Stretch Summer Shorts

Stretch summer shorts are your go-to choice for warm-weather adventures, offering a blend of comfort and style that's perfect for any outdoor activity. Designed to move with you, these shorts provide the freedom and ease you need whether you're hiking a new trail, enjoying a family picnic, or simply relaxing in the backyard. With a variety of styles and colors available, there's a pair of stretch summer shorts to suit every taste and occasion. Embrace the season with versatile options that keep you looking great while feeling even better.

Sort by:

Filter & Sort

476 Items

Men's Lakewashed® Stretch Khaki Shorts, 9"
Price was from: $59.95 now: $44.99

A pair of khaki shorts in washed cotton twill with 2% spandex for added comfort and flexibility.

Pros: High quality Perfect fit Durable Comfortable Breathable
Women's Vista Camp Shorts
Price was from: $69.95 now: $49.99

A rugged, quick-drying brown short with UPF 50+ protection and a comfortable elastic waistband.

Pros: High quality fabric Lightweight and breathable Quick-drying material Flattering and stylish Comfortable fit
Women's Stretch Ripstop Pull-on Shorts
Price was from: $59.95 now: $44.99

A pair of carbon navy pull-on shorts with a soft-knit waistband, made from 98% cotton and 2% spandex.

Pros: Durable Deep pockets Comfortable Good fit Nice color
Women's Vista Camp Bermuda Shorts
Price was from: $69.95 now: $49.99

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

Pros: Versatile for activities Lightweight fabric Quick-drying material Deep zippered pockets Comfortable fit
Men's L.L.Bean Multisport Shorts, 9"

A pair of graphite synthetic shorts with UPF 50+, featuring stretch comfort and quick-dry performance.

Pros: Quick-dry fabric Lightweight shorts Great looks Versatile design Comfortable fit
Women's L.L.Bean Stretch UPF Shorts, 9"
Price was from: $59.95 now: $39.99

A blue polyester-blend board short offering UPF 50+ sun protection, stretch comfort, and quick-draining pockets.
Women's Lakewashed Dock Shorts, Mid-Rise

A pair of white mid-rise shorts in a soft cotton blend with added stretch and elastic waist.

Pros: Well-made Durable True to size Versatile Comfortable
Men's Tropicwear Shorts, 9"

A pair of frost gray, 9" nylon shorts with sun protection and a semi-elasticized waistband.

Pros: Great fit Stylish look Secure pockets Lightweight material Comfortable
Women's Lakewashed Dock Shorts, Mid-Rise Chambray
Price was from: $49.95 now: $36.99

A lightweight blue chambray short made from soft-washed organic cotton blend with a comfortable drawstring waist.
Women's Lakewashed Dock Shorts, Mid-Rise Stripe
Price was from: $54.95 now: $26.99

A comfortable, mid-rise striped short with stretch cotton blend and elastic waist for ultimate ease.

Pros: Perfect fit Suitable for steamy summers Versatile style Softness of the chambray pair Goes well with different colors
Men's L.L.Bean Multisport Shorts, 7"

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

Pros: Perfect fit Wrinkle resistance Comfortable material Deep pockets Lightweight design
Women's Tropicwear Shorts, Mid-Rise

A pair of mid-rise, quick-drying shorts in soft sand, made from 96% nylon and 4% spandex.

Pros: Great fit Lightweight Good pockets High quality workmanship Comfortable
Women's Tropicwear Comfort Shorts
Price was from: $64.95 now: $47.99

A pair of storm blue, mid-rise fishing shorts with UPF 50+ protection and a stretchy, fast-drying fabric.

