Sometimes, I’m all about a dress. Zipping one on before a wedding or holiday dinner or special event feels right. Sometimes, I don’t mind feeling done up, all womanly and put together, like the grown-ups I admired as a kid. But day-to-day, I prefer to feel casual and boyish. This presents a challenge in the summer, when structured layers feel like wet blankets and frilly dresses like a breeze.

Dresses are girly. They often convey a spirit that, while perfectly okay, doesn’t really feel like me. And they do it in one fell swoop. I get that the one-and-done nature of dresses is part of the appeal, but to me it feels constricting. A full outfit, on the other hand, is easier to manipulate and make my own. A slinky tank can be pared back with old Levi’s and high-top Converse; an A-line skirt by a baggy vintage tee; tight-fitting pants by an oversize denim jacket and a baseball hat. But those are just too hot in the summer. My knees and elbows need to breathe. Heavily. And shorts are just hard.

How do I make a dress feel dressed down? How do I wear a dress without feeling like a summer daisy, even though I love summer daisies platonically? When I posed these questions the other day, Leandra jumped in right away. “You can totally wear a dress and still look cool. Let me style you for a story!” I obviously obliged. Have never done so quicker, in fact. And I’m so glad I did, if for no other reason than having the honor of wandering around a sculpture garden in four-inch heels, feeling like Leandra’s well-loved Barbie doll.

Scroll down for the fruits of her labor. Three dresses, three outfits, nary a flirt, if I have a say in it.

1. A strawberry in tube socks

When I saw this dress on the rack, I must admit I was horrified. It’s so feminine. Look at the ruffles! That shape! So pretty and so not me. I imagined she’d style me in structural, cotton dresses, perhaps tea-length. This felt like the opposite of that. But a pair of tube socks and sneakers later, I started to understand her vision. She’d somehow managed to make this strawberry dress feel less sweet, more cool. A fete unto itself.

Consensus: Would I wear this dress? Probably not. But! I didn’t feel silly in it at all, and I definitely plan to co-opt this look thigh-down. Sneakers with a dress changes the whole thing.

2. Cleopatra if she time-traveled to the ’90s

I’ll be honest: When I put on this silk dress, I got a pit in my stomach. This time I did feel silly, like a fraudulent Cinderella. It was hugging me in places I don’t prefer to be hugged and I struggled to hide the discomfort on my face.

“What’s wrong?” Leandra asked me.

“I don’t know,” I responded, my cheeks flushed red, “I would just never wear this.” It would look so much better on her, said an evil voice in my head. I wanted to hide. But then she grabbed a flannel and knotted it around my waist, disguising the dress, and dropped a bunch of necklaces over my head, transforming the neckline, and I felt the whole thing change. I was beginning to understand that dresses don’t have to be one-and-done.

Consensus: Wearing this casually — like to lunch — would make me feel like a wannabe Leandra, rather than myself, but I’m 100% taking these style cues for next time I genuinely need to dress up. I’ve never looked this cool at a formal event.

3. A cool teen who lunches

This dress, which is short, ruched and covered in pink and purple flowers, isn’t something I’d even pause on while shopping, much less buy and wear. But wear it I did, with bright pink heels no less. I was thrilled to add the flannel though, it felt like home. As did the bandana; I wear neck scarves a lot. This outfit probably felt the most like me, but it’s also the least wearable on a hot day, which might boot me back to square one.

Consensus: Oversize button-downs can dial anything back. A lighter one might work on not-too-hot days. I might even be able to pull off something this feminine and still look casual, if I can just find the right attitude. (Still working on that.)

My main takeaway from this experiment is that I’m not thinking creatively enough when I style dresses. Adding doesn’t have to mean adding hot layers, it can mean adding something super unexpected (like tube socks) or disrupting the shape (with another shirt) or further deviating from the rules. Less coverage doesn’t have to mean less interesting. I’m excited to head into summer with that attitude.

Photos by Edith Young, styled by Leandra Medine.

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  • Rhianne Barreto

    THE STRAWBERRY LOOK !!!!! YOU LOOK INCREDIBLE !! dude I wanna dress like a different fruit every day of the week…is that a story I do not know???

    • Kaylan Waterman

      fruit dressing! let’s make it a thing!

      • Haley Nahman

        Make this a thing please and thanks!!

  • Aydan

    Its so true! dresses easy can be dressed down when you include more casual shoes on the bottom!! and if you wear a tank dress, wear a tight short sleeve crop top underneath (if you can manage the extra layer) giving it more of a casual look! I’m all about being somewhere in the middle of super feminine and masculine and find that switching up footwear and changing what goes under over really does make all the difference with a dress!

    • Haley Nahman

      good tips thank you!

  • Cynthia Schoonover

    I really like the strawberry dress! I frequently wear dresses to work, and I change things up with shoes, tights, scarves, cardigans, or jackets. Depending on shoes and accessories, I can dress up or dress down a dress. Nothing beats a dress for comfort in hot weather.

    • Haley Nahman

      I RECLUCTANTLY agree

  • Bree

    Hayley you’re a bloody babe!

    • Haley Nahman

      :O ty! but also literally bloody because i had my period during this shoot tbh

  • Cristina

    The link for the sunglasses is the third pic is empty, does this mean they sold out because those are mayj and I would be sad!

    • Haley Nahman

      I think eliz fixed!

  • Ariel

    Haley! I love you in these dresses!!! Especially the strawberry one:)

    • Haley Nahman

      THANKS ARIEL

  • Andrea Raymer

    I have been starting at a photo of dress #1 in Pinterest for about a month because that dress is all I want to be this summer.

