How To Wear The Awkward-Length Shorts You Think You Can’t Pull Off

I Turned A Kiddie Pool Into A Professional Studio By​ Kyle Braun

Shorts, by nature, are pretty awkward. As an adult, I find that it’s consistently tricky to strike that balance between laid-back cool and kindergartener-headed-to-summer-camp. But with denim diapers a thing of the past (thank God!), Bermudas are threatening a comeback, as are athletic shorts and not-quite culottes. So, what’s a non-shorts-fan to do?

Like me, perhaps you don’t mind a classic pair of denim shorts, but as soon as a pair brushes your knee you’re all, “count me out.” There are a plethora of strange, in-between shorts out there that most of us think we can’t and won’t pull off (it’s why so many people avoid wearing shorts altogether). So from bloomers to borderline capris, I challenged myself to make these ‘weird’ bottoms work. And, with the right styling, dare I say, I did it? While I’m the first to admit to being picky with my shorts, this summer, I’m embracing their many different lengths — and I’m not looking back. Turns out I may be an any-type-of-shorts girl after all.


The Bloomers
Pants: who needs ’em? Even before bike shorts really stuck, designers from Marc Jacobs to Miu Miu have sent short-and-tight bloomers down the runways time and time again, leaving us to wonder if we really can leave the house sans pants. And though this is one style I never thought I’d dabble in, there is a way to make it work IRL.

Unless you want to flash some lower butt-cheek, allow me to recommend wearing bloomers underneath one of the summer’s many front-button dresses or skirts. (This way, they’re there when the subway grate kicks your dress.) For a retro feel, opt for a pair that has the cut of a vintage bathing suit bottom (and as for wearing underwear underneath, well, that’s a personal decision). Still, this breezy look is perfect for those 100-degree-and-muggy days when jeans (or any type of pants, for that matter) just aren’t an option.

The Basketball Shorts
From oversized swim trunks to other elastic-waist pieces, warning: this season’s athletic shorts may cause flashbacks to those college walk-of-shame days. And I don’t know about you, but that is one look I never want to revisit. But the key to making this style work? An unexpected, more dressed-up look that doesn’t make you look like you just rolled out of bed.

I paired these Eric Emanuel shorts with a sheer black top, mimicking a look from one of my favorite streetwear style gurus Anaa Saber. As soon as she showed up at a fancy fashion dinner wearing a version of this look, I knew basketball shorts weren’t just reserved for the court.

The ’80s Yuppie
The ’80s called, they want their trends back — but not before I get my hands them. Earlier this summer, I decided to give shorts suits a try, and now I’m hooked. And while these shorts may be longer than most would be willing to wear, the fact that it comes with a matching blazer makes styling a no-brainer.

For the shorts, look for a right-above-the-knee length that’s neither too long or too short; that way, you won’t have to deal too much thigh sweat. And since I don’t see the suit trend slowing down, even in the heat of summer, there’s no time to embrace the trend like now.

The What-Even-Are-These Shorts
It’s a Bermuda short! It’s a pair of capris! It’s…neither of those things? This is one awkward pair of shorts! And while they’re actually a part of a pajama set from Muji, I was determined to make them work for more than just lounging around.

Something just felt right to pair these long-length shorts with an extra-cropped crop top. They’re a fresh change of pace from the typical shorts I’m drawn to, and boy, are they a conversation-starter. But is there anything better than embracing the weird in life, shorts included?