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      1. L.L.Bean/Tailored Men's Shirts
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      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
        Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
        $64.95
      • Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
        Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
        $64.95
      • Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
        Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
        $54.95
      • Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
        Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
        $69.95
      • Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
        Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
        $64.95
      • Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
        Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
        $69.95
      • Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
        Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
        $64.95
      • Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
        Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
        Price was from: $69.95 now: $54.99 $69.95 $54.99
      • Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
        Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
        $69.95
      • Men's Signature Microwale Corduroy Shirt
        Men's Signature Microwale Corduroy Shirt
        Price was from: $89 now: $64.99 $89 $64.99
      • Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
        Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
        Price was from: $89 now: $74.99 $89 $74.99
      • Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
        Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
        Price was from: $79 now: $64.99 $79 $64.99
      • Men's Signature Donegal Woven Shirt, Long-Sleeve
        Men's Signature Donegal Woven Shirt, Long-Sleeve
        $79
      • Men's Signature Vacationland Shirt, Short-Sleeve, Slim Fit
        Men's Signature Vacationland Shirt, Short-Sleeve, Slim Fit
        Price was from: $69.95 now: $49.99 $69.95 $49.99
      • Men's Scotch Plaid Flannel Shirt, Slightly Fitted
        Men's Scotch Plaid Flannel Shirt, Slightly Fitted
        $49.95
      • Men's Sunwashed Canvas Shirt, Traditional Fit
        Men's Sunwashed Canvas Shirt, Traditional Fit
        $64.95
      • Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
        Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
        $69.95
      • Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
        Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
        Price was from: $89 now: $69.99 $89 $69.99
      • Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
        Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
        $69.95
      • Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
        Men's BeanFlex® Twill Shirt, Traditional Untucked Fit, Long-Sleeve
        Price was from: $64.95 now: $54.99 $64.95 $54.99
      • Men's Signature 1933 Chamois Cloth Shirt, Slim Fit
        Men's Signature 1933 Chamois Cloth Shirt, Slim Fit
        $79
      • Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
        Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
        $59.95
      • Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
        Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
        Price was from: $69.95 now: $54.99 $69.95 $54.99
      • Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
        Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
        $79
      0 Items
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      • 2

      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.

      Popular Items

      Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
      Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
      $64.95
      Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
      Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
      $64.95
      Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
      Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
      $54.95
      Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
      Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
      $69.95
      Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
      Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
      $64.95
      Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
      Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
      $69.95
      Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
      Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
      $64.95
      Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
      Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
      $69.95
      Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
      Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
      $29.99 $69.95
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
      $69.95
      Men's Bean's Wrinkle-Free Everyday Shirt, Traditional Untucked Fit, Plaid, Long-Sleeve
      Men's Bean's Wrinkle-Free Everyday Shirt, Traditional Untucked Fit, Plaid, Long-Sleeve
      $49.99 $59.95
      Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit
      Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit
      $69.95
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
      $69.95
      Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Traditional Untucked Fit
      Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Traditional Untucked Fit
      $54.99 $69.95
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Short-Sleeve
      Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Short-Sleeve
      $59.95

      Related Pages

      • Women's Tailored Shirts
      • Men's Collared Shirts
      • Tailored Polos
      • Men's Dress Long Sleeve Shirts
      • Mens Easy Care Shirts
      • Male Casual Shirts
      • Work Shirts
      • Work Shirts For Men
      • Men's Embroidered Shirts
      • Men's Oxford Shirts
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