Conquering Shorts: Our 5 Favorite Styles

Shorts don’t have to be scary

Abate Shorts Anxiety May 2017 Man Repeller1.0 (4 of 7)

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.

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  • Julia

    Glad you posted this because quite literally 45 minutes ago I was having shorts anxiety as I got ready today. I prefer them to be loose but short and high waisted for sure because they always ride up anyways. I ended up in denim ones from madewell that are def not my fav and I like to wear a long shirt to cover my butt in them but they were all I could muster as I didn’t have a shirt to match my favorite pair. It was a struggle for sure.

  • Rheanonn Perez

    like erica, shari, & leandra, shorts >>> pants! my legs are my favorite part of my body so i love showing them off when it’s finally warm enough to do so. i’m pretty open to wearing any type of shorts, but as i’ve been cleaning out my closet for the past year or so, my only options are tight, high-waisted, & denim.

    i didn’t get the longer pair until recently, so my only option for shorts were the short shorts. glad i have a mom-jean option for when i’m going for an unsexy vibe lol!

    • Harling Ross


  • stinevincent

    Shorts are as close as I can get to dancing around town in my underwear, so I love them. My favorites are an old pair of boys’ black suit pants that I cut off and re-hemmed. They fit like Harling’s with a few pleats. Not gonna lie, though, I also go for tighter short shorts, looser short shorts, and longer tight shorts (men’s). I can’t wait to see what pants I impulse cut off this spring!

  • gashgoldvermillion

    Leslie!!! I call ’em coochie crunchers. I love the pocket hanging out too. Perfection (if you can handle the crunch).

  • Chelle

    I’ve always been super tall so shorts anxiety runs deeeep, even now as a grown a$$ woman. Adults would always comment on how inappropriate shorts looked on me as a kid/teen even if they were slightly above the knee, and if I got longer ones they wouldn’t fit my (nonexistent) hips-so I avoid them completely.

  • Caro A

    Last year on my facebook I asked, “Are shorts even cute?” and let me tell you, it was one of the most popular posts I have ever posted. Thank you for this.

  • dietcokehead

    Every year as summer approaches, I play that fun game with myself where I try on a bunch of shorts and then hate myself (but maybe buy a pair or two anyway). Just finished the 2017 tourney about 48 hours ago. I don’t get it — I’m a miniskirt girl! Why the fuck do shorts make me feel like this? Although I got a loose, embroidered, practically skortlike pair this spring at Target, and they actually made me feel awesome. Please use MR influence to make skorts great again.

  • Kay Nguyen

    I prefer short shorts that are high waisted! Being a shorter girls with somewhat big legs aren’t the most flattering for shorts 🙁

  • Kattigans

    When I was a kid/teenager/in college (I lived in SoCal), I LIVED for shorts season. I had a pair of neon pink corduroy pair in college I was clued into. I’ve always loved shorts more than pants, however lately, now as a 25 y/o I’m having shorts anxiety. I have a few pairs I like that are all a little different, but I start to kinda internal freak out whenever I slide them on. I’m still experimenting so this is great inspiration to get out there and let my shorts freak flag fly

  • CatMom

    All my shorts anxiety comes from other people, honestly. I live in New York and as anyone who lives here (or in any large city) knows, catcalls are A Thing. And I know that me being catcalled isn’t my fault, but I’ve got a big butt and big thighs and when I wear shorts, the catcalls get a lot worse. Especially if I’m wearing platforms or anything that can be construed as a heel! So I don’t really have anxiety about the shorts per se, or even about how my body looks in shorts – I just stress about wearing them because of other people 🙁

  • belle

    i can’t remember the last time i wore shorts. i don’t even like exercising in them!! i am insecure about my pudgy, so-pale-you-can-see-veins legs, but i also find shorts so uncomfortable – my legs get sweatier in summer, yet get cold in air conditioning, and i cannot STAND the idea of my bare legs touching public seating (like on the bus or in an airplane). plus you have to shave your legs…luckily there aren’t really any occasions in my life that call for shorts, and i am a huge fan of a flowy pant, dress, or relaxed trouser!

  • Anna

    I guess I have shorts anxiety. But not because I don’t like my legs or my butt or whatever. I like my body and wear short dresses and skirts. But with shorts it’s different. I just don’t like the way they look. However, I used to have a pair of velvet shorts that were pretty flattering. Dark blue velvet, high waisted, very short and fitted but not too tight. However, I only wore them over tights when going out dancing. So for summer, I prefer dresses or pants made out of light fabrics.

  • Elizabeth

    Hi. My name is Eli. I’m 21 years old and I suffer from shorts anxiety. It has never been an issue in that I live in a cold country but this summer I am venturing to a new country and soon to experience a summer that is actually warm (!!!) and so shorts are a fear I must conquer. It’s weird because I actually like my legs but I just hate shorts. I’m thinking of trying one of those billowey pairs that sort of look like a skirt to ease myself into the whole thing. Pray for me.

  • Senka

    My sentiments towards shorts are very similar to Haleys. I don’t like them very much, and the older I get the less of a friend they are. Cut offs were never my thing, and I did try many times. Once I got enthusiastic and bought leather high waisted shorts from zara, only to never put them on, and eventually donate them. But every year come vacation time, I find my self in need of a holly grail shorts and my search begins. Last summer I settled for some structured, wide legged and high waisted off-white ones that did the job. I didn’t feel like million dollars in them ( The fact is I only do in dresses, if ever) but they served the purpose of me looking like any tourist on any summer destination ever, and being comfy and not melting.

    • But even when you find your holy grail shorts, your body might fail you! I had the perfect pair last year and was on the hunt for another…Then I gained like 8 pounds over winter and my HG shorts make me feel fat! 🙁

      • Senka

        Yep. And also mental and physicall anguish of trying to suck my waist in so I can button them and not get new ones, because I hate shopping for them.

  • beccamu

    my shorts anxiety is stemmed from the cat-calling implications. why do i feel so vulnerable with my legs exposed?

  • Nicole

    Not even two weeks ago I was sort of having this same dialogue with myself and accepting the fact that shorts just aren’t for me which is fine cause I can just find other stuff to wear when it gets hot that don’t make me feel self conscious, like a breezy wide-legged pant or midi skirt or literally anything else other than shorts, but this article was a good reminder to keep an open mind and it’s so comforting to know that I’m not the only one with shorts anxiety hahaha

  • Selina Moses

    I hate shorts but then there’s not much need for it in London. We tend to wear them with tights in Autumn but bare legs and shorts scare me. I don’t know if I’ll be brave enough to wear shorts really. Only on a hot beach holiday I will wear them but it has to be boiling for me to do that

  • Just had a “Wow! You’ve been reading MR a long time” moment when I knew exactly what style Leandra was going to choose upon reading the title. Harling’s style of shorts are my go-to for summer! Hoping I can sneak them into the office with a bit more length. 🙂

    Thanks for continuing to expand and inspire MR staff!