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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298 Items

Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A light cobalt, slightly fitted untucked oxford shirt with moisture-wicking cotton blend and stretch for comfort.

Pros: Good appearance High material quality Well-made Cute print Comfortable
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A blue cotton-blend chambray shirt with built-in stretch, moisture-wicking comfort, and a relaxed untucked fit.
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid

A bayside blue plaid oxford shirt with moisture-wicking, stretchable cotton blend, designed for untucked wear.

Pros: Lovely color High quality material Stylish Comfortable Good fit
Men's BeanFlex® Denim Shirt, Traditional Untucked Fit
Price was from: $64.95 now: $49.99

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® All-Season Flannel Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $49.99

A moisture-wicking, extra-soft flannel shirt in Maccallum, perfect for year-round wear and untucked style.

Pros: High quality Soft material Versatile design Vibrant colors Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $69.95 now: $59.99

A breathable orange chambray shirt with stretch, designed for comfort and style, perfect untucked.

Pros: Great fit High quality Attractive color Versatile style Excellent comfort
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $54.99

A wrinkle-free, ultrasoft brushed cotton shirt in soft spruce, designed for a slightly fitted untucked look.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable fabric Beautiful color
Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $54.99

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, Plaid

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 BeanBuilt Waffle Henley, Traditional Untucked Fit
Price was from: $64.95 now: $54.99

A durable cadet blue henley with a relaxed fit, made from 60% cotton and 40% polyester.

Pros: Great fit Perfect length Stylish look Cozy feel Excellent warmth
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $54.99

A light mahogany plaid oxford shirt with moisture-wicking, stretch cotton blend, designed for untucked wear.

Pros: High quality fabric Perfect fit Comfortable feel Wrinkle-free after washing Untucked design
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: $49.99

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, Short-Sleeve, Stripe

A breathable blue cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Traditional Untucked Fit
Price was from: $69.95 now: $29.99

A vintage indigo, wrinkle-free, ultrasoft brushed cotton shirt with a relaxed fit and shorter untucked hem.
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 Bean's Wrinkle-Free Everyday Shirt, Traditional Untucked Fit, Plaid, Short-Sleeve
Price was from: $54.95 now: $44.99

A breathable, no-iron cotton shirt in deep ocean plaid, designed for untucked wear with moisture-wicking fabric.

Pros: Repeat purchase Wrinkle-free Lightweight Nice for warm weather Great appearance
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe

A blue striped chambray shirt in a breathable cotton blend with stretch and moisture-wicking comfort.
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $59.99

A pink plaid chambray shirt with stretch, designed for comfort and style, perfect untucked.
Men's BeanFlex® Denim Shirt, Short-Sleeve, Traditional Untucked Fit
Price was from: $59.95 now: $49.99

A dark indigo short-sleeve denim shirt with built-in stretch, designed for untucked wear and all-day comfort.
Men's PrimaLoft Lined Chamois Shirt Jac, Traditional Untucked Fit, Stripe
Price was from: $129 now: $89.99

A heritage-inspired striped shirt jac with PrimaLoft insulation, made from heavyweight chamois flannel in barley multi.
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $59.95 now: $49.99

A versatile white plaid shirt with moisture-wicking stretch fabric, perfect for untucked wear.
Men's Backyard BBQ Shirt, Short-Sleeve, Traditional Untucked Fit, Plaid
Price was from: $59.95 now: $49.99

A lightweight, breathable plaid shirt in light gold with a relaxed untucked fit and built-in stretch.

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.