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, Short-Sleeve

An indigo short-sleeve chambray shirt with moisture-wicking cotton blend and built-in stretch for comfort.
Men's BeanFlex® Denim Shirt, Traditional Untucked Fit
Price was from: $64.95 now: $31.99

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 Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A versatile white oxford shirt with moisture-wicking cotton blend and stretch for ease of movement.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Print

A rugged, breathable short-sleeve shirt in a hemp/cotton blend with vintage-inspired patterns and a trimmer waist.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $59.95 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, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A vintage indigo plaid chambray shirt with built-in stretch, perfect for wearing untucked.

Pros: Great looking Attractive colors Perfect fit Receives compliments
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.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $69.95 now: $59.99

An orange cotton blend shirt with built-in stretch, perfect for wearing untucked with ease.

Pros: High quality Attractive color Versatile design Soft fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A gray cotton-blend chambray shirt with built-in stretch, moisture-wicking fabric, and a relaxed untucked fit.
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $34.99

A vintage indigo, wrinkle-free, 100% brushed cotton shirt with a slightly fitted untucked fit.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A deep green plaid oxford shirt with moisture-wicking cotton blend and a slightly fitted untucked fit.

Pros: High quality fabric Perfect fit Comfortable feel Wrinkle-free after washing Untucked design
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 Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe

A breathable red cotton-blend chambray shirt with stretch, moisture-wicking fabric, and a relaxed untucked fit.
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
Price was from: $74.95 now: $62.99

A blue striped chambray shirt in a breathable cotton blend with stretch and moisture-wicking comfort.

Pros: Easy to care for Stylish design Breathable and stretchy Great fabric quality Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A versatile white oxford shirt with moisture-wicking TrueCool® fabric, designed for untucked wear and easy care.

Pros: Good appearance High material quality Well-made Cute print Comfortable
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 Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Stripe

A rugged gray short-sleeve shirt in a soft, breathable hemp/cotton blend with a slightly fitted untucked fit.
Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid

A vintage indigo plaid chambray shirt with built-in stretch, designed for comfort and untucked wear.
Men's Lakewashed Performance Polo, Short-Sleeve
Price was from: $49.95 now: $24.99

A classic navy short-sleeve polo with moisture-wicking, UPF 50+ fabric, and resilient stretch for comfort.
Men's Lakewashed Twill Shirt, Traditional Untucked Fit
Price was from: $69.95 now: $34.99

A bright blue cotton/TENCEL blend shirt with a relaxed fit and built-in stretch for easy movement.
Men's Riverton Ripstop Shirt, Short-Sleeve, Traditional Untucked Fit
Price was from: $64.95 now: $54.99

A lightweight tan shirt in soft micro ripstop cotton blend, perfect for untucked, relaxed wear.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $54.99

A slim-fit, mineral red shirt made from a soft cotton blend, perfect for casual, untucked wear.
Men's Comfort Stretch Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Stripe
Price was from: $69.95 now: $29.99

A dark indigo striped chambray shirt with built-in stretch, designed for comfort and versatility.
Men's BeanFlex® Denim Shirt, Slightly Fitted Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $19.99

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

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.