How To Wear Gym Shorts Like A Fashion Editor

Having spent the latter half of my life dabbling in one sport or another (there was my soccer era, my volleyball stint, my short-lived track career, and now, my run-for-fun era), my gym shorts drawer contains a full wardrobe of styles, with every length, color, and fabric represented. And with so many great looks at my disposal, it feels like a shame to relegate the workout mainstay to lazy weekends or an evening boxing class.

Sporty shorts — basketball, running, and the like — are surprisingly well-suited to pairing with more structured, formal items. (See: trendsetters like Bella Hadid and Hailey Bieber, who’ve made a habit of dressing them up in unique and stylish ways.) Sure, it might feel counterintuitive to wear them for a night out (with heels, no less) but I’m here to say that it can be done — all it takes is a little creative thinking. Sometimes that might mean wearing Nike running shorts with a blazer and cowboy boots; other times, it might mean throwing on a lightweight nylon pair and a button-down. Here, four playful ways to style the athleisure staple.

Y2K-Inspired

This is my second time living through the Y2K style era, and at 32 years old, I’m embracing baby tops and baggy shorts just as earnestly as I did the first time around. Part of what makes this sport-short combo so much fun is its utilitarian playfulness. Chunky hiking sneakers mean I could climb a mountain (or at least the hill to my Brooklyn apartment) in my sheer shirt and basketball shorts. Odds are, however, you’ll find me sitting at a local coffee shop doing my best to blend in with the cool Gen Z art students I call neighbors.

Pretty Cottagecore

Having owned the same pair of Nike Tempo Shorts since high school, I’ve found myself wearing them for plenty of unexpected occasions, including a few dressy get-togethers. Sporty shorts may, admittedly, not seem like the most natural mate for a flouncy top and strappy sandals, but I revel in the idea of playing with unexpected groupings.

Quirky Corporate

Now that I work from home, all bets are off when it comes to workwear. If I could envision an outfit that embodies my best corporate self, it would be this — playful and sporty, yet refined. My white running shorts have a light, airy feel, while the mohair vest and wool blazer feature lusher textures — a tactile play in opposites. Adding cowboy boots, instead of your usual streamlined black booties, adds a fun finishing touch that’s subtle enough to keep the look from feeling costume-y.

Laid-Back & Preppy

This time of year my casual summer style starts to give in to cravings for structured tailoring. When I’m straddling these two states of mind, my go-to look is a classic striped button-down paired with lightweight nylon shorts. It’s athletic with a preppy twist, it’s corporate with a casual bent, it’s Zoom on the top and soccer pitch on the bottom. These days, however, a Zoom-only combination simply isn’t enough; shoes have to make it into the equation — in this case, a pair of G.H. Bass penny loafers.