Three Date Outfits

Three Date Outfits

Last week, we talked about first date venues, but arguably, a more pressing issue is dating attire. It can be tough to strike that balance of looking like you tried… but not too hard. In light of this, we devised a real-life sartorial choose-your-own-adventure. Here are three different date looks — which do you prefer?

LOOK #1: Sleek & Sexy
Three Date Outfits

Have you ever been intimidated by an item of clothing, only to try it on and discover it’s your new best friend? This skirt is like that. It’s surprisingly flattering, and feels sophisticated and edgy at the same time.

Three Date Outfits

In my twenty-something, Carrie-Bradshaw-emulating days, I spent far too many nights tottering around the city in heels. But dates are supposed to be fun. And you know what’s not fun? Pinchy toes.

Three Date Outfits

So these days, I choose flats. You never know where the night will take you: rooftop drinks, meandering walks, impromptu bowling… It’s nice to have shoes that let you frolic, should the mood strike.

Three Date Outfits

A denim jacket keeps it casual, with just a hint of tomboy.

(Sources: Skirt, camisole, jacket, vintage bag, heart ring, oval ring, shoes)

LOOK #2: Laidback & Playful
Three Date Outfits

This look feels the most flirty and feminine of the bunch. The crystals say, “I care! I dressed up for you,” while the T-shirt says, “but in a casual, non-committal sort of way.” Plus it’s comfortable as can be.

Three Date Outfits

I love how these look like ballet shoes, but the pointy toe keeps them feeling fresh (and not too precious). Plus, pointy shoes elongate your legs (a must for my five-foot-tall frame).

Three Date Outfits

Last but not least, “The gemstones draw attention to your boobs,” my friend helpfully pointed out. So, there’s that.

(Sources: Tank, jeans, shoes)

LOOK #3: Casual Bohemian
Three Date Outfits

When it comes to dates, my philosophy is to wear what puts you at ease. Dating is awkward enough without clothes that leave you tugging, itching or watching how you sit.

This outfit is the closest to my everyday jeans-and-tee uniform. Because what could be comfier? A silk tank elevates boyfriend jeans, while a vintage necklace and statement shoes make it feel like a proper “outfit.” Quoth the wise Jenna Lyons, “As far as I’m concerned, leopard is a neutral.” (You can see all the colors here.)

Three Date Outfits

And of course, a swipe of red lipstick provides the finishing touch.

Three Date Outfits

Yay! Dating.

(Sources: Camisole, vintage jeans, vintage necklace, ring, shoes)

So, please tell me: What do you wear on a date? Which look is your favorite?

(Photos by Nicki Sebastian for Cup of Jo. This post is sponsored by J. Crew, a brand that has hung in our closets for years. Thank you for supporting the brands that support Cup of Jo.)

  1. Thanks so much for featuring our Heart Ring!!! You are too sweet and beautiful!!! Love you!


  2. Sarah says...

    #3 for sure! It’s casual but also dressy enough with the cute flats, jewelry and black top for a variety of venues. It’s not over-powering so the true focus becomes you you – not the outfit.

  3. Addie says...

    Please help! I adore the jcrew Carrie cami look, but have no idea what kind of bra (if any?) you would wear!

  4. Love the last outfit! The bright lipstick steps it up. Color looks great on you!

  5. The third outfit is just the right amount of casual and chic. Love it!
    Wearing something that doesn’t flatter you, or makes you feel uncomfortable is not a right choice for a first date.
    As long as you’re comfy, everything works well!

  6. The ripped jeans and animal print shoes are by far my favourite. Great style and so simple.

  7. Jenna says...

    Outfit #2 is my usual, but I’m surprised you said you always wear flats! As a fellow five-foot-tall woman, I always wear a shoe with a bit of a heel or wedge because how awkward is it trying to talk to someone who towers over you, especially if you’re standing at a bar? I really think the distance makes it feel a little awkward and a little harder to connect.

