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.

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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 wrinkle-free, dark pine check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

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

A wrinkle-free white oxford shirt made from 100% cotton with a relaxed traditional fit.

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

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
Price was from: $69.95 now: $54.99

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

Pros: No ironing required Attractive color and style High-quality construction Wrinkle-free fabric Comfortable fit
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 Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $54.99

A slightly fitted plaid oxford shirt in soft juniper, made from a moisture-wicking cotton blend.

Pros: High quality fabric Perfect fit Comfort Wrinkle-free after washing Untucked design
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A white cotton-blend oxford shirt with moisture-wicking stretch fabric and a comfortable untucked fit.

Pros: High material quality Well-made construction Attractive appearance Comfortable fit
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
Price was from: $89 now: $74.99

A slim-fit oxford shirt in camp green plaid, crafted from 100% Pima cotton for luxurious softness.
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: $49.99

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: $64.99

A slim-fit, walnut-colored stretch poplin shirt made from a soft cotton blend with a button-down collar.
Men's Signature Seersucker Madras Shirt, Slightly Fitted, Short-Sleeve
Price was from: $69.95 now: $54.99

A green short-sleeve shirt in breathable cotton seersucker with a slightly fitted silhouette.
Men's Signature Microwale Corduroy Shirt
Price was from: $89 now: $64.99

A heritage-inspired mariner blue shirt made of 100% cotton microwale corduroy in a streamlined Slim Fit.
Men's Scotch Plaid Flannel Shirt, Slightly Fitted

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 Scotch Plaid Flannel Shirt, Slim Fit

A slim fit flannel shirt in antique dress stewart tartan, crafted from high-quality Portuguese cotton.

Pros: Rich colors and patterns Perfect fit Soft and comfortable High-quality cotton Warm and durable
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $59.99

A slim-fit, 100% cotton flannel shirt in faded black plaid, offering vintage softness and comfort.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid

A bayside blue plaid oxford shirt with moisture-wicking, stretchable cotton blend fabric for year-round comfort.

Pros: Lovely color High quality material Stylish Comfortable Good fit
Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $54.99

A rugged, midweight slub twill shirt in faded orange with built-in stretch for all-day comfort.

Pros: High quality Attractive color Wrinkle-free Durable material Comfortable fit
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® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid

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 Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $64.99

A soft, midweight cotton flannel shirt in American Khaki, featuring a slim fit and durable triple-needle stitching.

Pros: High quality Perfect fit Colorful True to size Versatile
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $79.95 now: $64.99

A rugged midweight flannel shirt in classic navy plaid, 100% cotton, with a slightly fitted untucked fit.

Pros: Great fit High-quality material Well-built design Very comfortable Excellent return policy

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.