How to Wear Long Shorts Without Looking Like You're in P.E.
Styling tips, outfit formulas and my roundup of flattering pairs to wear now
If you’ve been eyeing longer shorts - trouser shorts, board shorts, or anything grazing your knee but aren’t sure how to wear them without feeling like you're back in gym class, this one’s for you.
They’re basically the shorts version of your go-to trousers you’ve been wearing all winter. Just as easy to style, with the added bonus of a breeze that flies up to your crotch for some ventilation. Vag-friendly shorts, as Chloe Fineman so perfectly put it.
Key Points:
The Right Shape: Look for a little flow or volume, you want a decent leg opening at the hem. The bigger the leg opening, the slimmer your legs will look. If it’s too straight, the leg opening will be more narrow and not as flattering on your legs. You also want to look for shorts that have a pleat at the princess seam (usually located under where the belt loops would be).
Length Sweet Spot: Aim for the shorts to hit right at mid-knee. Showing this part of the leg keeps the silhouette flattering and covers any upper knee fat (it’s one of my least fav parts on myself, bless you if you love your knees). If the shorts are too long, the length hits at your mid calf, accentuating the widest part of the bottom of your leg.
Rise: Another thing I’ve noticed about all the long shorts I love: they sit lower on the waist. They don’t have to be super low-slung, but a high-waisted long short can make you look a bit round when you don’t have the extra length (of a pant) to balance it out. I’d recommend sizing up or looking for a pair that’s not intentionally designed to be high-rise.
Shoes: Almost everything works… sandals, loafers, mules — but I find the most flattering option is a flip-flop shape that leaves your ankles fully exposed. It helps your legs look longer. Sneakers can work too, but sometimes feel a little too literal (like you just left soccer practice), so balance the rest of the outfit accordingly.
I’ve been collecting longer shorts for a while, so most of the ones in my closet are vintage or older pieces that aren’t available anymore. But at the bottom, I rounded up some current options with a great shape, flattering fit, and the right length to wear and lurve.
Below are a few ways I’ve styled mine, plus some tips to help you style yours. Starting with…
Your classic trouser shorts. They go with pretty much anything a trouser would, and the ecru color is an easy neutral to build around. I’ve styled them with various tops and tees, both with flats and heels for your viewing pleasure.
Below I styled the same shorts with two different striped button-downs. On the left, I tucked the front and overlapped it into the waistband to create a kind of surplice shape. I like separating the fabric on this one and letting the t-shirt shine, otherwise the bold stripes felt overwhelming. On the right, I left it untucked but tucked a bit of fabric in the back to give it some waist shape. In both looks, I layered the Everlane grey tee underneath.
Here I styled a pair of old DVF shorts that never made it into production. They’re a blue silk crepe and a bit straighter than I usually go for (since they don’t have pleats). Because they’re silk, I like pairing them with a cotton tee or sweater, something to offset the dressiness of the silk and make them feel more wearable.
Next up are the board shorts from Donni. I’ve always loved surf shorts. And I know they’re having a moment right now, but these are really reallyyyy gr8. It’s v cool that Alyssa chose to design them in taffeta, it’s a refreshing shake up from the usual nylon or tech fabrics you’d expect. It makes them feel more innovative and fun to wear. The drawstring gives them a casual vibe, so I like dressing them up with a boho blouse.
I love pairing a long sleeve with shorts. It’s a good balance when you’re baring your legs. I styled this pair with my beloved striped polo (mentioned in this newsletter) and also with a v-neck long sleeve that doubles as a lightweight spring knit. I layered it over a crewneck tank, which adds just the right amount of contrast. One of the best things about these shorts is how easily they work with so many different shoes…
They sit low on the hip, as a board short should! I was on the phone with my friend Abigail, and she suggested I try a boxer short underneath. I only have a light blue pair, and the light blue / light yellow combo looked too babyish, so I went with a white jersey short instead. Kind of into it. I am wearing a Loewe x Paula’s Ibiza watermelon top from a few seasons ago.
Lastly, I styled the board shorts with a button-down to show one more way to wear them. There’s pretty much nothing a button-down doesn’t work with, or make look better. So when in doubt, just throw one on.
I got the longer boxer shorts below at the Balenciaga sample sale with my friend Rebecca. They’re poplin, so I styled them with a silk cami. I like the contrast of something more refined against the casualness of the cotton. They’d also look great with a button-down (obv). I rolled the waistband down to create a natural pleat, which made the shorts flare out a bit more… and I’m into it (picture 1 vs. picture 2 shows the difference: waistband left alone vs. rolled down).
These next ones are much longer than I’d typically recommend buying, but they work because of the exaggerated A-line shape and generous leg opening, which makes them feel more like a skirt. I found these puppies on Poshmark. Both the top and the shorts are Rosie Assoulin from years ago. I tracked down the top on TRR in a medium and there’s another color way of it here in an XS. I’m wearing a medium (I normally take a small… it’s definitely too big, but it was the only one I could find and I had to have her).
and for the recs…
I rounded up some great trouser shorts and long cotton styles. All with the right shape, flattering fit, and (not too long, not too short) length that hits at the knee. All of these are cotton, linen or twill blends, so they’re breathable and will treat you right as the weather continues to warm up.
As always, wear what makes you feel your best.
xx
Kelly
How did you know that I was wondering if I could pull off long shorts and how??? These are all amazing! I want the Rosie assoulin pants so much
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