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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476 Items

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 Classic Oxford Cloth Shirt, Traditional Fit

A wrinkle-free white oxford shirt with a traditional fit, crafted from 100% cotton for ultimate comfort.

Pros: Great fit High quality Wrinkle-free Versatile Comfortable
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
Price was from: $59.95 now: $50.99

A wrinkle-free, moisture-wicking cotton shirt in lake check with a relaxed traditional fit and buttoned collar.

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 made from 100% cotton with a relaxed traditional fit.

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

A wrinkle-free, 100% cotton oxford shirt with a traditional fit and stylish French blue university stripes.

Pros: High quality Perfect fit Wrinkle-free Classic style Comfortable
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
Price was from: $69.95 now: $44.99

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: $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 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 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 Wharfside Linen Blend Shirt

A breathable green linen-cotton blend shirt with a slim fit, button-down collar, and chest pocket.
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 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 all-season comfort.
Men's Signature Vacationland Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $34.99

A green slim-fit cotton shirt with a spread collar and buttoned front pocket, perfect for warm days.
Men's Wrinkle-Free Kennebunk Sport Shirt, Long-Sleeve, Slim Fit, Check

A green slim-fit cotton poplin shirt offering wrinkle-free performance and moisture-wicking comfort.
Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $44.99

A blue slim-fit short-sleeve shirt made from a soft cotton blend with a button-down collar.
Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit

A lightweight, deep blue heather cotton shirt with a relaxed fit and brushed for extra softness.
Men's Scotch Plaid Flannel Shirt, Slightly Fitted

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

Pros: Quality construction Perfect fit Softness Warmth Vibrant colors
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 tartan, made from high-quality Portuguese cotton.

Pros: Rich colors Perfect fit Soft and comfortable Stylish design High-quality cotton
Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve

A soft, prewashed green cotton canvas shirt with durable stitching and a relaxed traditional fit.

Pros: Perfect fit Soft material Durable fabric Versatile style 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 vintage-inspired comfort and style.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

A green cotton blend shirt with built-in stretch and a shorter hem for untucked wear.

Pros: High quality Attractive color Versatile design Soft fabric Comfortable fit
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $79.95 now: $67.99

A rugged white cotton flannel shirt with a soft brushed finish and durable triple-needle stitching.

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.