Three Dresses: Which Would You Pick?

I sometimes dress like a 4-year-old boy (literally), but then I read a quote somewhere that it’s just as easy to wear a dress as it is to wear shorts and a T-shirt. And so much prettier! So, we thought we’d share a few favorite dresses, and the lovely Hadar agreed to model. Here are three looks…

Tomboy: This effortless linen dress looks good even when it’s wrinkled, making it perfect for bike rides and weekend getaways—or cheese shopping at Murray’s. We discovered it at Lou & Grey, a new line at Ann Taylor Loft with really lovely basics. (Sandals from Madewell.)

Feminine: This silk maxi looked like a watercolor painting as Hadar strolled down Bleecker Street. I loved how flowy and eye-catching it was—with two flirty slits—and it would be beautiful for a brunch with friends or dinner in a garden. (Sandals from Target.)

Sexy: All my friends swear by James Perse jersey dresses—you feel like you’re wearing a T-shirt, but you look a million times sexier. This black dress, with ruched sides and a slim fit, would be gorgeous for a date night. (Sandals by Splendid, also available in this fun color.)

Which dress would you choose? Which suits your personality best?

(Photos by Julia Robbs for Cup of Jo. Thanks for modeling, Hadar!)

  1. Ana Leonor says...

    Black definitely!

  2. Melissa says...

    Amazing style and love your recommendations. The Splendid sandals you paired with the black dress, are they a camel color or cantaloupe?

  3. Well, they black dress is great (but I think you may need a body like hers to wear it) – they are so …

  4. AK says...

    Would love to know the lipsticks Hadar is wearing? Such pretty pink and red shades!

  5. Oh, goodness…I couldn’t possibly choose. Clearly, the answer is all three! Though I confess, I do wish that first dress would work a little better for those of us with curves.

  6. I actually bought the black dress after reading your post. I’ve been hunting for a “go-to” little black dress and rolled the dice on an impulse. I LOVE IT. I want to wear it everywhere, with everthing, all the times. I’m counting down to a wedding next weekend and can’t wait to wear it with some strappy heels. Thanks!

  7. Okay joanna I love you–my wallet doesn’t, but I do! I went right out and bought dress number one and wore it today while out running errands with my two boys (6 and 3.5) and I got SO many compliments!!!!! It really made my day. When the hubby got home he said, “I’ve never seen this one–I like it!” Score and thank you!

  8. I’m surprised by how many like the grey one! I think I’d feel frumpy in it. #2 is probably more “me” (bc of the colors), but #3 is lovely.

    I agree with Julia and Jennifer – all I wear in the spring and summer are dresses. Like, I dread when I have to pick out pants again. :(

  9. The gray, definitely.

  10. I agree! Dresses are just as easy as shorts or jeans and a tee. I was just about to suggest James Perse when I reached the end of the post and read your note about your friend’s recommendations. I think their dresses are perfection. I especially appreciate the just-below-the-knee length.

  11. The black! The black! The black! Now if only I could have that hair too…

  12. I always like your fashion posts, but it would be great if you would consider sometimes using models who aren’t skinny and super-conventionally attractive.

  13. They are all pretty! I love the ease of the second one, but I think the first is the most flattering. I would wear the third one to a party, it looks so pretty and flowy. Of course, I imagine myself in them about 20 years ago and they all look terrific!! xoxo Your blog is the best.

  14. Well, we are OBSESSED with James Perse, so that’s a shoe-in… but would wear stripes all day everyday if no one had anything to say about! So torn!

  15. They’re all gorgeous and look super-comfortable, and I’d wear all three (but I might cinch in the gray striped linen one). I’ve been living in maxi dresses this summer, they keep me cool and comfortable with this baby bump I’m rocking (I’ve been in love with them already, so I’m adding ones I’d wear anyway to my collection using maternity wear as an excuse, haha).

  16. I love the first one. A simple dress is my favorite comfy day out outfit.

  17. i would LOVE LOVE LOVE to know how to do her hair!!!!

  18. I have to go with the silk maxi. But, I may be bias as I have that dress too. Love it!

  19. I live in dresses and can honestly say that I would wear all three! I am rather tall for a woman (6’2) and often find with shorts that between the rise and length options, things can look a little…well…scandalous! So dresses it is :)

  20. That black dress is a knockout! But they’re all lovely.

  21. Ran right out and got the Loft blue and white one. It’s perfection! Thank you for a perfect summer throw-on and get out the door outfit :)

  22. The linen one for my free time, the black one for all opportunities ;) they’re great

  23. I am short, round, and flat…this means all dresses look like maternity dresses or flour sacks. I have zero style! Capris and the lightest top I can find..mostly in black or gray! I will make a larger effort to find a dress that works as it would be nice to look like I have more than the three things I have in my closet…Lovely model!

