S

omething I really like about summer is how the weather provides an occasion to really get dressed where there might not ordinarily be one. Despite temperatures and humidity levels that might reasonably demand basic, sweat-wicking materials, it seems like people really take advantage of the vacation-like energy that appears magically in June. Maybe we’re nostalgic for the time in our lives when summer meant no school, no homework, no obligations. Maybe we’re just that sick of utilitarian coats. Either way, at least around New York, summer seems to have a way of encouraging us to add an extra earring or try out silhouette we normally wouldn’t. It provides an excuse to wear only swimsuits or break out the thing we’ve been saving, because if not when the sun is shining, then when? As a result, even in the least amount of clothes, everyone appears so much more fully dressed in June, July and August. And it’s so much fun to look at.

Because I can’t get enough, I asked 10 women to show me their Summer Looks, capital S, capital L — the outfit they keep wearing over and over because it so perfectly captures who they right now — plus what inspired them, how they feel in them and, for very important context, their go-to summer drinks.


1. Leandra Medine

Founder, Man Repeller

If you had to give this outfit a high school superlative, what would it be?

Most Likely To Be Worn on the Way Home From a Long-Winded Meditation Retreat So As to Demonstrate Without Having to Say Every Twenty Minutes That You Are Now an Enlightened Individual.

Why is this your Summer Look?

This dress isn’t necessarily my summer look so much as the color (or lack thereof) palette is. I find that I’ve been gravitating towards combinations of white and ivory in whatever form they want to take. The majority of the time, they’re cotton shorts and linen button-down shirts, but sometimes they’re dresses or drop-crotch pants or T-shirts. My guess is that I am after simplicity — a lack of complexity in what I wear that does not suggest I am “simple,” but rather, it highlights the multidimensionality of being human. Whoa, I stopped thinking for a second and just let my fingertips type, tbd on whether that actually makes sense but we are going to go with it for now.

Where did the inspiration for this summer look come from?

Nazareth.

How does it make you feel?

Put-together — like I showered this morning, even though I haven’t showered since last week. Like I have time to stop and smell the roses. Like the luxury of ordering coffee “to stay” is one I take for granted because I am afforded its stillness so regularly.

What’s your go-to summer drink?

Oat milk over ice. I feel like I was sleeping when Oatly blew up, so I’m doing my part to make up for the time I missed.


2. Diana Tsui

Pleats Please Issey Miyake top — similar here, Tibi culottes, Celine mules

Senior Market Editor at The Cut, @chupsterette

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Be Mistaken for the Art Teacher, or Most Likely to Be Twinning With My Art Teacher.

Why is this your Summer Look?

I HATE summer about as much as I hate wearing color, which is to say: a lot. I can’t imagine myself in bright floral prints, off-the-shoulder tops or any other warm-weather trends — it doesn’t really suit my personality or style. Instead, I’ve figured out that I like a uniform year round. It always centers around something avant-garde looking, usually by a Japanese brand. If it’s a top, I’ll wear it over jeans or trousers, and if I’m in a crazy skirt, I’ll tuck in a camisole or sleeveless turtleneck. And no matter what, I always choose comfortable shoes.

This outfit ticks all of the boxes since the Pleats Please top feels like something an extremely hip Tokyo grandma would own in triplicate. The Tibi culottes are a really old pair of pants that have held up well and have enough volume to strike a balance with the tank. I would normally wear flats, but I had to run around today to a few appointments, so I swapped in these low-heeled Céline mules that play off the black-and-white palette.

If I weren’t in this, I’d most likely wear a (probably black) Comme des Garçons skirt with pleats or crazy ruffles, coupled with a camisole and Nikes or sandals. It’s mindless but still looks like I put in effort.

Where did the inspiration for this summer look come from?

Winter is my favorite time of year since I love a good turtleneck, snowboarding and feeling perfectly climate-controlled. Come summer, my only goal is to wear the least amount of clothing against my body without feeling like I’m over-exposed. Also, I really hate anything that clings to my figure — it only serves to add to the sweat levels! So I’m always trying to figure out how to do that and still look like I work in fashion. I’ve discovered that choosing stuff on the fringes of whatever is currently trendy helps me do that and also keeps my budget in check. I can rewear this over the next three years and it won’t look outdated, which makes it worth the price tag.

I always joke that I want to become Rei Kawakubo, especially as I get older. I really hope this is a step closer in that direction. She’s so damn cool.

