So, You Bought a Pair of Bike Shorts? Here Are 5 Ways to Wear Them

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Bike shorts, they’re just like leggings...right? In theory, yes. They’re simply the cut-off versions of the athleisure you pretty much live in all winter long. But when it comes to actually figuring out how to wear them, well, you’ll quickly find that bike shorts are not quite as easy to wear as your go-to Lululemon tights.

I first acquired a pair of bike shorts last year—picking a trusty all-black version from Amazon—and spent workdays and weekends figuring out how to rock my new stretchy acquisition. I’m not going to lie, it was a bit of a challenge, even though I quickly learned that they looked great with a T-shirt and a tailored blazer for the office and figured out that they actually look kinda cool with a clunky sneaker for weekend errands.

Once summer 2020 rolled around and the trend returned for another year, I shed my initial skepticism and emerged a bike shorts expert. I acquired a handful of new pairs, including those in shocking colors and cool prints and tried styling them in a ton of creative ways. So, for all those new to these shorts—and for those who are familiar but just want some new styling tips—here are five of my go-to bike shorts outfits whether I’m hitting the trails...or the couch.

See Ya, Short Shorts—Here’s What’s Taking Over for Summer 2020

bike shorts button down
Dena Silver

1. Oversize Button Down + Short Shorts

When all of my denim cut-offs are in the wash (it happens more often than you might think), I tend to throw on a pair of short bike shorts and an oversized button-down. Especially when I’m headed to the beach after a long day at work, since they’re fuss-free and not much more fabric than a bikini bottom. FYI, this blouse was a vintage find and cost around $8, but it’s my favorite beach piece—especially when I inevitably end up staying to watch sunset and need an extra layer to keep me warm.

Get the look: Madewell shirt ($80; $55); Athleta shorts ($50; $35); Poolside Bags tote ($175); Dr. Scholl’s slides ($80); Valentino sunglasses ($430)

bike shorts white blouse
Dena Silver

2. Blouse + Tie-dye Bike Shorts

It’s an undisputed fact that bike shorts are the best item to wear when running an errand when the forecast threatens 80 percent humidity. And it definitely doesn’t hurt that this Tory Sport pair comes in the trendiest pattern of the season: tie-dye. I like to dress mine up with a breezy white blouse, making sure it hits just below the hip, for the most flattering fit possible. I tend to throw on a pair of white leather sneakers and finish off the look with a structured purse, both of which lend a dressed-up air to my adored loungewear.

Get the look: Saylor top ($220); Tory Sport shorts ($68); Ratio et Motus bag ($568); Cole Haan sneakers ($130); Urban Outfitters sunglasses ($18); Machete hoops ($68)

bike shorts long sleeve tee
Dena Silver

3. Tie-dye Tee + Basic Bike Shorts

I’m going to be honest, this is probably my most worn outfit this summer. While an oversized T-shirt with bike shorts feels way too ‘90s (and like something my grandma used to wear), simply add sleeves to the top and it feels totally modern. For Tuesdays packed with Zoom meetings and Saturdays spent cleaning the house, this easy look has become my go-to. From the waist up it looks pulled together, but it’s certainly rugged enough to handle all those not-so-glamorous household duties. Like taking out the trash.

Get the look: Spiritual Gangster shirt ($98); Yogalicious bike shorts ($25); Vincero watch ($140); Vagabond Shoemaker sandals ($120); Anthropologie sunglasses ($38)

bike shorts sweatshirt
Dena Silver

4. Cozy Sweatshirt + Matching Bike Shorts

There’s something about the subtle matching of the cream-colored Rails sweatshirt and the stripe down the side of these Aritzia shorts that makes this combo feel less like sweats and more like a look. In fact, I wear these two pieces together exclusively, because it allows me to take all the guesswork out of getting dressed in the morning. This is a tried-and-true combo that has yet to let me down—save for the one time I spilled sriracha all over this cream-colored ensemble.

Get the look: Rails sweatshirt ($138); Aritzia shorts ($48; $24); Freedom Moses sandals ($45); Jennifer Fisher hoops ($350); Karen Walker glasses ($220)

bike shorts sports bra
Dena Silver

5. Sports Bra + Matching Bike Shorts + Denim Jacket

Yes, I do feel like Sporty Spice in this two-piece workout set, thank you so much for asking. Whether I’m going for a hike or for an easy walk on the beach, I tend to favor this Outdoor Voices duo and not exclusively because they’re Kermit green. It’s actually because the compression fabric makes me feel zipped in but never digs into my thighs or my armpits. It also never shows sweat, which is an absolute godsend. Regardless, I tend to keep a denim jacket in the car when I wear this set out, so I can feel a touch more covered up when I inevitably stop for an ice cream cone on the way home.

Get the look: Outdoor Voices bra ($68); Outdoor Voices shorts ($58); J.Brand denim jacket ($348); Caraa waistbag ($95); Hoka One One sneakers ($160); Persol sunglasses ($345; $173)

dena silver headshot

Fashion Editor

From 2019-2021 Dena Silver held the role of Fashion Editor covering product recommendations, trends, and what you should be shopping this season.