Conquering Shorts: Our 5 Favorite Styles

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With summer just around the river bend, three things are on the rise: overall wellbeing, iced-coffee consumption and shorts anxiety. I’m of the view that the first is biological, the second is reasonable and the third is, with a little effort, capable of being quashed forever. I’m on that journey myself.

Somewhere along the narrative arc of my personal style, I decided I was more of a pants person. The exact reasoning is a murky mixture of legitimate style (I love a long swath of fabric), my own insecurity (I’m more comfortable with my legs covered) and a simple lack of experience (San Francisco’s climate never demanded shorts). When I moved to New York and came cheek-to-cheek with muggy summer days, I was thrown. My pants didn’t work because I’m not a masochist, I only had a few dresses to my name and none of my shorts made me feel good or like myself. Whenever I asked people how they got dressed in the heat, I was mostly met with groans. Shorts, in particular, seemed to solicit a lot of ughs.

Shorts can be tough because, in their most classic iterations (short, tight), they’re not so forgiving nor poised, in terms of surface area, to pack much of a punch. But I’m slowly learning that the trick to beating shorts anxiety is to find the one style that makes you feel like a fr34k on a leash in a good way and then buy a few and wear them until they fall off your body. That might mean daring to deviate from the seemingly ubiquitous denim cut-off or it might mean really committing to them — Shari calls them “coochie cutters.” I asked her and three other women at MR who seem to be at one with their shorts to talk me through their favorite pair. I, too, donned my new shorts of choice — although I’m still exploring.

Take a scroll to see what we said and then tell me a) if you have shorts anxiety and b) about your go-to pair, if you have one. Maybe we can lean on each other to get through this hot-summer weather. Shorts don’t have to be scary.

I like my shorts high-waist, voluminous and bloomer-like (but not soft!)

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3.1 Philip Lim shorts, Maryam Nassir Zadeh shoes, vintage polo, street vendor sunglasses

“I discovered these babies by way of classy woman named Harling Ross. I call them Modern Jane Goodalls. Since I pretty much only wear pants with a high waist, I don’t know why I’d deviate from that in the summer. The material needs to be stiff and have a bit of structure. The thought of flowy or silky shorts makes me want to climb a tree and not come down. I enjoy that the leg openings give my thighs room to breathe, which makes me more physically and emotionally comfortable. If I’m being honest, the shoes and shirt aren’t totally working for me here, but I’m still finding my way when it comes to styling shorts. I’ll get there.” — Haley a.k.a. me

Leandra likes her shorts with a reverse A-line — shorter on the sides, longer in the crotch

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10 Crosby Derek Lam shorts, Miu Miu sweater, Amelie Pichard shoes

“I don’t have shorts anxiety. If anything, shorts feel more comfortable to me than pants (we all have our stuff). I have this exact pair in two color variations — this one, which I wore for the majority of last summer, and another I found at Nordstrom Rack a couple of months ago in utility green. The leg holes are wide, so they make walking and sitting, etc, really comfortable. They’re not super-tight, so I don’t feel ‘exposed’ when I wear heels, and are forgiving enough that I don’t have to think about what I am or am not eating when I wear them. That’s a shitty thing to say, but getting dressed is so interesting in that it can trap you (pretty literally) or set you free. And as long as you know what it feels like to be ‘set free’ in your clothes (different for everyone), you’re set up to feel good more often than you’re not.” — Leandra

Erica likes her shorts fitted, stretchy and high-waist

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American Apparel shorts — similar here, Junk Food Michael Jackson T-shirt, American Apparel shirt — another here, Urban Outfitters shoes

“I have to admit that I don’t really relate to shorts anxiety. I like to show leg more than anything else, so shorts are essentially my going-out tops. I like this black, high-waist pair because it’s really easy to make them look nighttimey. I’ll wear them with something looser, like a graphic tee (to balance out the tight fit and butt cheek-skimming length), then throw on loud sandals or heels. If I’m out in public while the sun is still up, I’ll bring along this sheer thingie. The sleeves add some faux-modesty, but it’s still completely see-through; seamless day-to-night transition if you ask me.” — Erica

Harling likes her shorts high-waist, structured, mid-thigh and trouser-style

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Toteme shorts, Isabel Marant Etoile dress, Chanel jacket, Roxanne Assoulin earrings, Preen by Thornton Bregazzi sunglasses, Oscar de la Renta slippers

“I only have shorts anxiety vis-a-vis denim cutoffs. I’ve never found a pair that feels ‘me,’ though there have been various periods of my life during which I tried very hard. Maybe I should give up, but I think I have a women’s magazine demon on my shoulder whispering summer staple summer staple summer staple. This shape is my favorite because I feel like a fun businessman when I wear them. I also find them to be the most flattering AND — this is very important — comfortable. I hate the feeling of shorts digging into me when I sit down. I just can’t do it.” — Harling

Shari likes her shorts denim, cut-off and “coochie-cutting”

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Vintage Levi’s shorts, J.Crew T-shirt, Zara shirt, Gap clogs — similar here

“My legs are my favorite part of my body, so I’m always happy to show them. These are my favorite because of their ease and versatility. I usually dress them up with pumps or a heeled sandal and then add a looser top. I dress them down with sneakers and a crop top on a nice relaxed day. They also just make me feel very cool, because I can get them as dirty as I want and they still have this edge to them. They’re like Converse sneakers, the dirtier the better!” — Shari

Photos by Edith Young.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

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