  8. I love the last two. You can get into places by just looking dressed up not do much dressed to the nines as they say.

  9. I think we can all agree that Caroline is the absolute cutest.

  10. JT says...

    I am a feminine kind of girl with spunk. So it would be outfit #1 with leopard flats from #3. Probably a vintage black Coach crossbody bag.

  11. I love #2 and #3 — though you look so great in all of them, Caroline! I’d probably like to wear #3, but the truth is that wearing a strapless bra on a first date would probably make me fidgety and uncomfortable, so I might go with something more like #2 :)

    And good luck in the dating world! That can be so tough…

  12. Katherine says...

    I looooooove the look #3. Definitely a winner!!!

  13. Looove the skirt in look #2, they all suit you so well!

  14. Molly B says...

    Look #2 for the win! (But swap the shoes for the leopard prints from Look #3 :)

  15. second outfit is my favourite:P

  16. They are all great looks but I think I’ll opt for chic bohemian xx

  17. My vote is for number 1. Dressed up enough but not too dressed up. Yes to the flats and skirt. The others look too casual. And yes to the lipstick, always yes to that

  18. Nice choices, my fave is definitely number 1 though. So pretty!

  19. jen says...

    I vote for number 3. Looks comfortable and still sexy. Though I am old/old fashioned and even if I like the jeans, I still don’t go for holes. I am almost 40 for the record…

    Hope you find someone who brings out the best in you no matter what outfit you wear.

  20. Ariane says...

    time to go shopping i think. thanks for this it’s always so hard to figure out what to wear in this kind of situation

  21. Michele says...

    I love this blog, but did anyone else feel a little like feminism took a hit with ““The gemstones draw attention to your boobs,” my friend helpfully pointed out. So, there’s that.”?

    • Emily says...

      I got the vibe that it was a throw-on complete shirt, with the necklaces already placed on. Felt like it was more convenient than boob zoning. That’s just my look on it though :-) xx

    • Erin says...

      Nope. Feminists have boobs and pay attention to the world enough to know that, yes, lots of men like to look at them. Pretending that’s not true is just… pretending.

  22. Outfit number 3 is my favorite. You look amazing in all three, but the last outfit gives you an effortless confidence.

    Have fun on your date!

  23. I will have to say that number 1 is my favorite. I am all for going a little more feminine for a date. The problem for most girls id feeling comfortable, so in that case the simple tank with denim is a great choice.

  24. Stephany says...

    I actually like #1 the best! I’m surprised it’s not getting more votes. I think there’s something to be said for looking like you tried. What’s wrong with that?!? I think it reads, “I’m a feminine woman who is SHOWING UP for this date,” versus, “I am desperate and trying to hard.”

    I also am a fan of heels. I think that immediately when you walk in the room and see him (or her!) with those heels clomping underneath you, it sets the tone that you are, in fact, a total f*cking babe.

    Plus, they make your legs look Taylor-Swift millions of miles long!

  25. Aga says...

    ““The gemstones draw attention to your boobs.” So, there’s that.” – I love this blog.

    I never shop at JCrew but I want that skirt! The 3rd look seems most “you”, the necklace is amazing, and you wear lipstick so well! But I was always weary of bright lipstick on the first few dates. I would worry about it fading or being on my teeth after reapplying or smudging, like, say during a kiss. :)

  26. Cynthia says...

    I like the second and third looks. I have never understood the ripped jeans look. I guess it goes back to my childhood many years ago. If you wore torn or ripped clothing, it meant you were very poor and your mother didn’t own a sewing machine to repair clothes. I love dark wash denim because it looks dressy and, in my case, it’s slenderizing. I’ve always been a big fan of flats.

  27. Love the 3rd one! I love dressing up outfits with my leopard flats :)

  28. Joanna says...

    Please tell us what lipstick you’re wearing. In the pictures, as least, it looks like the perfect blend of a red and a pink. Thanks!

    • Caroline Donofrio says...

      Of course! It’s MAC Ruby Woo — quite possibly the best red ever.

  29. I’m definitely feeling ripped jeans these days, so #3 for sure.

    xo The Analog House

  30. wkwr says...

    I love the third one. That necklace!

