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Mens Roll Up Sleeve Shirts

Find men's roll-up sleeve shirts you can wear with the sleeves down or rolled up. Browse the selection and compare each shirt’s fit and design details to find the right match for your wardrobe.

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Men's Tropicwear CoolPro Fishing Shirt, Long-Sleeve
L.L.Bean Men's Tropicwear CoolPro Fishing Shirt, Long-Sleeve
A blue long-sleeve fishing shirt in polyester-nylon fabric with UPF 50+, cooling stretch and odor resistance.
(0)
$89.95 $49.99
SALE
$89.95 $49.99
SALE
Men's VentureStretch Woven Shirt
L.L.Bean Men's VentureStretch Woven Shirt
A multicolor, moisture-wicking stretch ripstop shirt with nylon, TENCEL™ Lyocell, spandex and mesh-lined chest pockets.
(0)
$79 $54.99
SALE
$79 $54.99
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
A soft blue cotton long-sleeve tee that resists shrinking, wrinkles, fading and pilling wash after wash.
(10,664)
$36.95 $36.95
SALE
What customers like:
Durable and well-made
Variety of colors
Maintains shape and color
High-quality fabric
Comfortable fit
$36.95 $36.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
A blue cotton long-sleeve henley shirt that resists shrinking, fading, wrinkles and pilling.
(6,468)
$44.95 $44.95
SALE
What customers like:
Perfect fit
No shrinkage
Durable fabric
True to size
Soft and comfy
$44.95 $44.95
SALE
Men's Two-Layer River Driver's Shirt®, Traditional Fit, Henley
L.L.Bean Men's Two-Layer River Driver's Shirt®, Traditional Fit, Henley
A blue wool-blend henley with two-layer thermal construction, soft cotton lining, and quick-drying warmth.
(6,147)
$79.95 $79.95
SALE
What customers like:
Versatile and stylish
Beautiful color options
High quality and durability
Warmth and coziness
Comfortable fit
$79.95 $79.95
SALE

Mens Roll Up Sleeve Shirts

Mens Roll Up Sleeve Shirts bring a relaxed detail to a familiar wardrobe favorite. There’s something about a neatly rolled sleeve that makes a shirt feel a little more personal—the same classic look, worn your way. As you browse, consider how you like the sleeves to sit: a narrow, even fold creates a tidier finish, while a wider roll gives the shirt a more casual appearance. Look closely at the product photos and descriptions to understand the sleeve design, cuff shape and any details intended to hold a roll in place. Those small differences are worth comparing, especially if you have a favorite sleeve length. Start with a style you genuinely like, then look at the details that distinguish one shirt from another rather than assuming every roll-up design works the same way.

A good place to begin with fit is a shirt you already enjoy wearing. Compare its measurements with the individual size chart, paying attention to the shoulders, chest, sleeves and overall length rather than relying on the size label alone. Think about the silhouette you prefer, too: a closer fit gives a different look from a roomier cut, and the right choice is the one that feels like you. Product photos can help you judge proportions, but measurements offer a more useful point of comparison. If you prefer an untucked look, take a moment to check the hem shape and shirt length. For the sleeves, consider both how they look fully extended and where you want the rolled cuff to land. A shirt should appeal to you as a whole, not just because of one detail.

Color and pattern are another opportunity to make the choice your own. Take a look at the pants and other shirts you reach for most often; they offer a practical starting point for finding something that belongs in your wardrobe. A familiar color can make a new shirt easy to pair, while a different pattern can add variety without taking you far from your usual style. Roll-up sleeve shirts can also be a thoughtful gift for someone who appreciates classic clothing with a relaxed touch. Picture the person’s favorite shirt—the color they choose again and again, the way they wear the hem, the sleeves folded just below the elbow—and let those preferences guide you. Checking their usual measurements and the shirt’s care instructions adds a little extra thought to the choice. The most personal gift is often something that reflects how someone already likes to dress.

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