Smart Casual Shorts

Smart casual shorts make it easy to enjoy comfort and versatility, whether you're heading out for a relaxed afternoon or gathering with friends. Designed for everyday ease, these shorts combine timeless style with practical details, so you can look and feel great wherever the day takes you. With classic colors and thoughtful touches, smart casual shorts are ready for everything from backyard barbecues to weekend getaways.

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298 Items

Men's Lakewashed® Stretch Khaki Shorts, 9"

A pair of navy khaki shorts with 9" inseam, made from 98% cotton and 2% spandex.

Pros: High quality Durable Comfortable Good fit Breathable
Men's Dock Shorts, 8"

A pair of 8" walnut shorts made from 100% organic cotton twill with a comfortable drawstring waist.

Pros: High quality Lightweight 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 hidden elastic waist, made from premium 100% cotton.

Pros: High quality Durable Good fit Comfortable waist Wrinkle-free fabric
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 heritage khaki pull-on shorts with an 8" inseam, made from 98% cotton and 2% spandex.

Pros: Perfect fit Softness Durable Versatile Comfortable
Men's Tropicwear Shorts, 9"
Price was from: $64.95 now: $54.99

A redesigned favorite, these dark cinder nylon shorts offer sun protection, comfort, and multiple pockets.

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 pair of alloy gray ripstop shorts with an 8" inseam, featuring a moisture-wicking polyester blend.

Pros: Great fit Neat and trim appearance Durability Well put together Comfortable
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
Men's Tropicwear Comfort Shorts, 8"

A lightweight, tan short made from recycled polyester blend with UPF 50+ sun protection and water-repellent finish.
Men's Lakewashed® Stretch Khaki Shorts, 6"

A comfortable pair of tan khaki shorts in a cotton blend with a 6" inseam and stretch.
Men's VentureStretch Chino Shorts, 7"

A versatile blue short with a 7" inseam, featuring water-resistant nylon blend and UPF 50+ protection.
Men's BeanFlex® Corduroy Shorts, 7"
Price was from: $69.95 now: $59.99

A pair of dune brown corduroy shorts with 7" inseam, offering stretch comfort and broken-in softness.
Men's Comfort Stretch® Chino Shorts, 8"

A breathable cotton/CoolMax blend short with built-in stretch, moisture-wicking, and an 8" inseam.
Men's Signature Herringbone Shorts, 8"
Price was from: $79 now: $64.99

A versatile tan short in a breathable linen/cotton blend with stylish herringbone texture and utility details.
Men's Everyday Poplin Shorts, Standard Fit, 8"

A lightweight gray cotton-blend short with built-in stretch, featuring an 8" inseam and standard fit.
Men's Wide-Wale Cord Pull-On Shorts, 7"

A pair of tan cotton-blend corduroy shorts featuring wide wales, elastic waist, and all-day 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 Ripstop Hybrid Shorts, 7"
Price was from: $69.95 now: $54.99

A versatile blue short with UPF 50+, made from recycled nylon blend, perfect for swimming or casual wear.
Men's Sunwashed Cotton Shorts, 8"
Price was from: $59.95 now: $44.99

A pair of shale gray cotton blend shorts with an elastic waist and 8" inseam for ultimate comfort.

Smart Casual Shorts

Smart casual shorts are a reliable choice for anyone looking to strike the perfect balance between relaxed comfort and polished style during the warmer months. Whether you’re heading to a backyard gathering, enjoying a casual Friday at the office, or strolling through a coastal town on a summer getaway, these shorts offer a versatile foundation for a variety of occasions. The key lies in the details—think crisp, tailored lines, sturdy stitching, and a fit that sits comfortably just above the knee. Lightweight fabrics like linen and cotton blends are especially popular this time of year, providing the breathability you need to stay cool when August afternoons turn balmy. It’s easy to appreciate the difference these materials make, especially when you’re spending long hours outdoors or moving from sun-drenched patios to shaded porches. Choosing shorts in classic, neutral colors—such as khaki, navy, or light gray—makes pairing with polos, button-downs, or breezy tees a breeze, ensuring you always look put-together without any fuss.

Gifting smart casual shorts can be a thoughtful gesture for birthdays, graduations, or simply as a way to help someone refresh their summer wardrobe. They’re a practical yet appreciated present for college students, busy parents, or anyone who values clothing that transitions effortlessly from day to night. Picture an easy weekend morning: you slip into a pair of tailored shorts, add a crisp shirt, and you’re ready for coffee runs, errands, or impromptu gatherings with friends. Later, swap out sneakers for loafers and you’re set for a dinner on the patio. The versatility and timeless appeal of smart casual shorts mean they’re often the first thing reached for when the dress code calls for something comfortable, yet a step above the everyday. For those who appreciate lasting value, look for features like reinforced seams, sturdy pockets, and easy-care fabrics that hold up to frequent wear and washing—details that make a real difference after a season’s worth of adventures.

When building a wardrobe for summer, it’s worth considering how smart casual shorts can be mixed and matched with your favorite tops and footwear. Their adaptability makes them a staple for travel, outdoor events, or simply enjoying downtime at home. With a focus on quality construction and classic style, these shorts are designed to serve you well year after year, never going out of style or feeling out of place. For even more options, including an expanded selection of styles and lengths, you can explore our full range of Casual Shorts to find the perfect pair for any occasion. Whether you’re dressing for comfort or aiming for a more refined look, smart casual shorts are a dependable choice for making the most of the season’s sunshine and easygoing moments.

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Smart Casual Shorts