Broken In Shorts

Broken in shorts are your go-to choice for comfort and versatility, perfect for any outdoor adventure or casual day out. Designed with a lived-in feel right from the start, these shorts offer a relaxed and comfortable fit that you'll love wearing time and again. Whether you're hiking a scenic trail, enjoying a backyard barbecue, or simply running errands around town, broken in shorts provide the ideal blend of style and ease. Embrace the freedom to move effortlessly while enjoying the timeless appeal that makes these shorts a staple in any wardrobe.

Sort by:

Filter & Sort

388 Items

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

A pair of khaki cargo shorts made from 100% cotton with a 10" inseam and elastic side panels.

Pros: Lightweight fabric True to size Deep pockets Durable material Comfortable fit
Men's Tropic-Weight Cargo Shorts, Comfort Waist, 6"

A durable pair of brown cotton cargo shorts with a comfort waist and 6" inseam.

Pros: Lightweight fabric Versatile style Ample pockets Durable material Comfortable fit
Women's Comfort Stretch Shorts, Chino Bermudas 9" Print
Price was from: $69.95 now: $44.99

A pair of white printed cotton Bermuda shorts with stretch, featuring a soft feel and classic pockets.
Men's Sunwashed Khaki Shorts, 7"

A pair of green peached twill shorts offering lived-in softness and stretch for everyday 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.
Women's Comfort Stretch Shorts, Cargo 7"
Price was from: $69.95 now: $44.99

A pair of dusty olive, mid-rise cargo shorts made from a soft, stretchy cotton blend.
Women's Comfort Stretch Shorts, Chino Bermudas 9"
Price was from: $64.95 now: $44.99

A pair of tan stretch cotton Bermuda shorts with a 9" inseam and a comfortable mid-rise fit.
Women's 207 Vintage Cotton Canvas Shorts
Price was from: $59.95 now: $39.99

A pair of brown stretch canvas shorts offering lived-in softness and vintage style with utility pockets.
Men's BeanFlex® Corduroy Shorts, 7"
Price was from: $69.95 now: $34.99

A pair of cadet blue corduroy shorts with built-in stretch and a 7" inseam for comfort.
Men's Sunwashed Khaki Shorts, 9"

A pair of tan peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.
Men's Dock Shorts, 8"

A pair of walnut-colored, 100% organic cotton shorts with an 8" inseam and adjustable drawstring waist.

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

A pair of wrinkle-free khaki shorts with an 8" inseam and hidden elastic waist for comfort.

Pros: High quality Comfortable waistband Durable Good fit Wrinkle-free fabric
Men's Wrinkle-Free Double L® Chino Shorts, Classic Fit, 8"
Price was from: $54.95 now: $40.99

A pair of wrinkle-resistant khaki shorts with an 8" inseam, made from midweight 8.6 oz. cotton.

Pros: Great fit High quality Durable Comfortable Nice color
Women's Lakewashed Dock Shorts, Mid-Rise
Price was from: $49.95 now: $34.99

A pair of mid-rise, lightweight shorts in boulder, made from a soft organic cotton blend with stretch.

Pros: Well-made Durable Versatile Comfortable Consistent fit
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
Women's Lakewashed Dock Shorts, Mid-Rise Chambray

A pair of mid-rise chambray shorts in a soft-washed organic cotton blend with a drawstring elastic waist.

Pros: Great fit High-quality material Functional pockets Versatile style Exceptional comfort
Men's L.L.Bean Multisport Shorts, 7"

A rugged brown synthetic short with stretch, quick-dry comfort, UPF 50+ sun protection, and secure pockets.
Men's Signature Heritage Denim, Slim Fit
Price was from: $120 now: $99.99

A modern slim fit black denim with a hint of stretch for a comfortable, broken-in feel.
Men's Comfort Stretch Performance® Everywhere Chino Shorts, 8"
Price was from: $74.95 now: $49.99

A pair of brown chino shorts made from a soft, abrasion-resistant cotton-nylon blend with built-in stretch.
Men's Comfort Stretch Performance® Everywhere Chino Shorts, 6"

A pair of brown chino shorts made from a soft, lightweight cotton-nylon blend with built-in stretch.
Men's BeanFlex® Performance Canvas Shorts, 9"
Price was from: $74.95 now: $49.99

A rugged blue canvas short made from a soft, stretchable TENCEL cotton blend for everyday comfort.
Men's Field Chino Shorts, 7"
Price was from: $69.95 now: $44.99

A rugged pair of green cotton-blend chino shorts with stretch, abrasion resistance, and instant softness.
Women's Lakewashed Dock Shorts, Mid-Rise Embroidery
Price was from: $54.95 now: $34.99

A lightweight blue short made from organic cotton with stretch, embroidery, and a comfortable elastic waistband.
Women's Premium Washable Linen Shorts, Mid-Rise 6"
Price was from: $74 now: $36.99

A pair of blue, mid-rise linen shorts with a relaxed fit and adjustable drawcord waistband.

