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

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.

There’s a lot of product out there, some would say too much. No doubt this has left you with an overwhelming set of questions about the latest must-haves. Luckily we’ve got answers. At Refinery29 we are here to help you navigate this epic world of stuff. All of our editorial market is independently selected and curated by the team. But if you buy something we link to on our site Refinery29 may earn commission.

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.

Dries Van Noten shorts.

Samantha Pleet Tabernacle Sandal Lemon, $250, available at Samantha Pleet

The Frankie Shop White Button Up Midi Dress, $169, available at The Frankie Shop

Atelier Mimii Valerie Bag, $320, available at Atelier MimiiPhotographed by Savanna Ruedy.

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.

Dries Van Noten shorts.

The Frankie Shop White Button Up Midi Dress, $169, available at The Frankie ShopPhotographed by Savanna Ruedy.

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.

Vintage bag; W Concept shoes.

Tach Clothing Delmira Silk Top, $110, available at Tach Clothing

Eric Emanuel EE Basic Short, $88, available at Eric EmanuelPhotographed by Savanna Ruedy.

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.

Tach Clothing Delmira Silk Top, $110, available at Tach Clothing

Eric Emanuel EE Basic Short, $88, available at Eric EmanuelPhotographed by Savanna Ruedy.

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.

Vintage blazer and bag; Moon Choi shorts; Céline shoes.

Photographed by Savanna Ruedy.

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.

Vintage blazer and bag; Moon Choi shorts.

Photographed by Savanna Ruedy.

The What-Even-Are-These Shorts
It’s a Bermuda shor t! 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.

Vintage bag.

Urban Outfitters Cindy Chambray Bra Top, $19.98, available at Urban Outfitters

Muji Women Seamless Jersey Short Sleeves Pajama, $34.29, available at Muji

Gimaguas Limon Earrings, $30, available at GimaguasPhotographed by Savanna Ruedy.

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?

Vintage bag.

Urban Outfitters Cindy Chambray Bra Top, $19.98, available at Urban Outfitters

Muji Women Seamless Jersey Short Sleeves Pajama, $34.29, available at MujiPhotographed by Savanna Ruedy.

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