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12 Ways to Wear Athletic Shorts, According to Everybody From Leandra to Cat Cohen

Men’s Shorts Reign Supreme

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For those who can’t stomach wearing sweatpants once the thermostat hits 67 degrees, athletic shorts are sweats’ natural successor. I love every permutation of gym shorts: the mesh short, the track short, the basketball short, the tennis short, the bike short. And I’m not alone in my enthusiasm, based off of how quickly the Staud/New Balance shorts sold out in most sizes.

For whatever reason, unisex and mens’ athletic shorts often nail the silhouette with more consistency than womens’ do. I’ve got my eyes on some Only NY, Boast, and Tracksmith options in that genre, as well as the Everyday Shorts by Everybody.World and Petrified Goods’ take on the Patagonia baggie. Eric Emanuel’s shorts product page is like my adult equivalent of Dylan’s Candy Bar. Etsy reigns supreme as my personal favorite source of nylon soccer and collegiate mesh shorts: The site is ablaze with vintage options that combine a good, old-fashioned fit with high-quality materials and retro logos. Looking for ways to style the infamously casual gym short, I asked around and secured some recommendations from friends near and far.


Leandra Medine Cohen, founder of Man Repeller

How did you land on these shorts? I did not technically land on them as it seems like that would necessitate air travel, but I bought them last summer, about a year after Harling gently tucked them into my subconscious, with the intention of styling them for work/socializing (so not for exercise). A month later, I ended up finding these, which I actually like better, but this outfit asked for the white ones so here we are.

Walk me through your thought process of putting together this outfit: These days, I put on clothes to accommodate the desire to motivate myself to go outside (it’s not as easy as I’d have thought to push myself out the door when I’m leaving to walk aimlessly). To do this, the outfit has to be comfortable enough in the event that I’m compelled to walk really far once I’ve stepped outside, but it also must get me excited enough to get out there and parade around in, for example, a ridiculous collar, because putting on a T-shirt and leggings often won’t do it if, as mentioned, I’m doing so aimlessly. A good indicator that I have succeeded is when I want to take a picture and immortalize the outfit.

What’s the ideal location for wearing this ensemble? 89th and 5th: Hit up the reservoir (with your gym shorts) after a tango at the Guggenheim (funky collar, do you like art or something?) and breathe in the Fifth Avenue air (fancy jacket).

Catherine Cohen, comedian

Men’s Shorts Reign Supreme
Bike shorts via Amazon, Staud cardigan--another here Bike shorts via Amazon, Staud cardigan--another here

How did you land on these shorts? I needed tight li’l shorts that wouldn’t go up into my hole when I jogged! Also, as someone who was traumatized by low-rise jeans in the early 2000s, I always need the safety/nuance/elegance of a high waist. I typed “high-waisted bike shorts” into a search engine and the rest is HERstory! XO

Walk me through your thought process of putting together this outfit: I’ve been wearing this fur-collared yellow cardigan on all of my business Zoom calls to “bring the fun.” Is it working? No one knows! Also, I took an improv class (brag) in 2011 with this cool girl (had short bangs), and she wore bike shorts with everything, so this is an homage to my past… in a time when we are so uncertain of the future? That’s beautiful. Top it all off with a bejeweled headband (star on top of Xmas tree vibes), and you’re set for a day of sitting near your devices!

What’s the ideal location for wearing this ensemble? This is a great look for lounging on the couch and comparing yourself to everyone you’ve ever met via Instagram or gazing into your open fridge while picking a fight about something your boyfriend said seven months ago as he does the dishes for the fourth time in a row. The possibilities are endless!

Harling Ross, brand director at Man Repeller

How did you land on these shorts? These are the ultimate sweats-to-shorts transitional style, because they resemble and feel like sweatpants in every respect except length. Speaking of length, they happen to hit at what I would consider the sweet spot: somewhere between thigh and knee. Not too long, not too short. As Goldilocks would say: just right.

Walk me through your thought process of putting together this outfit: I wish there was a thought process to walk you through! Beyond the fact that tie-dye and stripes are two of my favorite patterns to intermix, and that I tend to prioritize comfort above all else these days, there’s not much else to report.

What’s the ideal location for wearing this ensemble? I would love to add a navy bucket hat and white Tevas over the socks and wear it to a farmer’s market.

