Classic Casual Shirts

Classic casual shirts from L.L.Bean are the perfect blend of comfort and timeless style, designed to effortlessly complement any wardrobe. Whether you're heading out for a weekend adventure or enjoying a laid-back day at home, these shirts offer the versatility you need. With an array of colors and patterns to choose from, finding the right look has never been easier. Each shirt is crafted with quality materials, ensuring durability and lasting value that you can count on. Embrace the outdoors with confidence and ease in our classic casual shirts, ready to accompany you on every journey.

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298 Items

Men's Scotch Plaid Flannel Shirt, Traditional Fit

A soft, 100% Portuguese cotton flannel shirt in authentic Scottish tartan with a relaxed traditional fit.

Pros: Fits well Good quality Softness Warmth Comfortable
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: Beautiful design Roomy fit Warmth Durable Superior softness
Men's Scotch Plaid Flannel Shirt, Slightly Fitted

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

Pros: High quality Perfect fit Softness Warmth Comfortable
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 construction Versatile for spring and fall Great color options Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Price was from: $69.95 now: $54.99

A red check button-down shirt made of 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 durability Comfortable fit
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
Price was from: $59.95 now: $44.99

A red checked short-sleeve shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Wrinkle-free and stays crisp Great fit and true to size Lightweight and breathable Attractive color and print options Comfortable and soft fabric
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free white cotton shirt with a traditional fit, offering a freshly pressed look without ironing.

Pros: High quality Perfect fit Wrinkle-free Professional look Versatile
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

A wrinkle-free, bright blue tattersall oxford shirt in 100% cotton with a traditional relaxed fit.

Pros: High quality Consistent sizing Wrinkle-free Durable Comfortable fit
Men's Tropics Shirt, Short-Sleeve Print

A breathable blue cotton shirt with a relaxed fit and weathered look for hot days.

Pros: Durable quality Versatile style Cool and lightweight Great summer look Comfortable fit
Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve

A green cotton short-sleeve shirt with a relaxed fit, featuring durable stitching and button-flap pockets.

Pros: Versatile and stylish Perfect fit Durable and sturdy Soft and lightweight Comfortable to wear
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $69.95 now: $54.99

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

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: $69.99

A slim-fit chamois flannel shirt in forest shade vintage ducks, made from 100% cotton flannel.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

An indigo long-sleeve chambray shirt with built-in stretch, perfect for wearing untucked.

Pros: High quality Versatile design Soft fabric Good stretch Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A green chambray shirt with stretch, moisture-wicking cotton blend, perfect for untucked casual wear.

Pros: High quality material Well made Good stretch Soft fabric Comfortable fit
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $54.99

A gray, wrinkle-free, brushed cotton shirt with a slightly fitted untucked fit for ultimate comfort.

Pros: Great fit High quality Attractive appearance Wrinkle-free Comfortable fabric
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid

A breathable blue plaid chambray shirt in a cotton blend with stretch and a relaxed untucked fit.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve

A green chambray shirt with built-in stretch, moisture-wicking cotton blend, and a relaxed untucked fit.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged brown cotton flannel shirt with a soft brushed finish and classic yarn-dyed plaid pattern.
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe

A breathable blue cotton-blend chambray shirt with stretch, moisture-wicking fabric, and a relaxed untucked fit.
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe

A blue striped chambray shirt in a breathable cotton blend with stretch and moisture-wicking comfort.
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A green plaid long-sleeve shirt in a breathable cotton blend with stretch and moisture-wicking comfort.
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $74.95 now: $59.99

A pale khaki chambray shirt with built-in stretch, moisture-wicking cotton blend, and untucked 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 Signature Washed Field Shirt, Slim Fit
Price was from: $89 now: $74.99

A rugged brown herringbone cotton shirt with a slim fit and vintage-inspired details.

Classic Casual Shirts

Classic casual shirts have long been a staple in wardrobes for good reason: they’re built to handle whatever the week brings, from relaxed weekends to spur-of-the-moment gatherings with friends. There’s something special about reaching for a shirt that’s as comfortable as it is reliable, with timeless style that fits in anywhere—whether you’re heading out for a backyard barbecue, a quick hike on the local trail, or just enjoying a quiet evening on the porch. As the days get longer and the weather warms up, these shirts become even more essential. Lightweight cottons, airy linens, and soft blends keep you cool and comfortable, while classic button-fronts and easy pullovers offer versatility that’s hard to beat. They’re easy to layer over your favorite tee or under a light jacket, making them a go-to choice for unpredictable spring and early summer weather. The right casual shirt should feel effortless—something you can throw on in the morning and wear straight through to dinner with the family, always looking put-together without a second thought.

When choosing a classic casual shirt, there are a few things to keep in mind that can make all the difference. Look for details like well-finished seams, sturdy buttons, and fabrics that get softer with every wash—these are the hallmarks of shirts made to last, year after year. A good fit ensures you’re comfortable whether you’re reaching for a frisbee or relaxing by the campfire, and classic patterns like checks, stripes, and solids never go out of style. These shirts also make thoughtful gifts for just about anyone on your list. They’re a great way to celebrate milestones, mark a birthday, or simply show someone you care. With so many options, it’s easy to find a style that suits your favorite uncle, your best friend, or even your hard-to-shop-for dad. And because they’re so versatile, classic casual shirts are just as at home at a Saturday morning farmers’ market as they are at a family reunion or a casual dinner out. If you like to mix things up, you might also want to explore our collection of Classic Tees—another timeless choice for everyday comfort and style.

There’s a certain satisfaction in finding a shirt that feels just right, one you’ll reach for again and again as the seasons change. Classic casual shirts are designed for real life—easy to care for, ready to go wherever you do, and always up for a little adventure. Whether you’re packing for a weekend getaway, updating your work-from-home rotation, or simply looking for a shirt that fits your everyday routine, you’ll appreciate the lasting quality and thoughtful details that set these shirts apart. They’re made to move with you, to stand up to the demands of busy days and spontaneous plans, and to offer comfort you can count on. With each wear, they become more familiar, more uniquely your own, ready to be part of new memories and everyday moments alike.