Men's Comfortable Button Down Shirts

Men's comfortable button down shirts are a timeless staple that bring together classic style and everyday versatility. Whether you're heading to the office, relaxing at home, or enjoying the outdoors, these shirts offer reliable comfort and easy-going appeal for any occasion. With a variety of colors, patterns, and sizes to choose from, it's simple to find the perfect fit for your personal style. Enjoy the lasting quality and effortless wear that make men's comfortable button down shirts a go-to favorite season after season.

Sort by:

Filter & Sort

476 Items

Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A white cotton-blend plaid oxford shirt with stretch, moisture-wicking fabric, and an untucked fit.

Pros: Great fit High quality fabric Fashionable untucked design Comfortable feel Wrinkle-free after washing
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 moisture-wicking, untucked design.

Pros: Easy care Perfect fit Stylish design Comfortable stretch Great fabric
Men's Scotch Plaid Flannel Shirt, Traditional Fit

A soft, durable flannel shirt in authentic Scottish tartan, made from high-quality Portuguese cotton.

Pros: Fits well Good quality Softness Warmth Comfortable
Men's Sunwashed Canvas Shirt, Traditional Fit

A prewashed 100% cotton canvas shirt in bay leaf, featuring a relaxed fit and durable double-needle stitching.

Pros: High quality Durable construction Versatile for spring and fall Great color options Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A blue check button-down shirt crafted from wrinkle-free, moisture-wicking 100% cotton poplin.

Pros: Excellent fit and sizing options Comfortable and soft material Wrinkle-free and easy care Classic style and versatile design High quality and durable
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free pinpoint oxford shirt in French blue, made from 100% cotton with a traditional fit.

Pros: High quality Easy care Perfect fit Wrinkle-free Versatile
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

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

Pros: High quality Wrinkle-free Easy to care for Durable Comfortable fit
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 Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve
Price was from: $59.95 now: $50.99

A soft, blue cotton canvas short-sleeve shirt with a relaxed fit and durable double-needle stitching.

Pros: Perfect fit Durable and sturdy Versatile style Comfortable to wear Soft fabric
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

An indigo chambray shirt with built-in stretch, moisture-wicking cotton blend, and a relaxed untucked fit.

Pros: High quality Versatile design Good color options Soft fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Price was from: $74.95 now: $54.99

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

Pros: Perfect weight and warmth High quality and well made Good fit and flattering drape Attractive color options Soft and comfortable fabric
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $64.95 now: $31.99

A breathable, moisture-wicking burnt sienna plaid shirt with built-in stretch and a relaxed untucked fit.

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

A green cotton-blend chambray shirt with built-in stretch and a relaxed untucked fit.
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 plaid shirt in deep ocean, made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Perfect fit Wrinkle-free Comfy and durable Perfect for multiple seasons Bright and refreshing color
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 Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A white cotton blend oxford 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® Oxford Shirt, Slightly Fitted Untucked Fit

A white cotton blend oxford shirt with moisture-wicking TrueCool® fabric and a slightly fitted untucked fit.

Pros: Good appearance High material quality Well-made Cute print Comfortable
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, designed for comfort and untucked style.

Pros: Great looking Attractive colors Perfect fit Receives compliments
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged cream twill flannel shirt with Donegal flecks, slim fit, and button-down collar.
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 Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
Price was from: $64.95 now: $54.99

A breathable tan short-sleeve shirt crafted from a soft, durable hemp-cotton blend with vintage-inspired patterns.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $74.95 now: $59.99

A slightly fitted chambray shirt in a quick-drying, moisture-wicking cotton blend, perfect for untucked wear.
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 trimmer waist.
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 Comfortable Button Down Shirts

There’s something timeless and reassuring about a good button down shirt—especially when comfort is built right in. For generations, men have reached for these shirts for everything from family gatherings and backyard barbecues to crisp fall walks and everyday errands. As the leaves turn and October’s cool air settles in, a comfortable button down becomes even more appealing, offering just the right balance of warmth and breathability. Whether layered over a favorite tee or worn beneath a sweater, these shirts adapt easily to changing temperatures and shifting plans, making them a true staple as summer gives way to autumn. The right shirt feels soft from the start, moves easily with you, and stands up to the kind of repeated wear that comes with being a go-to favorite. Details like double-stitched seams, carefully finished collars, and smooth, easy-to-care-for fabrics can make all the difference, especially when you’re looking for lasting value and versatility.

When choosing a comfortable button down shirt, consider how and where it will fit into your routine. Some men rely on them for casual Fridays at the office, while others appreciate them for weekend hikes or relaxed evenings by the fire. They’re a thoughtful gift for anyone who values both style and practicality—sons heading off to college, dads who appreciate a classic look, or friends who love to spend time outdoors but still want to look put together. The best button downs are made to move with you, whether you’re reaching for a mug on the top shelf or heading out for a spontaneous adventure. Easy-to-use features like wrinkle resistance and generous pockets add convenience, while timeless patterns and colors ensure they’ll look just as good next season as they do today. For those moments when you need something a bit more refined—think special dinners or important meetings—explore our collection of Men's Button Down Dress Shirts, crafted for comfort and lasting appeal.

A comfortable button down shirt is more than just a piece of clothing—it’s an invitation to make the most of every day, whether you’re enjoying the outdoors or relaxing at home. The right shirt helps you feel confident and at ease, no matter where the day takes you. With the crispness of autumn in the air and the promise of new adventures ahead, now is the perfect time to add a few reliable options to your closet. Look for shirts that offer durability, easy care, and a timeless sense of style, so you’re always ready for whatever comes your way—be it a spontaneous road trip, a family get-together, or simply a quiet afternoon spent outdoors.

FAQs

Men's comfortable button down shirts are often crafted from soft, breathable fabrics such as cotton, cotton blends, flannel, and lightweight linen. These materials are chosen for their ability to provide comfort throughout the day and adapt to different temperatures, making them ideal for year-round wear.

To keep your button down shirts looking and feeling their best, wash them in cold or warm water with like colors and use a gentle detergent. Avoid over-drying, and remove promptly from the dryer to minimize wrinkles. For shirts with special finishes or details, follow the care instructions on the label for best results.

Yes, button down shirts are excellent for layering, especially in cooler months like October. They can be worn over a t-shirt for added warmth or under sweaters, vests, and jackets for a classic, comfortable look that adapts easily to changing temperatures.

Button down shirts are versatile enough for a wide range of occasions. They work well for casual outings, family gatherings, relaxed office settings, and even more polished events when paired with dress pants or under a blazer. Their timeless appeal makes them a reliable choice for nearly any setting.

When selecting a button down shirt, consider patterns and colors that reflect your personality and fit seamlessly into your wardrobe. Classic plaids, solid hues, and subtle prints are all great options. Look for details like pocket styles, collar shapes, and fabric textures to find a shirt that feels uniquely yours.

It's time to upgrade your browser

Men's Comfortable Button Down Shirts