Tailored Men's Shirts

Tailored men's shirts offer the perfect blend of style and comfort, making them an essential addition to any wardrobe. With their precise cuts and attention to detail, these shirts provide a polished look for both casual outings and formal events. Whether you're dressing up for a special occasion or looking for a versatile piece to elevate your everyday attire, tailored men's shirts deliver timeless appeal and lasting quality. Explore our collection to find the ideal shirt that complements your personal style and fits seamlessly into your lifestyle.

Sort by:

Filter & Sort

476 Items

Men's Signature 1933 Chamois Cloth Shirt, Slim Fit

A slim-fit gray heather flannel shirt made from 100% cotton, offering incomparable softness and comfort.

Pros: Perfect fit Quality Comfort Softness Style
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $79.95 now: $39.99

A lightweight chambray shirt in light mahogany, featuring quick-drying, moisture-wicking stretch fabric for ultimate comfort.
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A deep green, 100% cotton poplin shirt with wrinkle-free performance and moisture-wicking TrueCool® fabric.

Pros: Perfect fit Wrinkle-free Durable Comfortable Beautiful colors
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check

A nautical blue, wrinkle-free cotton sport shirt with moisture-wicking TrueCool® fabric and a relaxed traditional fit.

Pros: Great fit High quality Wrinkle-free Comfortable Nice color
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free white oxford shirt in 100% cotton with a traditional fit and durable buttons.

Pros: High quality Perfect fit Wrinkle-free Professional look Versatile
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
Price was from: $79.95 now: $67.99

A wrinkle-free, bright blue tattersall oxford shirt made from ultrasmooth 100% cotton for all-day comfort.

Pros: High quality Consistent sizing Wrinkle-free Durable Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check

A slightly fitted, wrinkle-free cotton sport shirt in blue check with moisture-wicking TrueCool® fabric.

Pros: Flattering fit Good quality Wrinkle-free Versatile style Comfortable
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A white, slightly fitted oxford shirt with moisture-wicking TrueCool® fabric and stretch for all-day comfort.

Pros: Good appearance High material quality Well-made Cute print Comfortable
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged cream twill flannel shirt with Donegal flecks, featuring a slim fit and button-down collar.
Men's Signature Vacationland Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $44.99

A slim-fit, 100% cotton camp shirt in Baltic Blue Animals, perfect for warm days and casual outings.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $39.99

A slim-fit, walnut-colored stretch poplin shirt made from a soft cotton blend with a button-down collar.
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
Price was from: $59.95 now: $49.99

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

Pros: Great fit High quality Softness Warmth Comfortable
Men's Sunwashed Canvas Shirt, Traditional Fit

A prewashed, 100% cotton canvas shirt in juniper with a relaxed fit and durable double-needle stitching.

Pros: High quality Durable Comfortable Good fit Nice color
Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve

A soft, green 100% cotton canvas shirt with a relaxed fit and durable double-needle stitching.

Pros: Versatile and stylish Perfect fit and true to size Durable and sturdy Soft and high-quality fabric Comfortable to wear
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $64.95 now: $54.99

A green plaid short-sleeve chambray shirt in a breathable, moisture-wicking cotton blend with added stretch.

Pros: Durable construction Attractive style and design Breathable, lightweight material Wrinkle-free fabric Comfortable fit
Men's Maine Guide Shirt with PrimaLoft

A warm, durable PrimaLoft wool blend shirt with sturdy seams and generous cuffs, ideal for layering.

Pros: Great fit Durable construction Excellent quality Warm and comfortable Stylish appearance
Men's Maine Guide Shirt

A durable, 85% wool, 15% nylon plaid shirt in cobalt or black, perfect for layering.

Pros: Great fit High quality Good quality Cushioning Warm
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 Brushed Jaspé Twill Shirt, Traditional Untucked Fit

A soft, lightweight brown cotton shirt with a textured look and relaxed untucked fit for year-round wear.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A pink plaid shirt with moisture-wicking stretch fabric, perfect for untucked wear and easy care.
Men's Stonecoast Hemp Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Stripe

A slightly fitted, untucked cotton blend shirt in silver birch with a stylish stripe pattern.
Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $44.99

A brown slim-fit short-sleeve shirt in soft, stretchy cotton blend, perfect for casual wear.
Men's Signature Seersucker Madras Shirt, Slightly Fitted, Short-Sleeve
Price was from: $69.95 now: $44.99

A breezy blue short-sleeve shirt in 100% cotton seersucker with a slightly fitted silhouette.
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.

Tailored Men's Shirts

When it comes to building a dependable wardrobe, tailored men’s shirts are a timeless staple that bring together comfort, versatility and a sense of easygoing style. Whether you’re heading into the office, gathering with friends for a backyard barbecue, or planning a weekend getaway, a well-chosen shirt can make all the difference. The beauty of a tailored shirt lies in its ability to offer a crisp, put-together look without ever feeling stuffy or restrictive. These shirts are thoughtfully designed with details that matter—like reinforced seams, quality buttons, and fabrics that feel soft against the skin but stand up to regular wear. In the warm days of late summer, breathable cottons and lightweight blends help keep you comfortable from morning meetings to evening strolls. As the season gradually shifts, these shirts layer effortlessly under sweaters or jackets, making them an ideal choice for unpredictable weather. Many folks find themselves reaching for these shirts again and again, not only because they look great, but because they’re built to last and adapt to whatever the day brings.

Tailored men’s shirts also make thoughtful gifts for birthdays, anniversaries, or any occasion that calls for something both practical and personal. They’re a welcome addition to any closet, appreciated by everyone from recent graduates stepping into their first job to longtime professionals who value lasting quality. The right shirt can help mark a milestone or simply brighten up an ordinary day. If you’re shopping for someone else, consider their favorite colors or patterns, and think about the activities they enjoy—maybe a classic plaid for weekend hikes, or a subtle solid for evenings out. These shirts are designed to move easily between settings, offering a sense of ease whether the wearer is hosting a family dinner, attending a special event, or just enjoying a quiet afternoon at home. For those moments that call for something a bit more refined, you can explore a wider range of options in our Mens Occasion Shirts collection, where you’ll find styles ready for every gathering on your calendar.

Choosing the right tailored shirt is about more than just appearance; it’s about finding a piece that fits seamlessly into your life. Look for features like easy-care fabrics that simplify your morning routine, or subtle touches like button-down collars and chest pockets that add both utility and character. The best shirts are the ones you reach for without thinking—the ones that feel just right, season after season. Whether you’re updating your own wardrobe or searching for a gift that’s sure to be appreciated, tailored men’s shirts offer lasting value, comfort, and a sense of everyday adventure. With the right shirt, you’re ready for anything the day might bring, from spontaneous road trips to relaxed evenings around the campfire.