  31. Caroline is gorgeous! J Crew is such a trusty standby for amazing basics!! Love them all, but that last one is the epitome of relaxed cool! xo


    adorn la femme

  32. Carolyn says...

    You are young and beautiful. Wear the jeans and camisole with leopard flats. I am not a fan of the necklace. To me, it’s a bit serious for the outfit. How about delicate, layered gold necklaces and a leather jacket. Your lip shade is amazing. Have fun!!

  33. I love both #2 and #3! And hooray for being petite! It’s so refreshing to see clothing options on someone my size. I’m glad J.Crew has improved their petite collection lately, as I find it nearly impossible to find clothes in my size these days. There’s a lot of us out there, so I think we deserve a bit more attention :)

  34. Andrea says...

    My only rule for first dates is never wear a new article of clothing. There’s nothing worse than leaving the house looking cute as hell and then finding out mid-way through dinner that your shirt makes you sweat profusely.

    • I second this! I once wore a top with this cute sequin lining. Ten minutes into the date my date said, “Um–you’re bleeding.” I looked down and there were all these tiny cuts in my upper arms–the edges of the sequins were so sharp they were making me bleed! Needless to say I do not wear that shirt anymore.

    • Meg says...

      I ABSOLUTELY AGREE! There’s nothing worse than being uncomfortable on a date, as everyone has already said. New clothing is such a gamble! (New shoes even more so!)

  35. Love all 3, but you look the most amazing in the third one! And I LOVE the red lip. I’ve been on the hunt for the perfect red lip lately, and I think I’ve settled on MAC Red… :)

  36. Christy says...

    Love the flats!!! I am done with heels after wearing them for 6 hours at a wedding last weekend. Been paying for it, blisters and pain, ever since. Great outfits, she is a stunner.

  37. All very cute but the third is my favorite! The leopard shoes add a pop to the look

    Meet Me in Midtown

  38. caro says...

    i’m torn between 1 and 2! i’d try on the skirt from 1 and the tank from 2, and make that work, haha. also, i’ll take the shoes from 3 for another outfit!

  39. I think I like the third outfit the best. Something about it is so casual, yet sexy. Dating outfits can be such a hassle though.



  40. Danielle says...

    I like the three outfits very much but would choose the first one. I love the skirt that paired with the denim jacket makes you look effortlessly stylish.


  41. Wow, I love that jeweled tank from J. Crew. For first dates/newer dates I would always meet up with them for a drink after work so usually my date outfit was just my work outfit. I’d usually make sure to wear a dress but it was work appropriate dress. If it’s a daytime date in the summer I like to wear a sundress with a sweetheart neckline and feminine print like polka dots or floral. In the fall/winter skinny jeans and a cute sweater. This description is pretty much I wear what I wear most of the time regardless of whether being on a date.

  42. Casey says...

    Caroline – you look adorable in all three, but I vote for the second choice. Comfy, cute, and casual. Have a fun date! Can’t wait to hear about it. xo

  43. I have always sworn by the “jeans and black tank top” uniform. Works every time! It is the perfect combination of sexy and tomboy.

    Good luck, my dear!

  44. Shannon says...

    As a fellow woman, I’m guessing close in age to Caroline, also newly re-entering the dating scene, I just want to say how much I love these dating-related posts! And you have such great style. I love all these outfits.

  45. Nicki says...

    Love all the looks but the second and third are definitely my favorite since they’re fun and flirty, just the right amount without being fancy! :) As someone who’s 4’10” – I seriously GET IT when it comes to being short. The nice part is I’ve dating a wide range of guys, from 5’5″ all the way to 6’2″! (My boyfriend is 5’7″ which is actually the perfect height for me, I fit exactly under his chin and it makes for the BEST hugs.)

  46. Jennifer says...

    You are so cute in generale and look awesome in all there but #1 is my fav. Feminine with out trying too hard.

  47. I love that lipstick! Does anyone know where it’s from?

    • Yes – She replied to an earlier comment that it’s MAC Ruby Woo!

  48. Aimee says...

    Longtime reader, first time poster. I love these looks. Easy but cute and stylish.

