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
Price was from: $69.95 now: $58.99

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

Pros: Lightweight and breathable fabric Attractive classic design Wrinkle-free and easy care High quality and durable Comfortable fit
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, 100% cotton shirt in French blue with a traditional fit and durable, non-iron fabric.

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 Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check

A wrinkle-free, slightly fitted check shirt in Bering Blue, made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Attractive color High-quality construction Wrinkle-free fabric Comfortable fit No ironing needed
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $44.99

An arctic blue, wrinkle-free, brushed cotton shirt with a slightly fitted untucked fit for ultimate comfort.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color
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 Vacationland Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $34.99

A slim-fit, 100% cotton camp shirt in Baltic Blue Animals, perfect for warm days and casual outings.
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 Comfort Stretch Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
Price was from: $74.95 now: $62.99

A blue striped cotton-blend oxford shirt with stretch, moisture-wicking performance, and an untucked fit.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $38.99

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: $44.99

A breezy red short-sleeve shirt made from 100% cotton seersucker with a slightly fitted design.
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
Price was from: $89 now: $74.99

A slim-fit oxford shirt crafted from 100% Pima cotton for exceptional softness and year-round comfort.
Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit

A brown cotton-blend chambray shirt with moisture-wicking, quick-drying stretch and a slightly fitted untucked fit.
Men's Signature Wharfside Linen Blend Shirt

A breathable tan linen-cotton blend shirt with a slim fit, button-down collar, and chest pocket.
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
Price was from: $59.95 now: $49.99

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

Pros: High quality Perfect fit Softness Warmth Comfortable
Men's Scotch Plaid Flannel Shirt, Slim Fit
Price was from: $59.95 now: $44.99

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

Pros: Perfect fit Soft and comfortable High-quality cotton Stylish appearance Warm and durable
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 Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $75.99

A slim-fit brown plaid flannel shirt crafted from soft Portuguese cotton for a vintage, broken-in feel.
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 built-in stretch, perfect for untucked wear and easy movement.

Pros: Great fit High quality Attractive color Versatile design Excellent comfort
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged white cotton flannel shirt with a soft brushed finish and durable triple-needle stitching.
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 Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe

A breathable red cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.

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.