Men's Comfortable Shorts

Men’s comfortable shorts are made for everything from backyard barbecues to laid-back afternoons on the trail. With timeless style and dependable quality, these shorts are designed to keep up with all your outdoor plans and everyday adventures. Explore a selection that’s as versatile as it is comfortable, offering lasting value and easygoing appeal for wherever your day takes you.

Sort by:

Filter & Sort

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

A pair of vintage indigo cargo shorts with breathable cotton fabric and elastic side panels for comfort.

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

A pair of tan, 100% cotton cargo shorts with a comfort waist and 6" inseam.

Pros: Lightweight fabric Durable quality Versatile style Ample pockets Comfortable fit
Men's L.L.Bean Allagash Cargo Shorts, 10"
Price was from: $64.95 now: $44.99

A rugged pair of brown cotton cargo shorts with multiple pockets and a 10" inseam for functionality.

Pros: Well-made construction Durable material Great color options Comfortable fit Roomy pockets
Men's Dock Shorts, 8"

A pair of vintage indigo shorts made from 100% organic cotton with an adjustable drawstring waist.

Pros: Lightweight and durable High quality Versatile design Great color options Comfortable fit
Men's Wrinkle-Free Double L® Chino Shorts, Natural Fit, Hidden Comfort Waist, 8"

A wrinkle-free, 100% cotton khaki short with hidden elastic waist and 8" inseam for all-day comfort.

Pros: High quality Durable fabric Wrinkle-free material Comfortable waistband Good fit
Men's Sport Shorts with SUPPLEX® fabric, 8"

A versatile pair of navy nylon shorts with UPF 50+ protection and quick-drying, anti-odor mesh liner.

Pros: High quality Attractive design Fast-drying material Comfortable Good fit
Men's Cresta Shorts, 10"

A lightweight gray nylon blend short with UPF 50+ protection, stretch comfort, and secure zippered pockets.
Men's L.L.Bean Multisport Shorts, 9"

A pair of classic black, 9" synthetic shorts with UPF 50+ and quick-dry, stretch comfort.

Pros: Great fit Quick-dry fabric Lightweight shorts 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 L.L.Bean Multisport Shorts, 7"

A versatile pair of gray shorts with stretch, quick-dry fabric, UPF 50+ protection, and secure pockets.

Pros: Perfect fit Wrinkle resistance Comfortable material Deep pockets Lightweight design
Men's Tropicwear Comfort Shorts, 8"
Price was from: $64.95 now: $44.99

A lightweight tan short made from recycled polyester blend, offering UPF 50+ sun protection and water resistance.
Men's L.L.Bean Multisport Training Shorts, 7"
Price was from: $69.95 now: $34.99

A pair of ultracomfortable, quick-drying training shorts with UPF 50+ protection and built-in boxer brief liner.
Men's Comfort Stretch® Chino Shorts, 8"

A breathable blue cotton/CoolMax blend short with built-in stretch and an 8" inseam for comfort.
Men's Wide-Wale Cord Pull-On Shorts, 7"
Price was from: $59.95 now: $44.99

An easygoing orange cotton-blend corduroy short with elastic waist, stretch, and soft, textured feel.
Men's Access Trail Shorts, 9"
Price was from: $64.95 now: $44.99

A versatile pair of green shorts with UPF 50+ protection, made from a quick-drying nylon blend.
Men's VentureStretch Chino Shorts, 7"
Price was from: $69.95 now: $44.99

A versatile gray short with a 7" inseam, featuring water-resistant nylon blend and UPF 50+ protection.
Men's Ripstop Hybrid Shorts, 7"
Price was from: $69.95 now: $34.99

A versatile red short with UPF 50+, made from recycled nylon blend for comfort and quick drying.
Men's Everyday Poplin Shorts, Standard Fit, 8"
Price was from: $64.95 now: $44.99

A lightweight gray cotton-blend short with built-in stretch and an 8" inseam for easy movement.
Men's Mountainside Ripstop Shorts, 8"

A pair of brown shorts made from a durable cotton-nylon blend with UPF 50+ sun protection.
Men's BeanFlex® Performance Canvas Shorts, 9"
Price was from: $74.95 now: $49.99

