Comfortable Walking Shorts

Comfortable walking shorts are the perfect companions for any outdoor adventure, offering a blend of style and practicality that makes them a must-have in any wardrobe. Designed with both comfort and versatility in mind, these shorts are ideal for everything from casual strolls in the park to more vigorous hikes. With an array of colors and styles to choose from, finding the right pair to match your personal taste is a breeze. Whether you're exploring new trails or enjoying a laid-back day in town, comfortable walking shorts ensure you stay relaxed and ready for whatever the day brings.

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298 Items

Men's Tropic-Weight Cargo Shorts, Comfort Waist, 10"

A pair of lightweight, breathable 100% cotton cargo shorts with elastic side panels in dusty olive.

Pros: High quality Perfect fit Lightweight Deep pockets Comfortable
Men's Tropic-Weight Cargo Shorts, Comfort Waist, 6"

A pair of gray cotton cargo shorts with a comfort waist and 6" inseam for all-day ease.

Pros: Lightweight fabric Durable quality Versatile style Ample pockets Comfortable fit
Men's Lakewashed® Stretch Khaki Shorts, 9"

A pair of heritage khaki shorts in 98% cotton and 2% spandex for ultimate comfort and flexibility.

Pros: High quality Perfect fit Durable Comfortable Breathable
Men's Dock Shorts, 8"
Price was from: $49.95 now: $34.99

A pair of brown cotton shorts with an elastic drawstring waist and an 8" inseam for comfort.

Pros: Lightweight and durable High quality Versatile design Great color options Comfortable fit
Men's Tropic-Weight Cargo Shorts, 10"
Price was from: $49.95 now: $39.99

A pair of lightweight, breathable 100% cotton cargo shorts with a 10" inseam and multiple secure pockets.

Pros: High quality Lightweight Versatile Good fit Comfortable
Men's Wrinkle-Free Double L® Chino Shorts, Natural Fit, Hidden Comfort Waist, 8"

A pair of wrinkle-free khaki shorts with hidden elastic waist, made from premium 100% cotton.

Pros: Wrinkle-proof fabric High quality Perfect fit Comfortable waistband Durable
Women's Vista Camp Bermuda Shorts

A rugged, lightweight blue Bermuda short with UPF 50+ protection and a comfy elastic waistband.

Pros: Flattering and versatile style Lightweight and breathable fabric Quick-drying and easy care Deep and zippered pockets Comfortable fit
Men's L.L.Bean Multisport Shorts, 9"

A pair of alloy gray, quick-dry, stretchable shorts with UPF 50+ protection and multiple pockets.

Pros: Great fit Quick-dry fabric Lightweight shorts Versatile Comfortable
Men's Wrinkle-Free Double L® Chino Shorts, Classic Fit, 8"

A pair of dark khaki, wrinkle-resistant cotton shorts with an 8" inseam and classic fit.

Pros: Great fit High quality Durable Comfortable Nice color
Men's Lakewashed Stretch Khaki Shorts, Pull-On, 8"
Price was from: $49.95 now: $39.99

A pair of khaki pull-on shorts with an 8" inseam, made from 98% cotton and 2% spandex.

Pros: Solid construction Perfect fit Durable Versatile Comfortable
Men's Tropicwear Shorts, 9"

A pair of soft sand nylon shorts with a 9" inseam, offering sun protection and comfort.

Pros: Great fit Stylish look Secure pockets Lightweight material Comfortable
Men's Explorer Ripstop Shorts, 8"
Price was from: $69.95 now: $59.99

A versatile red short with moisture-wicking, abrasion-resistant fabric and secure zippered pockets for active comfort.

Pros: Great fit Lightweight Neat appearance Durable Comfortable
Men's L.L.Bean Multisport Shorts, 7"

A versatile pair of green shorts with stretch, quick-dry fabric, UPF 50+, and multiple pockets.