How does it make you feel?

Like I can survive the next two months? I just need it to be snowy and dark!

What’s your go-to summer drink?

Iced coffee with oat milk during the day unless I’m being super fancy and indulgent, and then it’s a milk tea with grass jelly, pudding AND boba. If it’s nighttime, then all I want is an orange wine that’s super funky and turns off most people around me.


3. Jenny Walton

Illustrator, @Jennymwalton

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Get Detention for Showing Too Much Stomach.

Why is this your Summer Look?

It’s my summer look because it’s so comfortable, but it still feels fun.

Where did the inspiration for this summer look come from?

From wanting to combine all of my most comfortable pieces and then style them in a way that still felt fun and not boring. To do that, I knotted the top and added a fun statement earring and a cute bag to match the striped shirt.

How does it make you feel?

Like I could go from the beach to a party! (Even if I’m just going from walking my dog to picking up a salad.)

What’s your go-to summer drink?

I think I overdid it on Campari last summer, so now I’m onto the Cappelletti Spritz instead. But I’ll still have a plain Campari soda every once in awhile. It’s so simple that it’s hard to beat.


4. Minami Gessel

white top jeans nike sneakers woman

Glossier Editor, @minamigessel

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Make Her Own Almond Milk.

Why is this your Summer Look?

The sleeves are linen, so it’s breezy and keeps me cool. Sneakers, because comfort.

Where did the inspiration for this summer look come from?

German milkmaid discovers comfortable sneakers that make her look taller than she actually is.

How does it make you feel?

It makes me feel cute and sexy.

What’s your go-to summer drink?

Shake Shack’s watermelon basil lemonade with a dash of Sprite! Hella fresh.


5. Abisola Omole

CEO & Creative Director of The Apārtment Global Group (arva, The Apārtment & Fole Studio)

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Be Underestimated.

Why is this your Summer Look?

It’s comfortable, and I think it’s also quite casual, but I guess due to the color palette and accessories, it can also be worn in pretty formal environments too, making it perfect for most occasions, which is great because most of my days take random turns.

Where did the inspiration for this summer look come from?

I recently spent lot of time in Majorca, Spain, and everything from the overly relaxed way of life, which encourages neutrals and comfort, to the sunny weather, which inspires light and soft fabrics, to the fun and entertaining side of the culture, which probably led me to explore wearing more jewellery than I typically do, has made me gravitate towards pieces that represent how my time there made me feel.

How does it make you feel?

I know I keep saying comfortable, but it really does make me feel comfortable! But alongside the comfort and practicality, it makes me feel mature, confident and ready for wherever my day takes me. Plus, with the jewelry, I feel quite fancy — probably because I never wear this much!

What’s your go-to summer drink?

Aperol spritz slushie!


6. Claire Beermann

Editor at ZEITmagazin and founder of C’est Clairette

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Get Denied Access to an Italian Cathedral.

Why is this your Summer Look?

This summer has been the most incredible I’ve ever experienced in Berlin – we’ve basically had sun and heat for three months straight. I’ve been in a swimsuit the whole time because sweating doesn’t feel gross in it. Plus, you’re always ready to join a pool party or dip into a fountain. The dress I found in a lovely vintage boutique during a work trip to Florence is the result of my newly developed passion for Italian style — you know, the beautiful patterns, the feminine dresses, the fun-loving atmosphere around it. There’s something equally effortless and over-the-top about the way Italian women dress. I’ve worn this outfit during aperitivo hour on my balcony and buttoned it up to go outside (society here in Europe requires me to do so).

Where did the inspiration for this summer look come from?

I think it came from a fantasy. I’ve been picturing myself lounging in an olive garden in Puglia all summer, probably because I’m actually (finally!) going there in September (after seemingly everyone has been on vacation except me). And if a swimsuit paired with a Missoni dress and hoop earrings isn’t the perfect outfit for this kind of setting, I really don’t know what is.

How does it make you feel?

It makes me feel so free! Not only because it’s basically just a swimsuit and a shirt and takes me five seconds to put on, but also because it offers a way to let my thighs breathe without having to put them in shorts or denim cut-offs (which I love on everyone except me).

What’s your go-to summer drink?

Daytime: homemade ice tea (made from Earl Grey, lime juice and a few drops of maple syrup). Evening: Campari orange, always and forever.


