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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298 Items

Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
Price was from: $64.95 now: $54.99
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $54.99
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
Price was from: $89 now: $74.99
Men's Signature Microwale Corduroy Shirt
Price was from: $89 now: $64.99
Men's Signature Vacationland Shirt, Short-Sleeve, Slim Fit
Price was from: $69.95 now: $49.99
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $64.99
Men's Signature Donegal Woven Shirt, Long-Sleeve
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
Men's Sunwashed Canvas Shirt, Traditional Fit
Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $69.99
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $54.99
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $54.99
Men's Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $64.99
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $79 now: $64.99

Tailored Men's Shirts

When you’re looking for a shirt that feels just right, a tailored men’s shirt stands out as a dependable choice in any wardrobe. There’s something special about slipping into a shirt that fits comfortably, looks sharp, and holds up through busy days and memorable evenings alike. Whether you’re heading to the office, getting together with friends for a weekend barbecue, or planning a special dinner out, a tailored shirt brings a sense of ease and confidence. The carefully considered details—like sturdy buttons, smooth seams, and a fit that moves with you—make all the difference. Think about those early spring mornings when a crisp shirt pairs perfectly with your favorite chinos, or the way a classic oxford feels under a lightweight jacket as the sun sets on a May evening. These shirts are designed for versatility, ready to take on everything from casual afternoons to important gatherings. For many, a tailored shirt is more than just a staple; it’s a reliable companion through seasons of change, offering comfort and timeless style that never feels out of place.

Tailored men’s shirts also make thoughtful gifts, especially as the calendar fills with celebrations and milestones. Graduation parties, Father’s Day, or simply saying thank you to someone special—these shirts are a practical and meaningful way to show you care. There’s a sense of pride in giving a shirt that’s built to last, knowing it will become part of someone’s favorite memories. The right shirt can turn an ordinary day into something worth remembering, whether it’s worn at a family reunion, a summer wedding, or a backyard cookout. With so many styles and colors to choose from, it’s easy to find something that matches the recipient’s personality and needs. And when the occasion calls for something a little more polished, you can always explore options specifically designed for special events, like those found on our Mens Occasion Shirts page. No matter how you wear or share them, tailored shirts are made to deliver lasting value, comfort, and a sense of belonging—season after season, year after year.