Men's Check Shirts

Men's check shirts are a timeless staple in any wardrobe, offering a versatile and comfortable style that suits a variety of occasions. Whether you're heading out for a weekend adventure or need something polished for casual Fridays at the office, these shirts provide the perfect blend of durability and classic appeal. Available in an array of colors and patterns, men's check shirts are designed to keep you looking sharp and feeling great, no matter where your day takes you.

Sort by:

Filter & Sort

476 Items

Men's Scotch Plaid Flannel Shirt, Traditional Fit
Price was from: $59.95 now: $44.99

A soft, durable flannel shirt in authentic Scottish tartan, made from high-quality Portuguese cotton.

Pros: Fits well Good quality Softness Warmth Comfortable
Men's Chamois Shirt, Traditional Fit, Plaid
Price was from: $84.95 now: $41.99

A heavy-weight, ultra-soft plaid flannel shirt in barley, perfect for layering with a relaxed traditional fit.

Pros: High quality Attractive color Softness Warmth Comfortable fit
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A deep sapphire multi houndstooth flannel shirt offering superior softness, warmth, and resistance to shrinking and wrinkling.

Pros: Great quality Warmth Excellent fit Comfortable Superior softness
Men's Scotch Plaid Flannel Shirt, Slightly Fitted

A slightly fitted indigo tartan flannel shirt made from 100% Portuguese cotton for lasting comfort.

Pros: Great fit High quality Softness Warmth Comfortable
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Price was from: $69.95 now: $58.99

A wrinkle-free deep green check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Fits well Wrinkle-free Durable Comfortable Beautiful colors
Men's Fleece-Lined Flannel Shirt, Traditional Fit

A supersoft black plum plaid flannel shirt with cozy polyester fleece lining and a relaxed traditional fit.

Pros: Quality Comfort Warmth Softness Versatility
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check

A blue check short-sleeve shirt made from wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe

A wrinkle-free cotton oxford shirt in French blue stripes, offering a traditional fit and classic tailoring.

Pros: High quality Perfect fit Wrinkle-free Classic style Comfortable
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
Price was from: $79.95 now: $67.99

A wrinkle-free, bright blue tattersall shirt made from ultrasmooth 100% cotton for all-day comfort.

Pros: High quality Perfect fit Wrinkle-free Durable Comfortable
Men's Scotch Plaid Flannel Shirt, Slim Fit

A slim-fit flannel shirt in Grey Stewart tartan, made from high-quality Portuguese cotton.

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

A slim-fit green plaid flannel shirt crafted from soft, vintage-washed Portuguese cotton for lasting comfort.

Pros: Warm and heavyweight material Soft and comfortable fabric Flattering slim fit Attractive color and pattern High quality construction
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
Price was from: $74.95 now: $59.99

A pink chambray shirt with built-in stretch, moisture-wicking cotton blend, and a relaxed untucked fit.

Pros: High quality Soft material True to size Comfortable Good stretch
Men's Chamois Shirt, Slightly Fitted, Plaid
Price was from: $84.95 now: $41.99

A forest shade, slightly fitted flannel shirt made from 7.5 oz. Portuguese cotton for exceptional warmth.

Pros: Perfect fit Exceptional warmth Comfortable wear Excellent quality Versatile use
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $59.95 now: $50.99

A pink plaid chambray shirt with stretch, moisture-wicking cotton blend, designed for untucked wear.

Pros: High quality Perfect fit Wrinkle-free Stylish design Durable
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve

A breathable green cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $79.95 now: $67.99

A rugged midweight flannel shirt in barley plaid, made from 100% cotton with a slightly fitted untucked fit.

Pros: Great fit High-quality material Well-built Very comfortable Excellent return policy
Men's Maine Guide Shirt with PrimaLoft

A warm, durable wool-blend shirt with PrimaLoft, featuring a relaxed fit and check pattern in red and black.

Pros: Great fit Excellent quality Warmth Durable Comfortable
Men's Maine Guide Shirt

A durable, plaid field guide shirt in red and black, made from an 85% wool and 15% nylon blend.

Pros: Great fit High quality Good quality Cushioning Warm
Men's Katahdin Performance Flannel Shirt-Jacket, Hi-Pile Fleece-Lined Plaid
Price was from: $130 now: $49.99

A durable, eucalyptus plaid shirt-jacket with hi-pile fleece lining and insulated sleeves for extra warmth.

Pros: High quality Durable Great warmth Stylish appearance Soft fabric
Men's Tropicwear Shirt, Plaid Long-Sleeve
Price was from: $79.95 now: $67.99

A dark amber plaid long-sleeve shirt with UPF 50+ protection, built-in stretch, and excellent venting.

Pros: High quality Effective sunblock Well-made Cool and comfortable fabric Good fit
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged cream twill flannel shirt with Donegal flecks, slim fit, and button-down collar.
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $64.95 now: $54.99

A pink plaid short-sleeve shirt with moisture-wicking stretch fabric and a slightly fitted untucked fit.
Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
Price was from: $59.95 now: $50.99

A vintage indigo plaid chambray shirt with built-in stretch, perfect for untucked wear and easy movement.

Men's Check Shirts

Men’s check shirts have long been a cornerstone of versatile wardrobes, offering a blend of tradition, comfort, and easygoing style that fits seamlessly into a variety of settings. Whether you’re reaching for a black check shirt for men to layer over a favorite tee for weekend errands or choosing a bold check shirt to add some personality to your everyday rotation, these shirts strike a unique balance between casual comfort and classic appeal. The distinctive grid pattern—formed by intersecting lines in contrasting or complementary colors—has roots in outdoor heritage and workwear, but today’s check shirts are just as likely to be spotted at a backyard barbecue as they are on a hike through the woods. Many men appreciate the way a big box check shirt for men can make a statement without feeling overdone, while others gravitate toward more subtle, traditional patterns that pair well with everything from jeans to khakis. The range of fabrics, from lightweight cotton to cozy flannel, ensures that a check shirt is just as comfortable on a breezy summer evening as it is layered under a jacket when cooler weather rolls in.

These shirts are a favorite for their adaptability—ideal for anyone with a busy, active lifestyle who wants to move easily from work to weekend without missing a beat. Casual check shirts are especially popular for family gatherings, outdoor adventures, or simply relaxing at home, thanks to their relaxed fit and easy-care fabrics. For those looking to refresh their closet without breaking the bank, there are plenty of options that deliver quality and style at a reasonable price point, making it easy to find cheap checked shirts that don’t compromise on durability or comfort. Gifting a check shirt is also a thoughtful gesture, whether it’s for Father’s Day, a birthday, or just to surprise someone who appreciates timeless style—these shirts are a welcome addition to any man’s wardrobe, and their universal appeal means they suit a wide range of ages and tastes. The check pattern itself has a way of evoking memories of time spent outdoors, shared meals around a campfire, or simple moments with friends and family, making each shirt feel personal and connected to the restorative power of being outside.

When choosing a check shirt, it’s worth considering the occasion and how you plan to wear it. Lighter, breathable fabrics are perfect for warmer days or layering over a tee, while heavier flannels add warmth and texture as the seasons shift. The variety of fits—from relaxed to tailored—ensures there’s a style for everyone, whether you’re looking for something roomy for extra comfort or a more polished silhouette for dinners out or casual Fridays at the office. For those seeking a shirt that can transition from casual to more refined settings, exploring options like Mens Occasion Shirts can offer additional inspiration. Ultimately, men’s check shirts are about more than just pattern—they’re about making everyday moments a little easier, a little more comfortable, and a lot more memorable, no matter where your day takes you.

It's time to upgrade your browser

Men's Check Shirts