  49. JPB says...

    #3 definitely.

    I agree with not wearing heels. I didn’t think people still wore ballet flats though (especially with a bow on top – never been my favourite). Maybe that’s just all those hipsters here in Berlin with their Birkenstock ;)

    • Olma says...

      Heehee! I love that Berliners don’t wear heels but at the same time it is certainly not a very fashionable city. I think these pointy ballet flats are very on point fashionwise.

  50. Toun says...

    I’v just send a post : i’m sorry for my english, i’m french (that’s no really a excuse)

  51. Victoria says...

    Caroline is stunning.

  52. Leticia Centeno says...

    I love all 3 looks but Caroline looks the prettiest on the last one.
    It has that I woke up like this feeling :)

    I’m a big fan of flats. I use them everywhere to any ocasion. Really.
    I think I don’t even know how to walk on heels anymore.
    Also to me, flats are more feminine and delicate than heels.

    Love that necklace!

  53. I really LOVE #2 because it’s so casual yet adorable, but if I were to pick one I’d totally wear #3 (because I do, every day).

  54. Natalie T. says...

    I think it depends on the date. I love #1 (sleek and sexy) for well, a sleek and sexy date (an edgy art gallery; a third date dinner). But I love #3 (bohemian) for a first date. You look most comfortable in these photos. Love the leather skirt and the leopard print flats. You could also pair those together! I’d go for a metallic flat for #1 as well. The lipstick does elevate it all.

  55. You look great in all of them, but I LOVE the last one. I feel like I can tell that it’s the closest to your every day “uniform.” You look very relaxed and confident.

    • Kali says...

      I concur. For the exact same reasons. Do you, be you.

  56. Heather says...

    A date??? What’s that??? I’ve been married for almost 10 years and don’t get those too often!! =)

  57. Toun says...

    I enjoy reading each of your posts Caroline even this one althought I like NONE of this 3 outfits for a date.
    First of all, if I have a date, I wear heels such kitten heels or wedges heels. Faux leather is too sophisticated and understood only by girls who know fashion.
    I won’t wear a t-shirt with jeans (outfit 2) but rather chose to wear a blouse.
    I fear that faux leather and ripped jean, leopard pattern scare the guy.
    I wont wear such a decolleté unless i can’t make myself clearer in an other way tu make him understand that I want to have sex.
    I specify that I like every item you wear BUT NOT FOR A DATE.
    But what matters is that every one should wear whatever he likes and feels confortable in !
    Thanks for reading.

  58. Nicole says...

    You look great in all 3 outfits, but there’s just something I love about #2. I need to buy those neutral flats–they’re feminine but the point gives them a little edge.

  59. Good, simple and beautiful….it’s great…like this…

  60. Caz says...

    They’re all super cute outfits and you look adorable Caroline! #3 is my fave. Not a fan of beige so I’d just swap the shoes in #2 for tan brown flats or sandals.
    The skirt in #1 is great – I have a black leather pencil skirt but it feels a bit too vampy, so I love the pleated skirt – the sexiness of black leather without being over the top.

  61. Sally says...

    You are so beautiful Caroline!

  62. I’d say outfit 2 is the perfect mix of smart/casual. Def agree with the flat shoes though x

  63. Cute! The bohemian look is totally my style. :)

  64. Lisa says...

    I have a first date outfit that I always wear – its a dress that shows off my curves without being tight, its SUPER comfy and also a silky material that makes it work in the cinema or a nice restaurant or a bar.. It doesn’t look off anywhere. It is also bright blue and I get a lot of compliments wearing it together with my red hair :) Dates can be nervous enough so not having to think about what to wear is the best thing ever. Oh and flats. I am a big enough girl and don’t like the feeling of being much bigger and taller than someone I’m dating so flats is a must, plus no sore feet or wobbly walks.

  65. Marta says...

    #3 all the way! you are so pretty, Caroline :)

  66. annie g says...

