Untucked Button Down Shirts

Untucked button down shirts bring a relaxed, timeless style to your everyday routine. Designed for easygoing comfort and effortless versatility, these shirts look just right whether you’re heading out for a weekend adventure or gathering with friends and family. With classic details and a laid-back silhouette, untucked button down shirts make it simple to enjoy lasting quality and all-day ease, wherever the day takes you.

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476 Items

Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

An indigo long-sleeve chambray shirt with built-in stretch, perfect for wearing untucked.

Pros: High quality Versatile design Soft fabric Good stretch Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
Price was from: $74.95 now: $59.99

A vintage indigo chambray shirt with built-in stretch, designed for comfort and moisture-wicking performance.

Pros: High quality Soft material True to size Comfortable Good stretch
Men's Riverton Ripstop Shirt, Long-Sleeve, Traditional Untucked Fit
Price was from: $79.95 now: $64.99

A green cotton-blend shirt featuring lightweight micro ripstop fabric, subtle texture, and a relaxed untucked fit.
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A light cobalt cotton blend shirt with moisture-wicking fabric and a relaxed, untucked fit.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A red cotton-blend oxford shirt with moisture-wicking stretch fabric and a comfortable untucked fit.

Pros: High material quality Well-made construction Attractive appearance Cute print Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A green plaid chambray shirt in a breathable cotton blend with stretch and a modern untucked fit.

Pros: Attractive colors Perfect fit Receives compliments Great looking style
Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit

A lightweight brown cotton shirt with a relaxed fit and richly textured jaspé yarns.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $64.95 now: $54.99

A breathable brown plaid chambray shirt in a cotton blend with stretch and a relaxed untucked fit.

Pros: Durable construction Stylish design Breathable material Wrinkle-free fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve

An indigo short-sleeve chambray shirt with moisture-wicking cotton blend and built-in stretch for comfort.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged midweight flannel shirt in barley plaid, 100% cotton, with a slightly fitted untucked fit.

Pros: Great fit High-quality material Well-built design Very comfortable Excellent return policy
Men's Bean's Wrinkle-Free Everyday Shirt, Traditional Untucked Fit, Plaid, Long-Sleeve
Price was from: $59.95 now: $39.99

A breathable, no-iron cotton poplin shirt in deep ocean plaid, designed for untucked wear.

Pros: Wrinkle-free Comfortable and durable Perfect for multiple seasons Wide size availability Bright and refreshing color
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
Price was from: $74.95 now: $62.99

A breathable blue cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.

Pros: Easy to care for Great fabric quality Breathable material Stylish appearance Comfortable fit
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit
Price was from: $79.95 now: $54.99

A rugged brown cotton flannel shirt with a soft brushed finish, durable stitching, and untucked fit.
Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit, Plaid

A lightweight red corduroy shirt with a vintage plaid look, washed for softness and all-season comfort.
Men's Tropicwear CoolPro Fishing Shirt, Long-Sleeve

A green nylon long-sleeve shirt offering UPF 50+ sun protection, cooling technology, and odor resistance.
Men's BeanFlex® Denim Shirt, Traditional Untucked Fit
Price was from: $64.95 now: $44.99

A dark indigo denim shirt with built-in stretch, designed for untucked wear and all-day comfort.

Pros: Excellent fabric quality Perfect fit Well-made Classic style High comfort
Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $44.99

A rugged toffee-colored shirt with a comfortable cotton blend and built-in stretch for easy movement.

Pros: High-quality material Attractive color Wrinkle-free Durable construction Comfortable fit
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe
Price was from: $64.95 now: $54.99

A breathable blue cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.

Pros: Breathable fabric Attractive appearance Relaxed untucked style Comfortable fit
Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit
Price was from: $89.95 now: $74.99

A rugged brown cotton flannel shirt with a cozy hood, zip front, and extra-soft brushed finish.
Men's Stonecoast Hemp Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $49.99

A rugged, breathable hemp/cotton blend shirt with a slightly fitted untucked fit and vintage-inspired patterns.
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $74.95 now: $49.99

A pale khaki chambray shirt with built-in stretch, moisture-wicking cotton blend, and untucked fit.
Men's Cloud Gauze Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $59.95 now: $49.99

A superlight orange plaid shirt in breathable crinkled cotton gauze with a relaxed, untucked fit.
Men's Bean's Moleskin Shirt, Slightly Fitted Untucked Fit, Print
Price was from: $89.95 now: $74.99

A wonderfully soft allspice camo moleskin shirt with a touch of stretch and heritage-inspired prints.
Men's Bean's Moleskin Shirt, Slightly Fitted Untucked Fit
Price was from: $89.95 now: $69.99

A wonderfully soft, deep woods green moleskin shirt with a slightly fitted untucked fit and durable stitching.

Untucked Button Down Shirts

There’s something timeless and easygoing about untucked button down shirts—an unmistakable sense of comfort that fits right into the rhythm of summer days and cool evenings. Whether you’re heading out for a backyard barbecue, meeting friends at a lakeside café, or simply enjoying a stroll through the park, these shirts strike that perfect balance between relaxed and put-together. The untucked style is designed with a slightly shorter hem, so it drapes just right—never too long, never too short—making it easy to throw on over your favorite shorts or chinos. It’s a style that’s as at home on a casual Friday at the office as it is layered over a tee for a weekend adventure. With so many patterns, colors, and fabrics to choose from, there’s an option for just about every personality and every occasion. Lightweight cotton and linen blends keep things breezy when the sun is high, while soft flannels and brushed twills are there when the evenings cool off, offering comfort that lasts through every season.

Untucked button down shirts are a thoughtful gift for anyone who appreciates versatile, easy-to-wear pieces—dads, brothers, partners, or friends who enjoy spending time outdoors or relaxing with family. They’re a staple in any wardrobe, perfect for those who value both comfort and lasting quality. These shirts are built to handle the day’s adventures, from impromptu games of catch to campfire gatherings, and they look just as good fresh out of the dryer as they do after a full day of activity. When choosing the right shirt, consider details like breathable fabrics, reinforced seams, and easy-care finishes that stand up to repeated washings without losing their shape or softness. Look for a relaxed fit for ultimate comfort, or explore more tailored options—like those found in our Mens Slim Fit Untucked Shirts collection—for a modern, streamlined silhouette that still feels casual and approachable.

The beauty of untucked button down shirts lies in their adaptability. They pair effortlessly with everything from jeans and sneakers to khakis and boat shoes, making them a go-to choice for travel, family gatherings, or just enjoying the great outdoors. With their classic good looks and durable construction, these shirts are designed to be worn and enjoyed for years to come. They’re easy to pack, quick to throw on, and always ready for whatever the day brings—whether that’s a spontaneous picnic, a sunset walk along the shore, or a relaxed dinner on the patio. No matter how you wear them, untucked button down shirts offer a sense of freedom and laid-back style that makes every day feel a little more comfortable, a little more memorable, and a lot more fun.