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Men's Relaxed Fit Polo Shirts

Find men's relaxed fit polo shirts with a roomier cut for those who prefer a less fitted shape. Explore classic polo styling, and compare each shirt’s fit details and size chart to help choose the right size for you.

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Men's Mountainside Micro Waffle Polo, Long-Sleeve
L.L.Bean Men's Mountainside Micro Waffle Polo, Long-Sleeve
A durable, quick-drying red polo made from a soft recycled polyester blend with moisture-wicking waffle fabric.
(0)
$79.95 $67.99
SALE
$79.95 $67.99
SALE
Men's Casco Bay Rugged Polo, Short-Sleeve, Print
L.L.Bean Men's Casco Bay Rugged Polo, Short-Sleeve, Print
A rugged blue cotton polo with contrast trim and a relaxed fit for untucked style.
(0)
$54.95 $34.99
SALE
$54.95 $34.99
SALE
Men's Premium Double L® Polo, Banded Short-Sleeve Without Pocket
L.L.Bean Men's Premium Double L® Polo, Banded Short-Sleeve Without Pocket
A gray, all-cotton pique-knit polo with wrinkle-, fade-, shrink- and pill-resistant performance and a relaxed fit.
(8,093)
$44.95 $44.95
SALE
$44.95 $44.95
SALE
Men's Premium Double L® Polo, Hemmed Short-Sleeve with Pocket
L.L.Bean Men's Premium Double L® Polo, Hemmed Short-Sleeve with Pocket
A wrinkle-resistant green cotton polo with a no-roll collar, pocket, and relaxed traditional fit.
(2,956)
$44.95 $44.95
SALE
What customers like:
Great fit
High quality
Attractive color
Comfortable style
Durable material
$44.95 $44.95
SALE
Men's Carefree Unshrinkable Polo, Short-Sleeve, Without Pocket
L.L.Bean Men's Carefree Unshrinkable Polo, Short-Sleeve, Without Pocket
A blue short-sleeve polo made from soft, wrinkle-resistant cotton that resists shrinking and fading.
(0)
$39.95 $39.95
SALE
$39.95 $39.95
SALE
Men's Casco Bay Rugged Polo, Short-Sleeve, Stripe
L.L.Bean Men's Casco Bay Rugged Polo, Short-Sleeve, Stripe
A rugged striped cotton piqué polo with contrast trim and a relaxed fit for untucked style.
(0)
$54.95 $44.99
SALE
$54.95 $44.99
SALE
Men's Casco Bay Rugged Polo, Short-Sleeve
L.L.Bean Men's Casco Bay Rugged Polo, Short-Sleeve
A rugged green polo in breathable cotton piqué with contrast trim and a relaxed untucked fit.
(0)
$49.95 $39.99
SALE
$49.95 $39.99
SALE
Men's Premium Double L® Polo, Long-Sleeve Without Pocket
L.L.Bean Men's Premium Double L® Polo, Long-Sleeve Without Pocket
A long-sleeve, unshrinkable white polo made from supersoft cotton pique-knit, designed for a relaxed fit.
(5,065)
$54.95 $54.95
SALE
What customers like:
High quality
Well-made
True to size
Versatile
Comfortable fit
$54.95 $54.95
SALE
Men's Casco Bay Rugged Polo, Long-Sleeve, Stripe
L.L.Bean Men's Casco Bay Rugged Polo, Long-Sleeve, Stripe
A long-sleeve striped polo in breathable 100% cotton piqué with contrast trim and a relaxed fit.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Carefree Unshrinkable Polo, Long-Sleeve, Without Pocket
L.L.Bean Men's Carefree Unshrinkable Polo, Long-Sleeve, Without Pocket
A brown long-sleeve polo made from soft, wrinkle-resistant cotton that resists shrinking and fading.
(0)
$44.95 $44.95
SALE
$44.95 $44.95
SALE
Men's Casco Bay Rugged Polo, Long-Sleeve
L.L.Bean Men's Casco Bay Rugged Polo, Long-Sleeve
A long-sleeve yellow cotton piqué polo with contrast trim and a relaxed, untucked fit.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
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Men's Comfort Stretch Performance® Pima Polo, Short-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Pima Polo, Short-Sleeve
A purple short-sleeve polo with quick-dry Pima cotton blend and UPF30 sun protection.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Everyday SunSmart® Polo 2.0, Short-Sleeve Stripe
L.L.Bean Men's Everyday SunSmart® Polo 2.0, Short-Sleeve Stripe
A breathable, multi-color striped polo with UPF 50+ protection and stretch for active comfort.
(0)
$59.95 $29.99
SALE
$59.95 $29.99
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Men's Everyday SunSmart® Polo 2.0, Short-Sleeve
L.L.Bean Men's Everyday SunSmart® Polo 2.0, Short-Sleeve
A breathable blue polo with UPF 50+ protection, offering stretch and moisture-wicking for active comfort.
(0)
$54.95 $34.99
SALE
$54.95 $34.99
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Men's Ultralight Adventure Polo, Long-Sleeve
L.L.Bean Men's Ultralight Adventure Polo, Long-Sleeve
An ultralight brown long-sleeve polo made from quick-drying, moisture-wicking, pill-resistant polyester.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Comfort Stretch Performance® Polo, Short-Sleeve, Slightly Fitted, Stripe
L.L.Bean Men's Comfort Stretch Performance® Polo, Short-Sleeve, Slightly Fitted, Stripe
A lightweight blue polo in a Pima cotton blend, perfect for work or travel.
(0)
$64.95 $40.99
SALE
$64.95 $40.99
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Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve, Print
L.L.Bean Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve, Print
A relaxed, ultrasoft short-sleeve shirt in a multicolor TENCEL™ lyocell and polyester blend with a fun print.
(0)
$74.95 $59.99
SALE
$74.95 $59.99
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Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve
L.L.Bean Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve
A gray short-sleeve shirt crafted from an ultrasoft TENCEL™ lyocell and polyester blend with textured finish.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
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Men's Comfort Stretch Performance® Party Polo, Slightly Fitted, Short-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch Performance® Party Polo, Slightly Fitted, Short-Sleeve, Stripe
A green striped polo in a breathable cotton blend with moisture-wicking, quick-dry, and UPF 50+ protection.
(0)
$59.95 $49.99
SALE
$59.95 $49.99
SALE
Men's Comfort Stretch Performance® Party Polo, Slightly Fitted, Short-Sleeve, Print
L.L.Bean Men's Comfort Stretch Performance® Party Polo, Slightly Fitted, Short-Sleeve, Print
A lightweight, moisture-wicking polo in fun multicolor prints with UPF 50+ sun protection and stretch.
(0)
$59.95 $49.99
SALE
$59.95 $49.99
SALE
Men's Comfort Stretch Performance® Polo, Short-Sleeve, Slightly Fitted
L.L.Bean Men's Comfort Stretch Performance® Polo, Short-Sleeve, Slightly Fitted
A moisture-wicking blue polo in a Pima cotton blend, perfect for versatile everyday wear.
(0)
$54.95 $26.99
SALE
$54.95 $26.99
SALE
Men's Comfort Stretch Performance® Polo, Long-Sleeve, Slightly Fitted
L.L.Bean Men's Comfort Stretch Performance® Polo, Long-Sleeve, Slightly Fitted
A lightweight blue long-sleeve polo in a moisture-wicking Pima cotton/polyester blend for versatile wear.
(0)
$59.95 $44.99
SALE
$59.95 $44.99
SALE
Men's All Seasons Cotton Blend Sweater, Short-Sleeve Polo
L.L.Bean Men's All Seasons Cotton Blend Sweater, Short-Sleeve Polo
A superlight tan polo sweater in a soft cotton-nylon blend for everyday comfort and versatility.
(0)
$49.95 $49.95
SALE
$49.95 $49.95
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Men's Bean's Vintage Soft Rugby, Stripe
L.L.Bean Men's Bean's Vintage Soft Rugby, Stripe
A multi-color jersey-knit cotton rugby shirt with a twill collar and authentic rubberized buttons.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
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Men's Relaxed Fit Polo Shirts