Pros: Good inseam length Easy on and off Soft fabric
Women's Lakewashed Dock Shorts, Mid-Rise Embroidery
Price was from: $54.95 now: $39.99

A lightweight blue short made from soft, stretchy organic cotton with embroidery and an easy pull-on waist.
Men's Ripstop Hybrid Shorts, 7"
Price was from: $69.95 now: $34.99

A versatile pair of red shorts with UPF 50+ protection, perfect for swimming and everyday wear.
Men's VentureStretch Five-Pocket Shorts, 9"

A versatile blue short made from stretchy, abrasion-resistant nylon blend with UPF 50+ and water-repellent finish.
Women's Bean's Seacoast Seersucker Shorts
Price was from: $49.95 now: $36.99

A lightweight white seersucker short made from a soft cotton-modal blend with easy pull-on comfort.
Men's Field Chino Shorts, 7"

A rugged pair of gray cotton-blend chino shorts with stretch twill and garment-washed softness.
Men's Comfort Stretch® Chino Shorts, 8"

A pair of brown chino shorts with a breathable cotton/polyester blend and built-in stretch for comfort.
Women's Comfort Stretch Shorts, Cargo 7"
Price was from: $69.95 now: $49.99

A pair of dusty olive cargo shorts with a 7" inseam, made from a soft cotton-spandex blend.
Men's Everyday Poplin Shorts, Standard Fit, 8"
Price was from: $64.95 now: $47.99

A lightweight green cotton-blend short with built-in stretch, featuring an 8" inseam and standard fit.
Women's Comfort Stretch Shorts, Chino Bermudas 9" Print
Price was from: $69.95 now: $51.99

A pair of blue printed cotton twill Bermuda shorts with stretch, offering a soft, comfortable fit.
Women's Comfort Stretch Shorts, Chino Bermudas 9"
Price was from: $64.95 now: $47.99

A pair of green stretch cotton Bermuda shorts with a soft, broken-in feel and classic chino style.
Men's Sunwashed Khaki Shorts, 9"

A pair of tan peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.

Stretch Summer Shorts

When the days grow longer and the warmth of the sun calls us outdoors, comfortable stretch shorts become an essential part of everyday life. Whether you’re setting out for a family picnic, chasing kids through the yard, or heading off for a casual walk by the water, the right pair of shorts makes all the difference. Stretch summer shorts are thoughtfully designed to move with you, blending lightweight fabrics and a touch of stretch so you can bend, sit, and explore in total comfort. Many styles feature elastic waistbands, easy pull-on designs, and practical pockets—details that simplify busy mornings and keep you ready for whatever the day brings. From relaxed afternoons spent gardening to spontaneous games of catch at the park, these shorts are made for all the ways you connect with loved ones and soak up the restorative power of being outside.

Choosing the best pair of stretch summer shorts comes down to how you like to spend your time outdoors. For those who enjoy active pursuits—like hiking local trails, setting up camp, or paddling on calm lakes—look for shorts with quick-dry performance, moisture-wicking properties, and a bit of rugged durability. If your days are more about unwinding on the porch, running errands, or strolling through farmers’ markets, you’ll appreciate the timeless comfort of soft cotton blends and classic fits. These shorts are a thoughtful gift for anyone who values time outside, from the friend who loves a morning jog to the family member who prefers a quiet afternoon in the hammock. They’re also a great addition to travel wardrobes, offering easy care and versatility for road trips, camping adventures, or long weekends at the cabin. As you build your summer rotation, consider inseam lengths and fit preferences—some favor a tailored, above-the-knee look for a polished feel, while others opt for a longer, relaxed cut for extra coverage and ease. And for those who enjoy a bit of everything, styles that transition seamlessly from trail to town keep you prepared for whatever the day brings.

No matter how you enjoy the warmer seasons, comfortable stretch shorts are made to help you get the most out of every moment. With practical features, durable construction, and nature-inspired colors, they’re designed to stand up to countless washes and seasons of wear. If you’re looking for more options designed for adventure, be sure to explore our Stretch Spring Hiking Shorts for styles that offer even more versatility for active days. Whether you’re gifting a pair to someone special or refreshing your own wardrobe, these shorts are a reliable choice for anyone who loves to spend time outdoors—making it easy to move, play, and experience the shared joy of summer.