anna from Hamburg’s apartment, stat!

    • Anna Allen says...

      BLUSHING! (I’d be HONORED.)

  81. Megan says...

    For some reason, these photos and stories of beautiful women from all over the world made me teary eyed. The thought that we’re all just trying our best, putting on eyeliner and going to farmers’ markets and enjoying a walk on the beach, in Oakland and Ontario and India and Indiana… It’s really something, isn’t it?

    • P says...

      same same. i just thought i was emotional today. but it is something to think we are all so similar in our little ways.

    • Kari says...

      I second this! Feels really special.

    • Em says...

      I agree Megan! So much beauty in the world :)

    • Amy says...

      Agree and love this community of women!

  82. AN says...

    What I wear on dates is neither here nor there when there are deets to hopefully learn about Anna from Hamburg’s sexy-as-hell flats, what are they, please and thank you!!!

    • Anna Allen says...

      Oh my days, thank you!!
      9 Euros from H&M on sale!!!! (You can take the girl out of the Midwest but she’ll still yell the price of something and where she got it after it’s complimented! LOL)

  83. Meigs says...

    okay that polka dot sweater is EVERYTHING <3

  84. Amy says...

    Could not love this more! What radiant women you all are!

  85. Lisa Saffer says...

    Jennifer from NY, I need to know what that wonderful print is. Dress? Shirt?

    • Jenn says...

      Hi! It’s a top from Ann Taylor (that I literally ran out and bought just before our date because I hated everything in my closet). It’s from last summer, so I don’t know if they’ll still have it. ❤️

    • Rachael says...

      Yes Jennifer! Please Share!!!

    • Dawn says...

      Also, would Jennifer share what lipstick she’s wearing?? I adore this style segment. What a fun glimpse of each woman’s lovely, unique personality!

    • Amanda says...

      Hear, hear!

    • Lisa says...

      Yes, Jennifer. Your look is awesome and I love your eyes and smile!

  86. liz says...

    CUTE! More of these kinds of posts please <3 <3

    to answer your q, I've been with my boyfriend for almost four years and I've noticed a big difference between outfits I wore on dates when we first met and what I wear now. I played it safer when I was getting to know him — more feminine outfits and conventionally "sexy" but not too aggressive looks. Nowadays since the comfort level in our relationship has been turned up to max, I feel more comfortable being true to my style and I honestly don't give an f about whether I look conventionally attractive (although I think I do!) You can often find me in some sort of big jumpsuit or wearing more interesting silhouettes that aren't necessarily meant to make you look like your tiniest, etc. Being adventurous in my style without worrying about being "attractive" in the way a typical guy would define it has been so liberating. It kind of reminds me of the origins of the name of the blog "Man Repeller"! lol Just wish I felt more comfortable to dress like this on dates from the beginning.

  87. Mara says...

    I’d love to know where the beautiful floral blouse is from in the first picture, please! Great post :-)

  88. LJ says...

    Can we do a style post with Tiiu from Kingston, Ontario? I love her neat style!

    • Becca says...

      Yes! Plus she’s from my town ;) Wow, so cool to see someone from Ktown featured on COJ!

    • Michelle says...

      She looks adorable!!!!

    • Laura says...

      And can we please talk about her amazing bathtub???

    • K says...

      And I spy a Squatty Potty in that bathroom! Our doubles as the foot stool for the kids at the sink. Small bathroom and it tucks under that toilet so no one trips.

    • Tiiu says...

      Hello K-Town buddy!
      (And, thanks a bunch, all!)
      Squatty Potty Lovers: Do you know about the “Tushy”? https://hellotushy.com/