Broken In Shorts

There’s something special about slipping on a pair of broken in shorts—those favorites that feel like old friends from the first wear. The beauty of this style lies in its easygoing comfort and timeless appeal, making it a staple for anyone who values both relaxation and versatility in their warm-weather wardrobe. Broken in shorts are crafted to capture that lived-in softness, often achieved through special garment washing or finishing techniques that bring out the fabric’s best qualities. Whether you’re drawn to classic chino silhouettes, relaxed lounge fits, or even subtly distressed designs, these shorts are made for everyday ease. They’re the kind of shorts you reach for when heading out for a stroll with the dog, gathering with friends around the backyard fire pit, or packing for a weekend at the lake. For those who prefer a particular fit, options like llbean 6 inch shorts offer a tailored look that feels just right—not too long, not too short—striking the perfect balance between coverage and freedom of movement.

Broken in shorts make thoughtful gifts for anyone who loves the outdoors, appreciates classic style, or simply enjoys comfort that feels earned, not engineered. They’re a go-to choice for dads who want something easy and durable for yardwork, college students looking for casual campus attire, or anyone seeking an effortless piece for travel, hiking, or unwinding at home. The appeal extends across generations and lifestyles, making them a reliable pick for family vacations, afternoons spent exploring local trails, or just relaxing on the porch as the days grow longer. Because these shorts are designed to be worn again and again, they’re especially well-suited for those who value low-maintenance clothing that stands up to the rigors of everyday adventure. As the weather shifts from the height of summer into the early days of fall, broken in shorts remain a versatile option—pair them with tees on hot afternoons or layer with a favorite flannel as the air turns crisp.

When choosing broken in shorts, consider details like inseam length, pocket configuration, and overall fit to match your personal style and the activities you love. Some prefer the classic appeal of a chino short, while others gravitate toward more relaxed lounge styles or even cut-off looks for a bit of edge. The right pair should move with you and feel comfortable from the start, ready for impromptu games of catch, evenings by the water, or spontaneous road trips. If you’re exploring different lengths or styles, you might also enjoy browsing our selection of Short Shorts for even more ways to stay cool and comfortable as the seasons transition. No matter how you spend your time outside, a well-loved pair of broken in shorts brings together ease, versatility, and that unmistakable feeling of summer—making every moment just a little more memorable.

FAQs

Broken in shorts are designed to offer a soft, lived-in feel right from the start. They often feature pre-washed fabrics and thoughtful construction, so you get the comfort of your favorite well-worn pair without the wait. Their relaxed look and feel make them a go-to choice for casual outings, outdoor activities, and everyday wear.

Absolutely. Broken in shorts are crafted for durability and comfort, making them ideal for hikes, camping trips, and other outdoor adventures. Their easy movement and breathable fabrics help keep you comfortable whether you’re on the trail, at the campsite, or enjoying a day in the park.

While broken in shorts are known for their casual comfort, they’re also versatile enough to pair with a collared shirt or a lightweight sweater for a more put-together look. Their timeless style means they transition easily from backyard barbecues to casual dinners out.

Broken in shorts make a thoughtful gift for anyone who values comfort, practicality, and lasting quality. Outdoor enthusiasts, travelers, and those who enjoy relaxed weekends with family and friends will especially appreciate their easygoing style and versatility.

To maintain the softness and comfort of broken in shorts, wash them in cold water with like colors and tumble dry on low. Avoid using harsh detergents or bleach, as these can wear down the fabric over time. With proper care, your shorts will continue to feel great and look good season after season.

It's time to upgrade your browser

Broken In Shorts

Broken In Shorts

Popular Items

FAQs

Recommended

It's time to upgrade your browser

Broken In Shorts

Broken In Shorts

Popular Items

FAQs

Top Collections

Related Pages