  24. I would go for the linen dress, and the maxi dress. You can’t beat linen for comfort on warm days. I wear dresses a lot anyway because they are cooler in warm weather. I sew a lot, so I could probably make something similar to the linen dress. I love the black dress, but I don’t have the figure for it.

  25. I love dresses… but with a toddler who still breastfeeds, they can be tricky (either I’m down on the floor playing with her and worrying about my dress riding up, or I’m nursing her and trying to figure out how the heck I do that in a dress!). Shirtdresses are my favorite because I am short and curvy, so they accentuate my shape rather than looking like a sack… and you can nurse in them. :)

  26. Hadar is completely gorgeous – she pulls all three dresses off beautifully! I think if pushed to choose I’d be torn between the first and second dresses – the linen dress is the perfect relaxed summer outfit, but that watercolour maxi is just divine. Perfect for lounging around at an alfresco dinner. Really lovely photos! x

  27. I’d love to know what kind of underwear do you wear under a jersey dress like this!
    Also, what is the model’s nail polish’s name :))) It’s gorgeous!

  28. My favourite is the linen one, but I think I would look the best in the black one!

  29. Also, I have to add- I quit wearing dresses so much when my babies are young because they are much harder to breastfeed in.

  30. I like the style of the black one, but the ease of the linen. I wear dresses and skirts a lot- a linen or cotton skirt with a tee, for example. Today I wore a short linen dress that I picked up years ago and put some short leggings under it. When I have to chase the toddler the leggings keep me modest!

  31. Susan M- I hear you! Sleeves are so hard to find! I have ordered a couple of dresses from eshakti, and they let you choose a range of options- sleeves, neckline, pockets (!), length…and there’s a good range of mod-cloth-y to classic shapes. Sometimes too quirky, but the quality seems pretty good. Lotsa coupon codes all the time.

    I love the classic lines of this black dress- definitely out of my comfort zone, but such lovely simplicity!

  32. I like all of these, the silk and the black ones especially. But I would like to find dresses with sleeves (short, 3/4 or long) with not too short a hemline, but don’t look dowdy so that I can wear them for work and non-work situations, including being out with toddler and baby. So many dress options are sleeveless, which is nice, but already creates too casual and sexy a look than I often want to have. Any suggestions?

  33. James Perse everyday all day!!

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  35. I love all three but I think the LBD is most my style!

    x Lily

  36. wow! she is so pretty. I love all 3 dresses, but I would personally LIVE in the James Perse black piece.

  37. it may seem boring, but definitely the black one! you can pair a nice scarf, or shiny belt, or the shoes you love that don’t match anything with it. so versatile, and has many more look options!

    xo Julianne

  38. em says...

    I love the first one!

  39. I want them all. I was just on Forever 21, pondering ordering all the dresses, because it’s too hot to wear pants.

  40. All three dresses look great here! I agree with another commenter who asked for more variation in body type– i’d love to see a few women with different body shapes and then have them each try on a few different dresses– or the same three dresses?– to see which looks best on each body type! Actually I am curious why you didn’t show Hadar standing in the black dress? Sitting it looks AMAZING, but it’s SO clingy… you’d have to have a very specific body to look good in it (well, either straight, or curvy but evenly proportioned). I am very thin, but a bit pear-shaped and that kind of dress looks TERRIBLE on me! PS I also love Hadar’s hair!

  41. Ahh I love the black one. So chic and simple and flattering. Buuut seeing as I’m 1. short and 2. still trying to recover my body from having a baby almost 5 years ago… I’d go with the linen. Looks so cozy and good. xx

  42. definitely the linen dress!!!

  43. Lovely model! Thank you for this. Pardon me as I purchase new dresses!

  44. I love the lines of the bodice in that maxi dress. I would feel so pretty wearing it. And, the vibrant colors! Wishlist!

  45. Haha! I feel like I dress like a 4yr old girl eg; printer legging and salt water sandals are a staple of mine. I want that black dress!!!!

  46. Looks like she’s sitting outside Buvette in the black dress. One of my favorite places ever.

  47. Hi Joanna,

    The link for the silky maxi dress doesn’t seem to be working (for me)? Could you look into that? I’d love to know where it’s from.

    Also, regarding the comments about the size of the model – I agree to some extent, but only because I KNOW how beautiful women who are larger or curvier can look in dresses, too. I have a curvier friend who wears dresses all the time and she looks amazing!

    So, I guess what I’m saying is – Jo, don’t be afraid to use plus size models or curvier girls for your photos. I’m sure your readers would love it just as much. But I do think this model pulls off all dresses beautifully and I feel like there’s a great selection going on (one for everyone..)

    Sorry for the novel :)

  48. Dress #2! I’m short so I don’t usually go for maxi dresses but I think the first one looks kind of sloppy and the last one is too snug across the midsection for me.