7. Preetma Singh

Managing Fashion Editor at Nordstrom, @preetmasingh

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Make a Comeback.

Why is this your Summer Look?

I’ve been on a mission to streamline my life this summer, and my closet has been a big focus of that. I wanted to stop thinking, “I should keep that in CASE” … I wanted my closet to be things I could pull together almost at random that could work for the majority of places I go on the regular. Basically, I wanted to front load the effort so I can be lazy about dressing but still look polished enough. A denim pencil skirt and polo with a low-heeled sandal and crossbody bag is that boiled down to its essence: kind of casual, kind of dressy, kind of classic, kind of trendy, very easy. Looking for classic pieces with unique details is an easy hack to get there.

Where did the inspiration for this summer look come from?

This is how I dressed in high school! I loved denim pencil skirts, I loved polos, I loved a thong sandal — and I still do! There are some pieces that are part of your style DNA and I feel like I’m (re)discovering those in the great closet purge of 2018. Some things you just always feel good in.

How does it make you feel?

Good! But seriously, I feel like I don’t have to fuss or worry about something being out of place, which is paramount. I get really fidgety and anxious otherwise. The Sagittarius rising in me also feels like I could be spontaneous in it — like I could go to a nice dinner on a whim or to the beach…or just to work, which is most often the case.

What’s your go-to summer drink?

Rachel’s Ginger Beer in Seattle makes delicious coconut dark ‘n’ stormy slushy drinks. They are dangerously yummy and strong.


8. Elizabeth Giardina

Caftan made from Kenyan Kanga cloth via Etsy — another here, Proenza Schouler leopard slip-on shoes, Love Adorned silver bangles, two gold Persian necklaces from my husband’s grandmother

VP Design, Proenza Schouler, @elizabethgiardina

If you had to give this outfit a high school superlative, what would it be?

Most Obviously Knocked Up.

Why is this your Summer Look?

Because I am pregnant and I seem to feel the happiest in a bikini or a caftan.

Where did the inspiration for this summer look come from?

Necessity. And I don’t like maternity clothing. Also I love the colors of this Kanga cloth.

How does it make you feel?

Like I am channeling my inner earth mother.

What’s your go-to summer drink?

Club soda with bitters and lime. Damn I miss a stiff drink.


9. Ellie Nesmon

Digital Talent (Instagram), @slipintostyle 

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Be ET’s Date at the Leopard-Themed Senior Prom.

Why is this your Summer Look?

It’s my summer look because it’s super easy to get in and out of and I can wear multiple versions of it with different tees and different wrap skirts every single day and no one one will ever notice, I promise.

Where did the inspiration for this summer look come from?

During summer, it’s too hot to wear long sleeves, but at the same time, I need to protect at least one part of my body — my legs in this case — from mosquito bites, so a T-shirt and a midi skirt sounds like a good compromise.

How does it make you feel?

It makes me feel all sorts of ways: glamorous because the skirt is silk, cool because I’m wearing a “Space Cowboy” T-shirt and a bit like a modern-day Marie Antoinette because of the big velvet bows on my silver mules.

What’s your go-to summer drink?

A creamy and thick piña colada with a pink umbrella and pink sugar on the edge. It’s the only way to make me feel like I’m really on summer vacation.


10. Miski Muse

Ralph Lauren top, Levi’s jeans, Nike shoes, vintage hijab from What Goes Around Comes Around — similar here, Gap straw bag

Model and Student, @musegold

If you had to give this outfit a high school superlative, what would it be?

Most Likely to Ruin My White Top by Lunchtime! (I love white but am terrible at keeping them clean.)

Why is this your Summer Look?

My summer look will always be a tee-and-mom-jeans combo. A silk scarf material keeps me cool in the summer. The straw tote has been a staple this summer — my favorite trend of the year! As for my shoes, sneakers are always in and comfortable for a long day of meetings and running around the city.

Where did the inspiration for this summer look come from?

Comfort! I’m inspired by things that make me comfortable and are versatile. I like wearing something that I can dress up or dress down depending on what I’m up to that day.

How does it make you feel?

Beautiful! You always feel good when you find jeans that fit, right?! Pants that fit me in all the right places can make me feel like I’m on the moon.

What’s your go-to summer drink?

I make a mango smoothie every morning! I love smoothies because they reminds me of summer and they’re refreshing. I’m also an iced coffee addict and proud. French vanilla or caramel are always a good idea.

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