Men’s relaxed fit polo shirts bring a little more room to a familiar, timeless style. A polo’s collar and buttoned neckline give it a distinct look, while a relaxed fit offers an alternative to a closely shaped silhouette. The appeal is in that balance: a shirt that looks considered without looking tightly fitted. In general, relaxed fit describes extra room through the body compared with a more fitted cut, though the exact proportions depend on the design and size. It does not automatically mean oversized, boxy, or dropped at the shoulders. Those descriptions refer to different aspects of a shirt’s shape, and the distinction matters when choosing a polo with a particular look in mind. A boxy silhouette emphasizes width relative to length; an oversized silhouette deliberately adds volume; a relaxed silhouette generally takes a less close-fitting approach without necessarily changing every proportion. For someone who prefers a little space through the chest and waist, that makes the fit description more useful than a photograph alone. Shoulder placement, sleeve shape, and overall length all contribute to the result. Two polos in the same labeled size can look noticeably different if one has a straighter body or a longer hem. The most helpful comparison is often a polo already in the closet: one with the preferred shoulder position, the right amount of room through the middle, and a length that feels in proportion. That familiar reference makes it easier to interpret size information without assuming that every relaxed fit follows the same pattern. The goal is not simply a bigger shirt, but a shape that suits the person wearing it. This collection centers on that easygoing approach to a classic, with men’s relaxed fit polo shirts offering a straightforward starting point for those who prefer their clothing less closely cut.