  49. What dresses? All I see is the city behind her. Oh and Buvette… DYING to go!

  50. The grey stripe, hands down. Your friend is super cute, as is the photo from your “past.”

  51. Linen! I love it!

  52. james perse ANYTHING is super comfy. i <3 lounging around in their tees and t-shirt dresses. thanks to thin, soft james perse cotton, my husband has finally graduated to wearing v-neck t-shirts!

  53. I think the feminine dress fits my personality/ style best. But they’re all lovely. Thanks for featuring the new line by Loft, and James Perse- both sites look like they have great collections!

  54. I love all three, but I’d probably go with the black dress. It’s more versatile, and I love wearing stand-out accessories.

  55. i see myself wearing the first dress, but the black one is amazing as well!
    xo, cheyenne

  56. I have a black jersey knit with a slighty less body-con cut that I love and wear all the time. I like the maxi through! But man, a black dress is super easy to throw on and go.

  57. Love the all of them – Hadar makes them look so amazing – much much better than the models on the respective websites:) I want to try the black one. Can you please tell me how tall is Hadar, so that I can gauge how long it will be on me?

    The best place to learn guitar –

  58. Black jersey dresses and jean jackets 4 life!

  59. I love all these dresses, but I think I’d go with #1 or #3. Only because #2 looks like I’d need to belt it in order to not look like a potato sack and I’m too lazy to find a belt :)

    She’s so beautiful and I LOVE her hair!

  60. *pockets << maxi dresses with pockets please ;)

  61. *pockets << maxi dresses with pockets please ;)

  62. I love all of those dresses but I adore her haircut the most. I’ve been growing my hair out since having a bob last year but her’s looks so effortless that it’s making me reconsider…

  63. The silk maxi is my favorite!! The colors are beautiful and more forgiving for a chubby Mama like myself! The other two are great two. Maxis are definitely my go-to this summer especially when out n about with my toddler. My only request is we need some beautiful comfy dresses with pickets!! Every mom needs a pocket!!

  64. Great post specially cause I simply loved all dresses.
    Hadar is an Israeli name, isn’t she ?

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  66. I have been wearing dresses for my entire pregnancy, and I’ve never felt prettier. Well, except for when I’m huffing and puffing to catch my breath after walking, sitting or standing. :) But seriously, I love throwing them on and only having to pick out my jewelry and sandals. As far as those dresses? I love the maxi, but would opt for the sexy black one. Old Navy has surprisingly comfortable, chic jersey dresses for MUCH MUCH less.

  67. Surprisingly (to me anyway), I have found that dresses are absolutely the easiest way to get dressed now that I’m rushing out the door to work while also trying to get a toddler and baby ready for daycare. Dress? One piece! And shoes! Done! So in a certain sense I’m dressing more formally, but it’s really just because I don’t have mental space for separates. Too. hard. So yes, dresses!

    As for these three… the first one is a little meh for me, the second would make me feel like a million, and the third looks like heaven on her but would not look like that on me. So much as I adore number 3, I think it’s got to be number 2…

  68. I’ve been wearing dresses and skirts with my trusty grey Converse Shorelines. A little bit feminine, a little bit “4-year-old” :). I love it!

  69. the black one, all day! I actually have one like that that I have been wearing a lot. it is surprisingly day friendly: belt, cardigan, and some knee high gladiators or snake print slip ons and you have a casual office look. I threw on a lacy bralet and some cool brown leather high healed sandals and it became perfectly effortless summer sexy!

  70. I am a long time dress wearer – I have always loved the airflow!

    The black one is sleek, but my gut favors the silk maxi. I would feel like a butterfly walking down the street.

  71. CC says...

    I love the second dress. But I think it might be because of the whole wanting something I can’t have. I’m short, so maxi dresses never work out in my favor. =[

  72. Loooove the first dress. But that black jersey dress is just gorgeous too!! And at 7 months pregnant it would be a dream come true to see the day I can look sexy in a little black dress again! So minus the baby bump that would be my number one choice right now if I could!! But really they’re all lovely!

  73. can we talk about the hair…? gorgeous!

  74. black dress all the way. the tomboy is cute, and i love the color and femininity of the maxi, but the black one looks so sexy, comfy, and classic.

  75. Dress 1 & 3 are definitely my style. I love to wear a fitted jersey dress to run around on a hot summer day, the colourful maxi is perfect for dinner on a patio overlooking to water.

  76. Amy P, Jockeys has the perfect under dress shorts called skimmies. They aren’t shapewear, so you aren’t constantly uncomfortable. Instead they feel like wearing a slip, but make me feel so much more comfortable wearing awesome dresses.