Ziwe, Comedian

Men’s Shorts Reign Supreme
Vintage bike shorts -- similar here, Burberry top -- similar here Vintage bike shorts -- similar here, Burberry top -- similar here

How did you land on these shorts? These shorts are absolutely from high school. My athleticwear consists of free T-shirts from Walk for Hunger and whatever gear I didn’t throw away from my years running track. I got these shorts from a grizzly, bearded man named Blaine, who ran my high school’s equipment room.

Walk me through your thought process of putting together this outfit: The thought process behind this outfit is, “How do I trick myself into caring about anything?” Doing my makeup and turning looks are the only things that energize me during quarantine.

What’s the ideal location for wearing this ensemble? The ideal place to wear this ensemble is hiking through the Spanish countryside with my future husband, Raul (name + region subject to change!).

Ansley Morgan, stylist

How did you land on these shorts? I came back to Georgia for my birthday in March and never left. I only packed for four days. As a result, I have become reacquainted with my college wardrobe, which consisted of oversized T-shirts and Nike shorts—the uniform for southern sorority girls. I sold a lot of my Nike shorts before I moved, but held on to the most unique and fun ones. I kept this orange and pink pair for obvious reasons.

Walk me through your thought process of putting together this outfit: When I make the decision to wear something as bold as these shorts, I decide to commit to that color palette. This Nikki Chasin top, which I’m very thankful I packed, fit the bill. It is cool and comfortable, making it appropriate for spring and summer. I wanted to style the shorts in a fun way that also elevated them. So I threw on my necklaces from Brinker & Eliza and Hey Harper. The final touch were these shoes from Labucq that I can’t wait to wear on the streets of New York when I finally return.

What’s the ideal location for wearing this ensemble? I would wear this outfit to lay about in the park with my friends. We would all be safely distanced and dining on our own personal wine and cheese pairing.

Tiffany Wilkinson, creative director at Man Repeller

How did you land on these shorts? The past four summers, I’ve been a faithful Patagonia Baggies devotee. They are the perfect short to take you through a summer’s day, whether hiking, biking, jogging, swimming, or just trying to stay cool on the subway platform when it’s 100 degrees. They pack well and dry quickly. You can fit a tennis ball in the pocket, and the five-inch inseam offers a good amount of thigh coverage, without looking too frumpy.

Walk me through your thought process of putting together this outfit: Memorial Day is around the corner and like most folks, I’m going nowhere! As the adage goes: “Dress for the vacation you want, rather than the vacation you have.” So here I am ready for the beach. No travel, no problem!

What’s the ideal location for wearing this ensemble? This outfit’s spiritual home is Jamaica, a place I’ve never been to but would love to visit one day. Seeing as a trip to the Caribbean is off the table for the foreseeable future, I’ll be wearing this outfit to brighten up my regular walk through Greenwich Village to the Hudson River and back to my apartment in Alphabet City.

Naomi Elizée, Associate Market Editor at Vogue and Podcast Host

How did you land on these shorts? They’re from Outdoor Voices! OV is my go-to athletic brand, and I have these bike shorts in every color.

Walk me through your thought process of putting together this outfit: It’s all about comfort for me these days. I have an action-packed day full of Zoom meetings, so I wanted to remain comfortable but still be stylish. I opted for my beloved Chopova Lowena top so I can give the illusion on Zoom that I am more dressed up than I actually am! I paired the top with my OV bike shorts and these incredibly comfortable slippers from Nomasei. I added the sunglasses for a bit of flair for when I work out of the backyard this afternoon.

What’s the ideal location for wearing this ensemble? From my couch to the kitchen to the backyard! This is the ultimate WFH fit.

Elizabeth Tamkin, market strategist at Man Repeller

How did you land on these shorts? I saw someone wearing them on Instagram’s Explore page—which I frequently visit these days—at the very start of quarantine. I love that they’re sweatpants material, flare out a little bit, and, because they’re mens, a bit oversized. Oh, and the pockets are fantastic for hiding dog treats to distract my dog while I’m working,

Walk me through your thought process of putting together this outfit: I usually wear these shorts with just a tank top or cami and a bunch of necklaces (must look presentable on my video calls!). Here I am wearing a cream-colored fisherman sweater over the cami. I find myself dressing monochromatically a lot these days. So from start to finish: I pulled out the shorts from the pile of clothes I wear the most, put on my favorite ribbed tank, got chilly so added a sweater, and put on shoes that I actually just wear around my apartment these days (yes, their soles are clean!).