    I love the skirt and think if you put the leopard skin flats with it instead of the black it would look a bit edgier, a bit less matchy matchy. If you walked into a bar like that and I saw you, I would think: what a confident and happy girl! Made an effort but not too much of an effort.
    Please bear in mind I am much older than you, mother of adult daughter but regular reader of Vogue; so am not going to tell you to put on a cardigan and do up a button. I would keep jeans outfit for a Sunday morning breakfast. Good luck and have lots of fun!

  67. I LOVE LOVE LOVE the 2nd outfit, that skirt is amazing!


  68. CATHERINE says...

    From a country where there’s no such thing as dating, it’s hard for me to judge, but I would like to point out #2 & #3 are not that different. I really like you in the skirt, although it could be weird to wear it on a date if you’re a jeans person. I wear jeans all the time, it’s nice to slip into a dress or a skirt for a change. Good luck on the dating scene-I hear it’s tough!

  69. I have to say I liked all 3 outfits, especially the ballerinas… a so girly & comfy choice indeed.
    But I would go for the Playful look. A laid back outfit helps reduce the first date anxiety ;)

  70. #1, but I’d carry the googly eye bag instead!

  71. Gorgeous! I love the co-ordinating shoes. My favourite is the last one – I can see you feel most comfortable in it!

    Now go out and conquer! :)

  72. Natasha says...

    You are such a gorgeous woman, Caroline! Your perspective on Cup of Jo has been delightful for me to read, and fun! I feel like I already have a sense of your style from all that you’ve let on, however I (honestly) feel like all three of these outfits miss the mark a little… I think outfit #3 is my fave, but would be improved by a more interesting bohemian-type necklace, perhaps like this: https://www.etsy.com/listing/211952799/statement-necklace-druzy-necklace-14k?ga_order=most_relevant&ga_search_type=all&ga_view_type=gallery&ga_search_query=statement%20quartz%20necklace&ref=sr_gallery_16

    Or perhaps some sort of strappy, interesting sandals. Ballet flats always seem to be a bit uptight!

  73. Joanna S says...

    You should be a petite size model. Beautiful!

    I’m five-one, and guys joke that I could be their arm rest. What’s a good comeback to that sort of statement?

  74. S says...

    The gray shirt and pants if it was a day date (lunch, museum). The leather skirt if it’s evening drinks or dinner.

  75. I still remember my first “date” with my husband. It was a last minute movie date and I wore my not-very-best jeans and a plaid button-down shirt, not much makeup, and I remember apologizing for my appearance because I hadn’t been feeling well earlier. I said “I’m usually much cuter, I promise!” He said “I don’t think my heart could take it if you looked much cuter than you do now.” Aww! And here we are, almost 10 years later.

    • Celeste says...

      That’s gotta be the sweetest thing I’ve ever heard!

    • Geraldine says...

      Aww that’s so cute! I’m not surprised he’s now your husband.

  76. These are all really cute, but I have to say most of all it makes me happy to see outfits on a woman who’s not 1.5 feet taller than me! (I’m 5’2″, and the struggle is real)

    • Awads says...

      5’2″ here, also. Is Caroline wearing a petite size? It looks too long to be called a “mini”. Just wondering how it would work for my petite build.

  77. Ashley says...

    Ah! Two comments in a row! But I have to ask . . . do you tell your dates about Cup of Jo?!? Do(es) he/they know you are writing about your experience? I’m so curious!

  78. all about the casual bohemian outfit! that necklace makes it.

    midnight snark

  79. Ashley says...

    Caroline! You look beautiful in all three outfits! My personal fave is #2! Congrats to the lucky man who gets to enjoy your company!

  80. Casual, simple and black-based – yes, yes, yes!

  81. AndreA smith says...

    Who makes the jeans in outfit #3?

    • Caroline Donofrio says...

      Hi Andrea! They’re vintage Levi’s.

  82. Trish O says...

    I have not dated since 1997 but I think I will go get #3 for our date night next week. All three are very cute.

  83. Nicole says...

    #2 for sure for a first date. Skirt #1 looks like you’re trying too hard on a first date, and camisol tank #3 means you have to wear a strapless bra which is of course uncomfortable and you’d be constantly fighting with it.