Proportion gives a relaxed polo its character, and small differences can matter more than a size label suggests. A shoulder seam that sits near the shoulder creates a different outline from one that extends beyond it, just as a sleeve ending higher on the arm changes the balance of the shirt. Neither detail alone defines relaxed fit. Instead, the shoulders, chest, body, sleeves, and hem work together to establish the silhouette. Choosing a larger size in a more fitted polo is not necessarily equivalent to choosing a relaxed cut in the usual size: the larger size may also change the neckline, shoulder width, sleeve length, and overall length. For that reason, the stated fit and measurements deserve attention alongside the size. A shirt laid flat offers a useful visual reference, especially when comparing body width and length with a favorite already owned. There is no single hem position that works for every man; height, torso length, and personal preference all influence where a polo looks balanced. An untucked hem leaves the shirt’s full outline visible, while a tucked hem changes how the fullness appears at the waist. Styling preferences can help narrow the choice without turning relaxed fit into a rigid set of rules. Straight-cut pants can echo the polo’s easy proportions, while a more defined trouser shape creates a contrast with the fuller top. Color and pattern add another layer of personal choice, whether the preference is for a quiet combination or a shirt that stands apart from the rest of an outfit. The collar and neckline provide a familiar point of definition in either case. A relaxed polo does not need to resemble an oversized shirt to have an easygoing appearance, and it does not need to follow a passing trend to feel personal. The strongest choice is one whose proportions feel familiar enough to wear with confidence while reflecting the wearer’s own sense of style.

Beyond shape, choosing a polo involves details that are best considered shirt by shirt. Material composition, construction, and care directions belong to each individual design; the words “relaxed fit” describe the cut rather than establishing a particular fabric or maintenance routine. Reading those details keeps expectations grounded and helps distinguish shirts that may look similar in a photograph. For a related selection, Men's Relaxed Cotton Polos provides another way to browse while keeping a preferred silhouette in mind. Within any selection, the product description and care label are the right references for understanding what a shirt is made of and how it should be washed and dried. A familiar laundry routine can be a useful consideration, but it should not replace the directions supplied with the garment. Long-term satisfaction also involves more than the initial appearance: the accuracy of the fit, the quality of the finishing, and whether the shirt’s care requirements suit the owner all deserve a place in the decision. Close-up images can help clarify visible details such as the collar shape, the button opening, and the hem, without requiring assumptions about how every polo is constructed. Those same considerations are helpful when a polo is intended as a gift. A man who already favors relaxed silhouettes offers a clearer starting point than a size alone, whether the recipient is a partner, father, brother, or friend. Knowing how he likes his shirts to sit at the shoulders and through the waist can be more valuable than guessing which look he might adopt. A favorite polo’s size and proportions, along with familiar color preferences, provide practical clues while leaving room for a thoughtful choice. Ultimately, men’s relaxed fit polo shirts appeal through a recognizable combination of classic styling and a less fitted shape. Attention to the details keeps the selection personal, with the emphasis on a polo that belongs naturally alongside the clothing its owner already enjoys.
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