    • Alicia Celeste

      I just bought that dress! it really is great… i’m a size 6 and I bought Medium. The material is a bit thinner than I thought, but it’s actually great for summer! my shoulders and arms get burned easily so it works out :).

  • Kaylan Waterman

    Your calmly reluctant face that is also somehow a smirk is giving my lyyyyfe hahaha. I think you guys made an unsuspectingly great team.
    Also, this was super helpful! I like dresses, when they can be comfortable, but am not great at dressing them down and convincing everyone (and myself) that putting on a dress doesn’t mean I’m dressing “up.” well done, yo!

    • Haley Nahman

      SAME! we’re the same

  • Leandra Medine

    so proud of myself

    • stinevincent

      Y’all should do a follow-up where Haley strikes out on her own with a few dresses.

      • Lilli

        I second a follow up! Haley you look awesome in all of these outfits, I would love to see your spin on it!

        • Haley Nahman

          I am game!

  • Riley W

    I love dresses so much. I own 2 pairs of pants and one of those is leggings. These dresses are all great. Wow.

    • Haley Nahman

      WHAT!

      • Riley W

        My legs just want freedom!

    • same!! but i’ve not been out of my new pair of jeans, #2 in my current wardrobe, for like three months.
      (do you want me to write a jeans version of this?: http://www.manrepeller.com/2015/01/how-to-style-a-turtleneck.html)

      • Lindsey

        jeans4lyfe

    • BarbieBush

      omg my friend owned NO PANTs. She just didn’t have any. We went horseback riding and it was a more difficult time for her than most.

      • Riley W

        Oh I guess I’d probably break out my one pair of jeans? Can you wear leggings horseback riding? I’ve never delt with this conundrum.

  • Filatova Anna

    love the second look!

  • Zoe

    your hair looks so cute with that black headband!

  • Sheila T.

    I have the first dress in a summer daisy print (SO LITERAL) and I love it but now I have even MORE inspiration so THANK YOU for helping my limbs breathe this summer!!!!!!!

    • Haley Nahman

      lol @ summer daisy dress & I will pass your thanks onto leandra!

  • Caro A

    you’re a true beaut!

    • Haley Nahman

      :*

  • Harling Ross

    Would date u.

    • Haley Nahman

      would marry u

      • Lauren Holt

        Would be best friends with both of you ? Yes. Not a question. <3

  • Helen

    As a year round jean(s?) wearer this is inspiring. Looking forward to a lack of leg sweat!

  • Adrianna

    Lately I’ve been trying to figure out dresses in my late 20s. I feel silly and juvenile in the “girly” dresses I wore in my early 20s. I have an hourglass body and a large bust, so a lot dresses either look va-va-voom or precious.

  • BarbieBush

    omg you look awesome in dresses. *Not creepy* there is this insta photo of you in a dress with a cat and glasses (maybe its a skirt) and when i saw it i was like omg has anyone looked more chic ever..

    • Haley Nahman

      Oh yeah that’s a skirt!! Good mem!!

  • Lindsey

    I definitely needed this article! I have dresses purely because I live in LA and I CANNOT abide being hot. And shorts are so uncomfortable; I’m always pulling them back down from where they’ve crawled up. But like Haley, I have a much more boyish style. I’m not into pink, ruffles, or anything resembling “flirty”. Reformation dresses are about as girly as I can get, but I still will never cross over into their gingham dresses. I just can’t. But this is helpful! Yes, dresses *can* be one-and-done, but it doesn’t have to be. I think look 2 especially showed me the power of accessories. And I have been doing the sneakers with dresses things (or oxfords) for a bit. It makes me feel more like myself.

    • Haley Nahman

      i’m def into the sneaker move too

  • nessa teran

    you look incredibly cool in outfit number 2. you should wear it every.single.day.

    • Haley Nahman

      i would look CRAZY!

    • Rachel Dlugatch

      outfit no2 is my fave by far!

  • Bo

    Haley, You excel in purple

    • Haley Nahman

      never thought i’d hear the words

  • Kay Nguyen

    The 2nd look is definitely more my taste! Thanks for trying these out so I don’t have to <3

    https://www.myblackcloset.com/

    • Haley Nahman

      :*

  • Athena Politou

    I love the first outfit so much omg

  • Natty

    omg haley, that second look on you is INCREDIBLE! you do not at all look like a “wanna-be”– you just look awesome and confident and cool. GIVE US MORE

    • Haley Nahman

      omg THANK YOU!

  • Julia Reiss

    I own that Réalisation Par dress and it’s fab, but I was wondering if you wore a slip under it or something, because it’s very transparent. #SlipSOS

    • Haley Nahman

      I didn’t! But def had to put on nude underwear

  • pallavi singh

    How about just an oversized button down as a dress or maybe a linen shirt dress? The j-crew sleeve roll, with combat boots/ hi-top sneakers and a neck scarf would look great!!

  • Very sweet girl clothes are great.http://www.elektroniksigara.us.com/

  • Sun Anni

    So, the 2nd look is you, in Seattle, a member of the Bangles back in the day (love it!).

  • Rheanonn Perez

    it’s unanimous, the second look is SO GOOD!

    frheak.net

  • chouette

    The shades in look 2 are DEF a keeper, they’re so flattering with your hair!

  • Baby, like this is perfection

  • Dafne López Toigo

    Can you please do a “5 ways to wear sport clothes if you hate sport clothes”?

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  • very sweet and beautiful style Paykasa I really liked you very much like an angel