What’s the ideal location for wearing this ensemble? The Man Repeller office, which is where I wish I were. Or sitting cool and comfortable at brunch with friends… or more realistically with my quarantine partner—formally known as Man Repeller’s Friday Happy Hour bartender—on the couch with a giant bowl of cereal (light on the milk please!)

Iman Hariri-Kia, Sex & Relationships Editor at Bustle and MR contributor

Men’s Shorts Reign Supreme
Nike shorts, Dickies T-shirt, vintage blazer—similar here Nike shorts, Dickies T-shirt, vintage blazer—similar here

How did you land on these shorts? These Nike basketball shorts were stolen straight out of my partner’s closet. I stumbled upon them when I was looking to steal a pair of his fun, patterned swim trunks, but I couldn’t find them, and thus, settled for these bad boys instead. (Plus, I don’t think he “balls” that often.) I love the navy, white, and gray color combo, and the fit reminds me of my high school P.E. shorts, pre-rolled, which I’ll admit I never thought I’d be nostalgic for. But alas, here we are!

Walk me through your thought process of putting together this outfit: Well, I started with the shorts, which are sort of hilariously long and oversized, so I knew from the get-go that I wanted to play with proportion. My white Dickies T-shirt is perfectly cropped, but this vintage lightweight blazer is similar in dimension and scale to the shorts. In some ways, they feel like a set, even though they’re complete opposites. The concept makes me giggle—the idea that I could break into a brisk jog or a power walk on my way to a business luncheon. If I had literally anywhere to go, I’d pair this with a naked heel from Staud. Instead, I’m wearing white ankle socks. Still chic, no?

What’s the ideal location for wearing this ensemble? I’d wear this to a breakfast meeting with an old co-worker, who started at the company as an assistant. We made our way up the ranks together, but he made a surprise departure from the business. Mid-way through deviled eggs and whipped buttermilk pancakes, he tells me he’s starting his own firm and taking half my clients. I’m devastated! I take my cold brew and splash it right in his face, blam! But then, the big reveal: I had him tailed and knew what he was planning. And I’m suing him for breaking his non-compete. He confesses that he’s in love with me, and we passionately embrace. Then I tell him that I still intend to take him for all he’s worth, before strutting out of the restaurant, still sipping on the remainder of my coffee and leaving him with the check.

Also, in this scenario, I am Samantha Jones.

Lauren Chan, founder and CEO, Henning

Men’s Shorts Reign Supreme
Vintage shorts--similar here, Roots sweatshirt Vintage shorts--similar here, Roots sweatshirt

How did you land on these shorts? In a former life, I was a basketball player. These are the team shorts from when I played on Team Ontario as a teenager.

Walk me through your thought process of putting together this outfit: Since the shorts are super Canadian, I grabbed the most Canadian top I could find: a vintage Roots sweater. Everything I’m wearing these days is comforting, and above all else, easy. No styling, all ease.

What’s the ideal location for wearing this ensemble? Am I socially allowed to say anywhere beyond my apartment?

Zoe Schlacter, textile designer and artist

How did you land on these shorts? I picked out these athletic shorts because I like that they are masculine-looking while still fitting well. Wearing them right now because they have an elastic waistband.

Walk me through your thought process of putting together this outfit: This top by my friend Tyler McGillivary is my current favorite garment—I’ve been wearing it a ton lately. It’s pretty silky and glam, and I love how it looks with something casual on the bottom. I’m wearing the boots because they make me feel tough!

What’s the ideal location for wearing this ensemble? For a walk around the block with my partner and their dog!

Hannah Mosman, apparel designer & stylist

How did you land on these shorts? I love these shorts because they’re made from a super comfy tricot knit and have piping down the front. They also remind me of Armie Hammer’s shorts in Call Me By Your Name.

Walk me through your thought process of putting together this outfit: I enjoy looking to athletic styling from the 1980s and ’90s, when workout pieces were less “technical” and more casual, and often paired with denim, button-downs, or other non-athletic apparel. Taking that direction in combination with any excuse to dress like Leo DiCaprio in Romeo + Juliet, I paired it with my favorite tropical-print camp-collar shirt belonging to my partner. I live in this cotton Calvin Klein sports bra already, but it also felt like a key inclusion. Tube socks and neck chain followed suit as parts of a natural ’80s progression.

What’s the ideal location for wearing this ensemble? Ideally, I would wear this ensemble with a tan while exploring Old San Juan, Puerto Rico.

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