A rugged tan canvas short made from a soft, stretchy TENCEL cotton blend for everyday comfort.
Men's Field Chino Shorts, 7"

A rugged pair of gray chino shorts crafted from a comfortable, garment-washed cotton blend with stretch.
Men's Sunwashed Khaki Shorts, 7"

A pair of green peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.
Men's Sunwashed Khaki Shorts, 9"

A pair of blue peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.
Men's VentureStretch Five-Pocket Shorts, 9"
Price was from: $69.95 now: $44.99

A gray, abrasion-resistant nylon blend short with UPF 50+, water-repellent finish, and zippered security pocket.

Men's Comfortable Shorts

When the days grow longer and the sun sits a little higher in the sky, there’s nothing quite like reaching for a pair of comfortable shorts to make the most of your time outside. Whether you’re heading out for a family hike, walking the dog around the neighborhood, or relaxing in the backyard with friends, the right pair of shorts can make all the difference. Many people find that mens most comfortable shorts are the ones that move with you, offering just the right balance of breathability, flexibility, and durability. Features like stretch waistbands, lightweight fabrics, and reinforced seams help ensure comfort from sunrise to sunset, whether you’re playing catch with the kids or tending the grill on a warm evening. And for those who prefer a little extra freedom, comfortable short shorts can be a great option, providing a classic look that’s easy to dress up or down depending on the day’s plans.

Shorts are a wardrobe staple for a wide range of activities and occasions, making them a thoughtful gift for birthdays, Father’s Day, or just because. L.L.Bean men’s shorts, for example, are designed to stand up to everyday adventures, from impromptu beach trips to backyard projects. If you’ve ever wondered, “Can I wear shorts to this?”—the answer is almost always yes when you choose a versatile, well-made pair. Comfortable shorts are ideal for travel, too, packing easily and offering all-day comfort whether you’re sightseeing or exploring a new trail. For those who appreciate timeless style, options like Mens Casual Khaki Shorts blend classic looks with modern comfort, making them a go-to for everything from casual Fridays at the office to weekend gatherings. No matter where your plans take you, choosing shorts that fit well and feel great helps you stay focused on what matters most—enjoying the moment and the company you keep.

As you refresh your warm-weather wardrobe, think about the details that matter most to you—whether that’s a relaxed fit, moisture-wicking fabric, or plenty of pockets for your essentials. The best shorts are the ones that keep up with your lifestyle, offering comfort and confidence for every adventure. From early morning walks to late-night campfires, comfortable shorts are made for the shared joy of the outdoors, helping you create lasting memories with friends and family. And as the seasons shift and outdoor plans fill your calendar, having a reliable lineup of shorts on hand ensures you’re ready for whatever the day brings—whether it’s a spontaneous pick-up game, a scenic bike ride, or simply unwinding in the shade with a good book.

FAQs

Men’s comfortable shorts are often crafted from soft cotton, breathable linen, moisture-wicking synthetics, or blends that combine durability with a gentle feel. These materials are chosen for their ability to provide long-lasting comfort, resist wear and tear, and offer flexibility for a wide range of activities.

Yes, features like multiple pockets, adjustable waistbands, and quick-drying fabrics make shorts more versatile. These details allow you to move easily from outdoor adventures to casual gatherings, keeping essentials close and ensuring comfort throughout the day.

Most men’s shorts are designed for easy care—machine washing with like colors and tumble drying on low will help preserve their shape and softness. Checking the care label for specific instructions is always a good idea, especially for blended or specialty fabrics.

Absolutely. Comfortable shorts are designed to transition seamlessly from active pursuits like hiking or cycling to laid-back settings such as backyard barbecues or relaxed evenings at home. Their timeless style and practical features make them a reliable choice for nearly any occasion.

Shorts make a thoughtful and practical gift because they offer comfort, versatility, and lasting value. Whether for a loved one who enjoys the outdoors or someone who appreciates easygoing everyday style, a well-chosen pair of shorts is sure to be appreciated and worn often.

It's time to upgrade your browser

Men's Comfortable Shorts

This product is not available