Men's Stretch Button Down Shirts

Men's stretch button down shirts are the perfect blend of comfort and versatility, making them an essential addition to any wardrobe. These shirts offer a timeless style that seamlessly transitions from casual outings to more polished occasions. Whether you're heading to the office or enjoying a weekend adventure, the ease of movement and classic appeal of these shirts ensure you look and feel your best. Crafted with attention to detail and quality materials, men's stretch button down shirts provide lasting value for every moment of your day.

Sort by:

Filter & Sort

298 Items

Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

A wrinkle-free, 100% cotton shirt in crystal blue tattersall with a traditional, relaxed fit.

Pros: High quality Perfect fit Wrinkle-free Comfort Durability
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid

A slightly fitted, untucked plaid shirt in bayside blue, made from a moisture-wicking cotton blend.

Pros: High quality fabric Perfect fit Comfort Wrinkle-free after washing Untucked design
Men's VentureStretch Woven Shirt
Price was from: $79 now: $64.99

A durable, moisture-wicking stretch ripstop shirt with adjustable cuffs and two mesh-lined chest pockets.
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 Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $64.95 now: $54.99

A green check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Attractive color and style Versatile and flattering design High-quality construction Wrinkle-free fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

A breathable indigo chambray shirt with built-in stretch, designed for comfort and versatility.

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

A brown chambray shirt with moisture-wicking cotton blend and stretch for comfort, perfect untucked.

Pros: High quality material Well made Good stretch Soft fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Price was from: $69.95 now: $54.99

A yellow cotton-blend plaid shirt with stretch, moisture-wicking performance, and a relaxed untucked fit.

Pros: Well-made and durable High quality material Stylish design Attractive color and print Comfortable fit
Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $54.99

A sage cotton-blend twill shirt with built-in stretch, moisture-wicking, and a relaxed untucked fit.

Pros: High quality Wrinkle-free Well-made Great color Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid

A green plaid chambray shirt with built-in stretch and moisture-wicking cotton blend for ultimate comfort.

Pros: High quality Perfect fit Wrinkle-free Stylish design Durable
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve

A breathable indigo chambray shirt with built-in stretch, designed for comfort and untucked style.
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe

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

A light cobalt cotton blend shirt with moisture-wicking and stretch, designed for untucked wear.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
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® 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 Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A green plaid chambray shirt in a breathable cotton blend with stretch and a modern untucked fit.
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $59.99

A pale khaki chambray shirt with built-in stretch, moisture-wicking cotton blend, and untucked fit.
Men's Comfort Stretch® Corduroy Shirt, Long-Sleeve, Traditional Untucked Fit
Price was from: $69.95 now: $59.99

A casual corduroy shirt in coal with added stretch for comfort and a relaxed untucked fit.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $59.99

A green chambray shirt offering moisture-wicking comfort with a slightly fitted untucked fit for versatility.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $39.99

An emerald spruce slim fit shirt made from a soft, stretchy cotton blend, perfect for casual wear.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Print

A blue cotton blend shirt with moisture-wicking stretch fabric and a slightly fitted untucked design.
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 Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $54.99

A slim-fit green shirt in a soft cotton blend, perfect untucked for casual wear.
Men's BeanFlex® Denim Shirt, Slightly Fitted Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $29.99

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

Men's Stretch Button Down Shirts

When it comes to building a wardrobe that keeps up with everything on your calendar, men’s stretch button down shirts are a true staple that never lets you down. These shirts are thoughtfully designed for the man who values comfort just as much as classic style, whether he’s heading into the office, setting out on a weekend adventure, or simply enjoying a backyard barbecue with friends and family. The subtle stretch in the fabric moves easily with you, making these shirts a smart choice for days filled with activity—think of reaching up to grab a suitcase from the overhead bin, casting a line from the dock, or lending a hand with the grill at a summer cookout. The versatility of a stretch button down means you can count on it for everything from casual Friday meetings to spontaneous road trips, always looking put-together without sacrificing ease of movement or all-day comfort.

These shirts make a thoughtful gift for graduates stepping into their first job, dads who appreciate practical style, or anyone who enjoys the timeless look of a button down but wants a little more flexibility in their day. The range of patterns and colors ensures there’s something to suit every personality and occasion, from subtle checks and stripes to solid hues that pair effortlessly with jeans, chinos, or shorts. Durability is built right in, so you can expect these shirts to hold up season after season—whether they’re being packed for summer travel, layered under a sweater on cool evenings, or worn solo on sun-filled afternoons. Breathable fabrics help keep you cool and comfortable, especially during the warmer months, while easy-care features mean you can spend less time worrying about wrinkles and more time enjoying the outdoors.

As you browse this collection, you’ll notice that stretch button down shirts are a practical investment for anyone who values lasting value and timeless appeal. They transition seamlessly from one activity to the next, making them a go-to choice for busy days and laid-back moments alike. If you’re looking to expand your options for work or special occasions, be sure to explore our full range of Men's Button Down Dress Shirts. With so many ways to wear and enjoy them, stretch button downs have earned their place as a trusted favorite in any man’s closet—always ready for whatever the day brings, and always up for a little adventure.