    #2 or any variation of it sets the right casual but I tried and I have style: jeans, blouse, flats.

    Also again I will recommend— first date uniform. Find one that works and use it every time

    • Emily says...

      Agree regarding strapless bra! Maybe Cup of Jo could do a post on those some time??

  84. Oh these are all so lovely! I like the last one the best though, you can really see that you’re comfortable in it and you look stunning.


  85. The third is my favorite, and it definitely shows that it’s the one that you feel most comfortable in! I do however really like the skirt in option 1. I usually opt for a heel, even if it’s a tiny one. A little lift can elevate any look!

  86. Barbara says...

    they are all lovely!
    but maybe one night a simple red dress?!
    hope you a perfect date :)

  87. That jumping picture for the first outfit is rad! I think the last outfit is my favorite, but usually (not like I usually go on dates, but like, when I usually go out for something special) I go safe in an all-black ensemble like the first outfit :) -Audrey | Brunch at Audrey’s

  88. Bri says...

    I really like the third look. May even do grey jeans and pair the denim jacket with it. I love that you mention pointed toe flats elongate the legs! I’m 5’6 but have a long torso and short little legs. Pointed toes and micro wedges are my secret to leaner looking legs!

  89. a few things…
    1) I love your outfit posts the most on cup of jo! real beautiful people wearing real beautiful clothes! you have beautiful photography but so much more approachable than a typical fashion blogger website. thank you for being real!
    2) this is such a great example of a sponsored post that is authentic and real. I could see you actually writing this without it being sponsored.
    3) All the outfits are adorable! can’t chose a favorite :-)

  90. Elizabeth W. says...

    #1! I think the skirt is fun and flirty. The third options are a little too “whatever” for evening. Of course, as we all know from this blog and elsewhere, it doesn’t really matter. If he likes you, then he likes you.

  91. I think I’d go for the third look. But I think the choice also depends on weather and the venue. The first look I’d wear on a sunny walk in the park or to an outdoor concert; the second, to dinner; the third, to coffee or the movies or a museum or as a general fail-safe. :)

  92. Ruth says...

    This is a fun exercise. Definitely 3, but bohemian is my vibe. But you do look most comfortable in those photos too. I love the leather skirt, but not necessarily the all black – I would pair with a different top or shoes.

  93. #3 is definitely my favorite — I’m always looking for something that feels pulled together but comfortable. Fidgeting and pulling at things all night is not cute.

    And not to get too beer commercial-y, but it’s the kind of out look that is up for whatever…dinner might turn into drinks, or a long walk, or midnight karaoke, and this works pretty much anywhere.

    • Emily says...

      You are never too old for red lipstick!

  94. Emma says...

    3 wins! I like what you said about looking like you tried, but not too hard. I think wearing flats instead of heels is the best way to avoid the “tried to hard” thing. If I’m tottling around on heels, I feel like I’m putting on a show and it puts me on edge. Wearing flats makes me feel like I can walk normally and am just being myself on a date.

  95. Susan says...

    #3, you want to be at ease and relaxed and look comfortable!! That will make him feel comfortable (he may be nervous too : )

  96. Super cute outfit ideas.

  97. Lauren says...

    QUOTH!! :) I love you Caroline.

  98. 3! That’s the first time I’ve seen boyfriend jeans and thought, “omg i need boyfriend jeans”. So that’s saying something ;)

  99. Jami says...

    numero uno!

  100. nicole b. says...

    Caroline, you babe. I like the last look best. But you definitely had me clickin’ over to check out that skirt. Nicely done. Go get ’em. xo

  101. Liz says...

    Caroline, you babe!

    Lovin’ that lip color in look 3

  102. Nicole says...

    I like #2, the perfect blend of casual without trying too hard. Comfort is a major bonus!

  103. Gabrielle says...

    Ah! What lipstick is that in #3?

    All three outfits look comfortable and playful :).