Pros: Perfect fit Wrinkle resistance Comfortable material Deep pockets Lightweight design
Men's Lakewashed® Stretch Shorts, Pull-On, Chambray, 8"
Price was from: $49.95 now: $39.99

A pair of dark chambray pull-on shorts with an 8" inseam, made from 98% cotton and 2% spandex.

Pros: Great fit Convenient pockets Comfortable material Nice color Stylish appearance
Women's Tropicwear Comfort Shorts

A lightweight, tan short made from recycled polyester blend, offering UPF 50+ sun protection and quick-dry comfort.
Men's Tropicwear Comfort Shorts, 8"

A lightweight tan short made from recycled polyester blend, offering UPF 50+ sun protection and water resistance.
Men's VentureSoft Shorts, Print, 8"
Price was from: $59.95 now: $24.99

A sea green camo short with UPF 50+ protection, made from a moisture-wicking polyester-spandex blend.
Men's Ripstop Hybrid Shorts, 7"
Price was from: $69.95 now: $54.99

A versatile pair of green shorts with UPF 50+ protection, made from recycled nylon and spandex.
Men's Sunwashed Cotton Shorts, 8"
Price was from: $59.95 now: $44.99

A pair of sand dune cotton blend shorts with an 8" inseam and elastic waist for comfort.
Men's Explorer Ripstop Shorts, Fixed Waist, 8"

A rugged tan short with a fixed waist, moisture-wicking fabric, and modern styling for versatility.
Men's VentureStretch Chino Shorts, 7"

A versatile 7" tan chino short with UPF 50+ protection, made from a durable nylon-spandex blend.
Men's Everyday Poplin Shorts, Standard Fit, 8"

A lightweight green cotton-blend short with built-in stretch, perfect for warm days and easy movement.
Men's Ultralight Adventure Shorts, 8"
Price was from: $69.95 now: $59.99

A pair of dark bronze, ultralight men's shorts with a supportive inner brief and quick-drying fabric.
Men's L.L.Bean Multisport Training Shorts, 7"
Price was from: $69.95 now: $59.99

A pair of ultracomfortable, quick-drying black training shorts with a 7" inseam and UPF 50+ protection.

Comfortable Walking Shorts

There’s something about a great pair of walking shorts that makes every step feel easier, whether you’re strolling through the neighborhood, exploring a new city, or chasing after little ones at the park. As summer days stretch long and warm into August, comfortable walking shorts become a go-to essential—versatile enough for impromptu picnics, quick errands, or relaxed weekends with family and friends. When you’re choosing the right pair, it’s worth considering more than just style; think about how the fabric moves with you, how the waistband feels after a few hours, and whether the pockets are roomy enough for your keys, phone, or a handful of wildflowers picked along the way. The best walking shorts are designed to keep up with your day, offering lightweight comfort and durability that stands up to repeated wear and countless adventures. They’re the kind of staple you’ll reach for again and again, season after season.

Walking shorts also make a thoughtful and practical gift for anyone who appreciates time spent outdoors or values comfort in their everyday routine. They’re a welcome addition to any wardrobe, fitting seamlessly into the lives of active grandparents, busy parents, college students heading off to campus, or anyone who loves to travel light. Imagine gifting a pair to a friend before a big trip, knowing they’ll be able to wander cobblestone streets or hike scenic trails in comfort. The right pair of shorts can even inspire new routines, like early morning walks with a neighbor or after-dinner laps around the block. And because walking shorts are easy to pair with tees, polos, or lightweight button-downs, they offer endless possibilities for mixing and matching—ideal for those who value both practicality and timeless style.

As you browse this collection, you’ll find options designed with thoughtful details like adjustable waistbands, breathable fabrics, and reinforced stitching for lasting value. Whether you prefer a classic look or something with a bit more technical performance, there’s a pair here for every preference and every pace. And if your adventures take you off the beaten path, you might want to explore our selection of Comfortable Hiking Shorts—crafted for even more durability and versatility on rugged terrain. However you spend your summer days, comfortable walking shorts are a simple way to make every outing a little more enjoyable, letting you focus on the moments that matter most.