  77. I love the chambray dress! Gorgeous and simple. I live in dresses in the summer – not because I want to look pretty or feel girly – just because it’s only one clothing item. So really, it’s because I’m lazy :)

  78. That’s difficult. I think the third, but the second one is gorgeous as well!

  79. Oh, the black jersey for sure! That looks like a perfect wardrobe staple.

    My mom grew up in a very strict religious community where they HAD to wear skirts and dresses, and therefore only associates them with discomfort. As for me…I think pants are for the birds. Dresses all the way!

  80. I love the stripped one but I’m breastfeeding. None of these would work for me. :(

  81. I’m wearing a jersey-knit version of the linen dress right now! (And it works really well with a pair of capri leggings underneath).

    I live in dresses. :D

  82. It’s just as easy to put on a dress as it is to put on shorts and a tee, but as a mom of kids about the same age as yours I find it tough to wear one without getting my skirt flipped up! I really should find a good pair of bike shorts and then I’d feel more comfortable wearing a dress or skirt with kids. Even at a wedding the other day it was tough holding one kid and having the other grabbing my a-line just-above-the-knee skirt without getting exposed. Maybe not as sexy to wear shorts underneath, but if it gets me wearing dresses and skirts more, I think I’d say it’s worth it! :)

  83. Definitely the first one – I lean towards casual big time, and that one feels comfy but cute. Love the watercolor, but I’m probably most confident showing off my legs, so I shy away from maxi dresses!

  84. @julia1983 – this is completely why I wear dresses. Fewer things to pick out/match :)

  85. I feel like I dress like a four year old because I always wear dresses! This makes me feel better. I love dresses because you just throw it on and don’t have to plan a whole outfit. So maybe I am just lazy?! ;)

  86. is easy to wear dresses? depends, there are several circumstances under which I think is not easy:
    1. The body type, if one is chubby, buxom or if you have a lot of tummy
    2. Shaving legs mandatory

  87. As a short gal who’s also lucky enough to be short-waisted, I find maxi dresses challenging to wear. They make me feel even shorter than I really am. Any tips on how to wear a maxi when you’re a mini, would be very much appreciated.

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  89. Love them all, though none would probably flatter me all that much. I have really liked Loft’s dresses for the past few years–so much different than stuffy Ann Taylor workwear–and I think their Lou & Grey stuff is best yet. I have a perfect grey t-shirt dress from them that is rocking my summer this year. (photo here:

  90. The black dress looks great with Hadar’s tattoo.

  91. Found fabulous t-shirt dresses at Old Navy, so I’m channeling #3.

  92. Loving all three. I’m normally not a dress person but I could easily be persuaded to wear these.

  93. I love all 3 but for my body type I would probably choose #2…also because the colors are fabulous!

  94. Hi Joanna, I’m a long time reader (since before you got engaged :)), and I love your blog! I also love all the dresses here.

    However, I felt like I wanted to note that the first sentence of this post felt a little judgey, even though from what I’ve gleaned over the years, you’d be the last person to judge anyone for their choices. I just felt like the sentence sounded like if someone made the choice not to wear dresses, they weren’t as pretty and/or feminine. It just kind of struck me weird, so I wanted to share.

    Thanks for keeping such a wonderful blog. I love and read it it every day.


  95. She looks gorgeous in all of them!! The black one probably fits my personality best, but I think I would feel most comfortable in the first one. The black one would be covered in cat hair, and I’m not sure I have the body for it at the moment! Lol.

  96. I have that James Perse dress, and 8 months preggo, and it still looks sexy! I’d go for it any day!

  97. Sexy. Not to be sexy but form fitting makes me more comfortable. The first would make me look like a potato sack. I’m too short for the second.

  98. Under normal circumstances, I would choose dress 1 because it’s very much my style (as is anything chambray). Buuuuut, I’m pregnant and starting to show, so I’d have to say #3. It’s a bit more ooh-la-la than I would normally choose, but it’s no fun to have people wondering “pregnant or just chubby”? That dress would definitely send the message, “pregnant AND still sexy”!

  99. All three are very cute, and so is Hadar, but if you’re going to have someone modeling, why not someone with a less fit and slender and “perfect” body? We can already see what these dresses look like on models on the retailers’ websites…

  100. Love all 3. All my style. Unfortunately the black one is only in size 0, 1, 2, & 3!! Sigh!

  101. The first is in my comfort zone but the third is pretty sexy….I’ll take both, thanks!

  102. In love with all of them, especially the black one! But I’m trying to stop wearing so much black so perhaps I’d try a more neutral color.

  103. the first one suits my personality best, but i’d try the third one too (it looks comfy yet chic)! i’m not too into maxi dresses; i keep thinking they’ll get dirty easily.

  104. oh i love the first one! i would wear it everyday. but i must say i am intrigued by the last one…

  105. Well, they black dress is great (but I think you may need a body like hers to wear it) – they are so different (one date dress, one day dress, one kind of in between) but I love the colours of the silk one.