Large Dress Shirts

Explore the perfect blend of comfort and style with our collection of large dress shirts. Designed to offer a flattering fit while ensuring ease of movement, these shirts are ideal for any occasion, from a day at the office to an evening out. With a variety of colors and patterns to choose from, finding the right shirt to match your personal style has never been easier. Each piece is crafted with attention to detail, ensuring you feel confident and look sharp every time you step out.

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298 Items

Men's Chamois Shirt, Traditional Fit, Plaid

An extra-large, apple cinnamon plaid shirt made from 7.5 oz. Portuguese cotton flannel for exceptional warmth.

Pros: Great fit High quality Very comfortable Exceptional warmth Durable
Men's Chamois Shirt, Traditional Fit

A navy, heavyweight chamois flannel shirt, perfect as a light jacket or essential layering piece.

Pros: Nice colors Great quality Warmth Versatile use Comfortable fit
Men's Sunwashed Canvas Shirt, Traditional Fit

A cadet blue, 100% cotton canvas shirt with a relaxed fit and durable double-needle stitching.

Pros: High quality Durable Comfortable Good fit Nice color
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A green 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 wrinkle-free, 100% cotton check shirt in bering blue with moisture-wicking TrueCool® fabric and a relaxed fit.

Pros: Generous fit High quality Wrinkle-free Easy to wear Comfortable fabric
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free, 100% cotton shirt in French blue, offering a relaxed fit and ultrasmooth finish.

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 shirt in crystal blue tattersall with a traditional fit for all-day comfort.

Pros: High quality Wrinkle-free Easy to care for Durable Comfortable fit
Men's Tropics Shirt, Short-Sleeve Print

A green, 100% cotton tropical shirt with a relaxed fit and weathered look for ultimate comfort.

Pros: Great color and pattern Durable quality Versatile style Cool and lightweight Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $69.95 now: $44.99

A green check button-down shirt in wrinkle-free cotton poplin with moisture-wicking TrueCool® technology.

Pros: Attractive color and design Versatile style High quality construction Wrinkle-free fabric Comfortable fit
Men's Katahdin Performance Flannel Shirt, Slightly Fitted
Price was from: $99.95 now: $49.99

A slightly fitted, quick-drying flannel shirt in evening blue or shadow green, made from a polyester/wool blend.

Pros: Comfort Warmth Durable Stylishness Versatility
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $44.99

A vintage indigo, wrinkle-free, 100% brushed cotton shirt with a slightly fitted untucked fit.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid

A bayside blue plaid oxford shirt with moisture-wicking, stretchable cotton blend, designed for untucked wear.

Pros: Lovely color High quality material Stylish Comfortable Good fit
Men's Tropicwear Shirt, Long-Sleeve

A blue long-sleeve shirt with UPF 50+ protection, built-in stretch, and wrinkle-free fabric.

Pros: Lightweight fabric Effective sun protection High quality Versatile design Comfortable fit
Men's Chamois Shirt, Slightly Fitted, Plaid
Price was from: $84.95 now: $54.99

A slightly fitted, extra-large men's shirt in barley plaid, made from 7.5 oz. Portuguese cotton flannel.

Pros: Perfect fit Excellent quality Warmth Comfortable Versatility
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid

A green plaid short-sleeve shirt in a breathable cotton blend with stretch and moisture-wicking comfort.

Pros: Attractive style Durable construction Breathable material Wrinkle-free fabric Comfortable fit
Men's Chamois Shirt, Slightly Fitted

A navy, extra-large, slightly fitted shirt made from 7.5 oz. Portuguese cotton flannel for exceptional warmth.

Pros: Well-constructed seams Exceptional warmth Softness High-quality fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $44.99

A blue cotton-blend plaid shirt with stretch, moisture-wicking performance, and an untucked, slightly fitted design.

Pros: High quality fabric Perfect fit Attractive untucked design Comfortable feel Wrinkle-free after washing
Men's Chamois Shirt, Traditional Fit, Stripe
Price was from: $74.95 now: $49.99

A navy, extra-large chamois shirt made from 7.5 oz. Portuguese cotton flannel, perfect for layering.

Pros: Perfect for colder weather Unique colors Well made Soft fabric Generous sizing
Men's Maine Guide Shirt

A durable, 85% wool and 15% nylon plaid shirt, perfect for layering and outdoor adventures.

Pros: Great fit High quality Good quality Cushioning Warm
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A light cobalt cotton blend shirt with moisture-wicking and stretch, designed for untucked wear.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A light cobalt cotton blend oxford shirt with moisture-wicking TrueCool® fabric and a slightly fitted untucked fit.

Pros: High material quality Well-made Cute print Great appearance Comfortable
Men's Lakewashed Twill Shirt, Traditional Untucked Fit
Price was from: $69.95 now: $44.99

A casual deep olive shirt in a soft cotton/TENCEL blend, perfect for warm weather and untucked wear.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Print

A blue cotton-blend shirt featuring moisture-wicking stretch fabric and a slightly fitted untucked design.
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
Price was from: $59.95 now: $44.99

A green cotton blend shirt with moisture-wicking fabric, designed for comfort and untucked wear.

Large Dress Shirts

When it comes to finding the right large dress shirt, comfort and confidence go hand in hand. A well-made dress shirt is more than just a wardrobe staple—it’s a reliable companion for busy workdays, family gatherings, weekend celebrations, and everything in between. The best large dress shirts are thoughtfully designed with generous proportions to ensure ease of movement, whether you’re reaching for a handshake at a meeting or rolling up your sleeves at a backyard barbecue. Details like reinforced seams, sturdy buttons, and soft yet durable fabrics make all the difference, allowing you to focus on the moment instead of fussing with your clothes. For those who spend long hours in the office or on the go, features like wrinkle resistance and breathable cotton blends are especially valuable, keeping you looking sharp from morning coffee through late-night dinners. In the warm days of July, lightweight dress shirts in large sizes offer welcome relief, pairing easily with khakis or shorts for a look that’s as comfortable as it is timeless.

Large dress shirts also make thoughtful gifts for birthdays, graduations, or Father’s Day—occasions when you want to give something practical but still personal. A classic dress shirt in a roomy fit is a gift that keeps on giving, ready to be dressed up with a tie for special events or worn open-collar for a more relaxed outing. For anyone who appreciates lasting value, these shirts stand up to countless washes and wears, making them a favorite season after season. They’re a smart choice for travelers, too, thanks to their versatility—easily transitioning from a day of sightseeing to a dinner reservation without missing a beat. And if you’re shopping for someone who enjoys a bit of variety, consider the wide range of styles, colors, and patterns available, each offering its own distinctive character. For women seeking the same level of comfort and quality, explore our collection of Women's Dress Shirts, thoughtfully designed to deliver the same reliable fit and enduring style.

No matter where your day takes you, the right large dress shirt helps you feel prepared for anything—whether you’re heading into an important presentation, catching up with friends at a summer picnic, or simply enjoying a quiet evening outdoors. These shirts are crafted to stand up to real life, with practical details and classic style that never feels out of place. With a focus on quality materials and expert construction, they’re built to last and easy to care for, making them a dependable part of your wardrobe for years to come. As you browse the selection, think about the moments that matter most to you and choose a shirt that fits not just your body, but your lifestyle—ready for every adventure, big or small.

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Large Dress Shirts