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Comfortable shorts for men are all about keeping your vibe easy and your style on point—whether you’re chilling at home, heading out with friends, or catching some sun. Find fresh new styles and effortless fits that move with you from beach days to street hangs. With the best assortment of trending looks and laid-back favorites, Tillys is your go-to destination for comfortable shorts for men that keep you looking cool and feeling even better. Style with confidence and discover your next go-to pair right here.
$49.99
Now $22.39 (55% Off)

SALE!

A pair of black fleece sweat shorts with a bold graphic, elastic waistband, and side pockets.

$49.99

A pair of black, stretch-woven shorts with sweat-wicking, water-repellent fabric and an elastic waistband.

$34.99
Now $24.49 (30% Off)

SALE!

A pair of black hybrid shorts with 4-way stretch, featuring slant hand pockets and dual back welt pockets.

$49.99

A versatile pair of grey shorts with an elastic waistband, 7'' inseam, and on-seam hand pockets.

$34.99
Now $20.99 (40% Off)

SALE!

A pair of black polyester mesh shorts with an elastic drawstring waist and welt hand pockets.

$34.99
Now $14.99 (57% Off)

SALE!

A stylish pair of black chino shorts with a 7" inseam, made from cotton, recycled polyester, and spandex.

$34.99
Now $24.49 (30% Off)

SALE!

A pair of dark khaki hybrid shorts with 4-way stretch, featuring slant hand and dual back welt pockets.

$34.99
Now $14.99 (57% Off)

SALE!

A light grey 7" chino short with slant hand pockets, made from cotton, recycled polyester, and spandex.

$34.99
Now $14.99 (57% Off)

SALE!

A pair of dark olive nylon shorts with elastic drawstring waist and multiple pockets.

$34.99
Now $14.99 (57% Off)

SALE!

A pair of desert-colored mid-length chino shorts with a 9" inseam, made from cotton, recycled polyester, and spandex.

$34.99
Now $14.99 (57% Off)

SALE!

A pair of khaki chino shorts with a 7" inseam, featuring slant pockets and a zip fly.

$34.99
Now $9.97 (72% Off)

SALE!

A light grey mid-length chino short with a 9" inseam, featuring slant hand pockets and dual back welt pockets.

$34.99
Now $14.97 (57% Off)

SALE!

A pair of khaki chino shorts with a 10" inseam, made from cotton, recycled polyester, and elastane.

$29.99
Now $13.99 (53% Off)

SALE!

A pair of agave-colored twill shorts with an elastic waist, made from 98% cotton and 2% spandex.

$44.99
Now $31.49 (30% Off)

SALE!

A pair of khaki chino shorts with a 10.5" inseam, made from recycled polyester and cotton.

$39.99
Now $27.99 (30% Off)

SALE!

A pair of charcoal nylon shorts with an elastic waistband, perfect for workouts or casual wear.

$39.99
Now $19.97 (50% Off)

SALE!

A pair of black twill cargo shorts with an elastic waistband and multiple pockets for storage.

$34.99
Now $24.49 (30% Off)

SALE!

A versatile black 4-way stretch short with elastic waistband and zippered back pocket.

$34.99
Now $24.49 (30% Off)

SALE!

A versatile pair of black chino shorts with a comfortable cotton-spandex blend and practical pockets.

$54.99

A lightweight, black mesh short with a relaxed fit and adjustable waistband for all-day comfort.

$34.99
Now $14.99 (57% Off)

SALE!

A pair of surplus-colored chino shorts with a 5" inseam, made from cotton, recycled polyester, and spandex.

$34.99
Now $14.97 (57% Off)

SALE!

A storm blue chino short with a 5" inseam, made from cotton, recycled polyester, and spandex.

$34.99
Now $14.99 (57% Off)

SALE!

A stylish pair of black chino shorts with a 5" inseam, made from cotton, recycled polyester, and spandex.

$39.99

A light denim short with utility pockets, hammer loop, and a comfortable loose fit.

Comfortable Shorts For Men

When the sun’s out and the days stretch long into golden evenings, there’s nothing quite like slipping into a pair of comfortable shorts. Whether you’re gearing up for a weekend road trip, hitting the skatepark with friends, or just chilling on the patio, the right pair of shorts makes all the difference. Comfort is everything—think soft fabrics that move with you, easy waistbands that don’t dig in, and fits that let you kick back or stay active without a second thought. In June, when the heat is on and plans can change at the drop of a hat, you want shorts that keep up with your every move. Breathable cotton, lightweight blends, and moisture-wicking materials are key for all-day wear—especially when you’re bouncing from the beach to backyard BBQs. For those who live in shorts all summer, versatility matters. Go for styles that transition effortlessly from casual hangs to spontaneous adventures, with pockets for your essentials and lengths that suit your vibe. If you’re all about that laid-back, California-cool look, relaxed fits and drawstring waists are a must. And if you’re shopping for someone else, comfortable shorts are always a solid gift—think grads heading off to college, dads who love their weekend downtime, or anyone who could use a fresh, easy upgrade to their summer wardrobe.

Comfortable shorts aren’t just about style—they’re about living your best life, whatever that looks like. Maybe you’re the type who’s always on the move, from early morning runs to late-night bonfires, or maybe you just want to keep things low-key with a soft tee and your favorite slides. Either way, the right pair of shorts is your go-to for effortless comfort and confidence. When you’re picking out your next pair, consider what your day has in store: quick-drying options for pool days, stretchy materials for active afternoons, or classic cuts that work just as well for grabbing coffee as they do for catching a sunset. And don’t forget about the details—adjustable waistbands, handy pockets, and lightweight fabrics all add up to a fit that feels just right. If you’re looking to keep things cool and breezy, check out our selection of Lightweight Shorts For Men for that barely-there feel that’s perfect for the hottest days. With so many options to choose from, finding your new favorite pair is just part of the summer adventure. Whether you’re gifting a pair to a friend or refreshing your own rotation, comfortable shorts are the ultimate staple for anyone who wants to make the most of every sunny moment.