I don’t have a boyfriend, but if I did, his boxer shorts might be mysteriously disappearing from his underwear drawer this summer. Recently, all the cool girls I follow on Instagram have been styling boxer shorts with more elevated staples like boots, cardigans, and blazers—evoking a very Serena van der Woodsen for the 2020s vibe. She wakes up late, so she throws on whatever she can find on Nate’s floor and somehow leaves the Empire looking effortless and impossibly chic. Practically speaking, boxer shorts are an excellent choice for summer because they allow for decent air circulation and are usually made from breathable fabrics. Below, we compiled three ways to style boxer shorts for occasions of varying formality—whether you’re literally rolling out of bed to grab a coffee at your corner bodega or meeting friends for dinner.

White Tank + Blazer + Cowboy Boots

Photo (R): Courtesy of @izzipoopi

This is a fabulous outfit if you want to look cool and put-together albeit the mini hangover you may be experiencing. With the My Year of Rest and Relaxation movie on the horizon, this combination is about to explode in popularity—so start rocking it now.

Colorful Sweater + Sneakers

Photo (R): Getty Images

This combination is perfect for meeting your friends at the park. It’s low-key and comfortable, but the colors and statement sunnies add a fun flare, plus the strategic layering allows this look to work in a variety of temperatures.

Rib-Knit Wool-Blend Cardigan

$1,695 $1,695 at Saksfifthavenue

The Linen Boxer Short

$50 $50 at Everlane

Mini Jodie Leather Hobo Bag

$2,500 $2,500 at Saksfifthavenue

Athletic Court Sneakers

$130 $130 at Farfetch

Tortoise-Shell Pilot Sunglasses

$264 $264 at Farfetch

Buy at Coveteur

Bright Button Down + Pumps

Photo (R): Getty Images

Who says you can’t wear boxers and pumps? There’s something super sexy and daring about this mix of casual and formal, and the bright colors and statement necklace add a fantastic "wow factor."