  104. Jenny says...

    They’re all winners, but I think #3 is my favorite! Cute + sexy + laid back. I tend to go with a slightly more dressed up version of my usual jeans and t-shirt/tank top uniform as well. I’ll wear my cute skinny jeans (instead of my oh-so-comfy-but-slightly-ill-fitting ones), a slinky and relaxed deep V-neck t-shirt or a cute flowy tank, and a pendant necklace. And ballet flats or boots, depending on the season. I figure it’s doubtful that the guy will remember (or notice) what shoes I’m wearing – but he’ll likely remember if I can’t walk in them or spent the whole night complaining!

  105. Christine says...

    I say always wear a dress on the first date– guys LOVE dresses. A casual sundress, with sandals is the best look for a summer time date. Feminine, but not fussy.

  106. Kara says...

    #3! But you can’t go wrong – you look gorg in all. Keep us posted on the dating life… I love these posts!

  107. Thivia says...

    3! But it also depends where the date is. I love that 3 will still look casual and relaxed with heels.

  108. Katherine says...

    Third BY FAR!

  109. Natty Brown says...

    What bra are you wearing in outfit 3? Love the look, but am a loss for the bra.

  110. Shannon says...

    Gorgeous! Honestly love them all, but #3 if my fave!

  111. Sam says...

    I love look #3! It’s casually sexy, but still looks comfy. Good luck out there!

  112. lindsay says...

    oh! you just reminded me of the black silk camisole i have languishing in the back of my closet….
    i’d love to see even more style posts featuring caroline! we have similar body types so i love seeing her in posts like this.

  113. #2 for a first date, #3 for second date/drinks and when they’ve both gone well, #1 for a dinner date.

  114. I don’t even remember what I wore on many of my dates with my now husband, even though we’ve only been married 4 years and only dated a year before getting married. We had been friends for a long time before dating, so it helped ease a little of the initial discomfort. Our first date was a last minute drive to this big bridge outside of Nashville to see a storm roll in, and he brought me french fries, so it wasn’t exactly a “dress your best” situation. I’m sure I showed a lot of leg through it all though, because if you’ve got it, flaunt it, right?!

  115. I love the outfit with the skirt, but I think they’d all be fabulous on dates. Maybe in order of dates 1,2 and 3!


  116. Jessie Walker says...

    I love the looks, but #3 is the best!

  117. I expected to have a clear favorite, but I like them all! The leather skirt is pretty killer, I love the colors on the second outfit, and I have a real soft spot for leopard print shoes.

  118. Amy says...

    All great looks! I have to say, Caroline makes modelling for these posts looks so natural and easy. Great job!
    It’s a bummer that J.Crew rose their Canadian prices as the dollar is so bad right now. It’s gotten almost completely unaffordable for a regular Joe. (Ie. $143 cami…!)

  119. Molly says...

    I’d wear the shirt from #2 with the skirt, jacket, & shoes from #1! But really you can’t go wrong with any. You look adorable no matter what!

  120. ashley says...

    i’m a skirt kind of lady, so #1 for sure. though i’d probably play up the color casually because to me all black = dressy no matter how comfortable you are. and lipstick. ALWAYS. (also is it weird that i hate pants?)

    in any case, i’m loving this single lady thread running through the blog these days! thanks caroline!

  121. Love these outfits! Simple and chic

  122. christina says...

    i love caroline’s posts, they are always so fun. love all these outfits so much!

  123. The third look is by far my favorite!

  124. Denise says...

    LOVE look #2 – perfection.

  125. Laura Paige says...

    Number 3 is my go to!

  126. I’m no longer dating ~ been in a relationship for 14 years so it’s basically sweats & tees 24/7. ;)

    But I did want to say that your outfit no. 2 is my favourite! It’s so flattering, smart & the pop of color on the t-shirt rocks, you look marvellous!

  127. Nina says...

    You are gorgeous! I like the 2nd outfit best. I would wear something similar.

  128. I love that the sexy look is still comfortable. Flats are always the way to go. No guy wants to hang out with a girl who complains about sore feet. Great choices!

  129. Ingrid says...

    I love all three looks! If I had to choose only one though, that “leather” skirt seems like it would work for any type date, and look casual OR dressy.

  130. alexis says...

    You are stunning! Great outfits.