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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