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Men's Relaxed Fit Shorts

Shop men's relaxed fit shorts for a roomier alternative to slim-fitting styles. Browse the selection and compare each pair’s sizing, inseam and fit details to find the shape and length you prefer.

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Men's Tropic-Weight Cargo Shorts, Comfort Waist, 10"
L.L.Bean Men's Tropic-Weight Cargo Shorts, Comfort Waist, 10"
A pair of lightweight, breathable 100% cotton cargo shorts with elastic side panels for ultimate comfort.
(3,006)
$54.95 $54.95
SALE
What customers like:
High quality
Perfect fit
Lightweight material
Deep pockets
Comfortable
$54.95 $54.95
SALE
Men's Tropic-Weight Cargo Shorts, Comfort Waist, 6"
L.L.Bean Men's Tropic-Weight Cargo Shorts, Comfort Waist, 6"
A pair of tan, 100% cotton shorts with a comfort waist and practical cargo pockets.
(2,011)
$54.95 $54.95
SALE
What customers like:
Lightweight fabric
Practical pockets
High quality
Versatile style
Comfortable fit
$54.95 $54.95
SALE
Men's L.L.Bean Allagash Cargo Shorts, 10"
L.L.Bean Men's L.L.Bean Allagash Cargo Shorts, 10"
A pair of ultrarugged 100% cotton cargo shorts with multiple pockets and a 10" inseam.
(1,777)
$64.95 $44.99
SALE
What customers like:
Durable material
Great color options
High quality construction
Comfortable fit
Roomy pockets
$64.95 $44.99
SALE
Men's Dock Shorts, 8"
L.L.Bean Men's Dock Shorts, 8"
A pair of 8" organic cotton twill shorts with an adjustable drawstring waist in coastal dune.
(1,664)
$49.95 $49.95
SALE
What customers like:
Lightweight and durable
High quality
Versatile design
Great color options
Comfortable fit
$49.95 $49.95
SALE
Men's Wrinkle-Free Double L® Chino Shorts, Natural Fit, Hidden Comfort Waist, 8"
L.L.Bean Men's Wrinkle-Free Double L® Chino Shorts, Natural Fit, Hidden Comfort Waist, 8"
A pair of wrinkle-free khaki shorts with hidden elastic waist, made from premium 100% cotton.
(1,377)
$54.95 $54.95
SALE
What customers like:
Wrinkle-proof fabric
High quality
Perfect fit
Comfortable waistband
Durable
$54.95 $54.95
SALE
Men's Sport Shorts with SUPPLEX® fabric, 8"
L.L.Bean Men's Sport Shorts with SUPPLEX® fabric, 8"
A versatile pair of blue nylon shorts with UPF 50+ protection and quick-drying, anti-odor liner.
(1,374)
$44.95 $37.99
SALE
What customers like:
High quality
Attractive design
Fast-drying material
Versatile use
Comfortable fit
$44.95 $37.99
SALE
Men's Sport Shorts with SUPPLEX® fabric, 6"
L.L.Bean Men's Sport Shorts with SUPPLEX® fabric, 6"
A versatile pair of blue nylon sport shorts with quick-drying, UPF 50+ SUPPLEX® fabric and mesh liner.
(1,262)
$44.95 $37.99
SALE
$44.95 $37.99
SALE
Men's L.L.Bean Multisport Shorts, 9"
L.L.Bean Men's L.L.Bean Multisport Shorts, 9"
A versatile pair of blue shorts with UPF 50+, offering stretch and quick-dry comfort for active days.
(1,176)
$64.95 $64.95
SALE
What customers like:
Quick-dry fabric
Great looks
Lightweight comfort
Versatile design
True to size
$64.95 $64.95
SALE
Men's Tropicwear Shorts, 9"
L.L.Bean Men's Tropicwear Shorts, 9"
A redesigned pair of gray shorts with SunSmart™ fabric, offering comfort, stretch, and sun protection.
(372)
$74.95 $74.95
SALE
What customers like:
Stylish look
Secure pockets
Lightweight material
Good ventilation
Comfortable fit
$74.95 $74.95
SALE
Men's L.L.Bean Multisport Shorts, 7"
L.L.Bean Men's L.L.Bean Multisport Shorts, 7"
A versatile pair of blue shorts with stretch, quick-dry fabric, and UPF 50+ sun protection.
(274)
$64.95 $44.99
SALE
What customers like:
Perfect fit
Wrinkle resistance
Comfortable material
Deep pockets
Lightweight design
$64.95 $44.99
SALE
Men's Wide-Wale Cord Pull-On Shorts, 7"
L.L.Bean Men's Wide-Wale Cord Pull-On Shorts, 7"
A pair of gray cotton-blend corduroy shorts featuring wide-wale texture, elastic waist, and built-in stretch.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
SALE
Men's Access Trail Shorts, 9"
L.L.Bean Men's Access Trail Shorts, 9"
A versatile pair of green shorts with UPF 50+ protection, made from a quick-drying nylon blend.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Everyday Poplin Shorts, Standard Fit, 8"
L.L.Bean Men's Everyday Poplin Shorts, Standard Fit, 8"
A lightweight gray cotton-blend short with built-in stretch and an 8" inseam for easy movement.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's VentureStretch Chino Shorts, 7"
L.L.Bean Men's VentureStretch Chino Shorts, 7"
A versatile pair of gray shorts with a nylon-spandex blend, offering UPF 50+ protection and durability.
(0)
$69.95 $44.99
SALE
$69.95 $44.99
SALE
Men's Comfort Stretch® Chino Shorts, 8"
L.L.Bean Men's Comfort Stretch® Chino Shorts, 8"
A breathable blue cotton/CoolMax blend short with built-in stretch and an 8" inseam for comfort.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Mountainside Ripstop Shorts, 8"
L.L.Bean Men's Mountainside Ripstop Shorts, 8"
A lightweight, gray short made from a durable cotton-nylon blend with UPF 50+ sun protection.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Field Chino Shorts, 7"
L.L.Bean Men's Field Chino Shorts, 7"
A rugged pair of gray cotton-blend chino shorts with stretch twill and garment-washed softness.
(0)
$69.95 $54.99
SALE
$69.95 $54.99
SALE
Men's BeanFlex® Performance Canvas Shorts, 9"
L.L.Bean Men's BeanFlex® Performance Canvas Shorts, 9"
A rugged brown canvas short made from a soft, stretchy TENCEL cotton blend for everyday comfort.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
SALE
Men's Comfort Stretch Performance® Everywhere Chino Shorts, 6"
L.L.Bean Men's Comfort Stretch Performance® Everywhere Chino Shorts, 6"
A lightweight gray chino short made from a soft, stretchy cotton-nylon blend for all-day comfort.
(0)
$74.95 $74.95
SALE
$74.95 $74.95
SALE
Men's Comfort Stretch Performance® Everywhere Chino Shorts, 8"
L.L.Bean Men's Comfort Stretch Performance® Everywhere Chino Shorts, 8"
A versatile pair of blue chino shorts made from a soft, stretchy cotton-nylon blend twill fabric.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
SALE
Men's Sunwashed Khaki Shorts, 7"
L.L.Bean Men's Sunwashed Khaki Shorts, 7"
A pair of blue peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Sunwashed Khaki Shorts, 9"
L.L.Bean Men's Sunwashed Khaki Shorts, 9"
A pair of gray peached twill shorts offering lived-in softness, stretch comfort, and classic everyday style.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE

Men's Relaxed Fit Shorts

Men’s relaxed fit shorts offer a familiar, easygoing look with roomier proportions than a closely cut style. For men who prefer a little more space through the seat and thigh, that shape can be an important part of finding a pair that feels like their own. Relaxed fit describes the cut, not a reason to choose a larger waist size: the starting point is still a waistband that fits properly, with the extra room coming from the way the shorts are shaped. The overall effect depends on more than the fit label, too. Length, the line of the leg opening, and the relationship between the waistband and the hem all influence how a pair looks. A shorter inseam leaves more of the leg visible, while a longer one brings the hem closer to the knee; the same measurement can fall differently on men of different heights and proportions. Someone who already has a favorite pair can use its measurements as a useful point of comparison, especially when deciding between two lengths. Picture the difference between a hem that sits clearly above the knee and one that meets it: both can have a relaxed shape, but each creates a distinct silhouette. That makes personal preference more useful than a rigid rule about where shorts should end. A familiar waist measurement, a preferred rise, and a sense of how much room feels right through the thigh help narrow the choices without changing the character of the style. The appeal is straightforward: a classic shorts shape that leaves room for individual taste, whether that means a neater outline or a fuller profile. Rather than following a passing look, relaxed fit shorts can reflect the proportions a man has long preferred and the simple details he reaches for again and again.

The character of men’s relaxed fit shorts also comes from the way their proportions work with the rest of a wardrobe. A straight-hanging shirt creates a different outline from one tucked neatly into the waistband, and the amount of fabric above the waist changes the visual balance of a roomier leg. An untucked hem that ends well above the bottom of the shorts leaves their shape visible; a longer shirt can obscure that shape and make the shorts appear shorter than they are. These small relationships often matter more than putting together an entirely new look. Familiar tees, collared shirts, and simple layers provide reference points for deciding which length and profile best suit a personal style. Color adds another consideration, with quieter shades creating a different impression from a more noticeable contrast between top and bottom. Neither approach needs elaborate coordination. A wardrobe built around a few favorite colors can make the choice feel natural, especially for someone who likes getting dressed without reconsidering every detail. The individual product descriptions are the place to compare fabric composition, construction, and finishing details, rather than assuming every pair with the same fit name has the same qualities. Relaxed fit alone does not identify a material, a fabric weight, or a particular capability. Similarly, the details at the waist, the placement of pockets, and any visible stitching are worth considering as part of each pair’s overall appearance. For a separate selection centered on cotton, explore Mens Comfortable Cotton Shorts. Keeping those distinctions clear makes it easier to choose by the qualities that actually matter to the wearer. The result need not be a carefully coordinated outfit; often, the most appealing combination is simply a familiar shirt, a preferred shorts length, and proportions that look right together. Timeless style leaves plenty of room for that kind of individual choice.

A thoughtful choice of relaxed fit shorts takes the details beyond appearance into account without expecting the fit label to tell the whole story. Sizing information, care directions, and the description of each pair provide separate pieces of the picture. Where measurements are supplied, they are more helpful than guessing from a photograph alone. A waistband can look similar across two styles while the rise or leg shape differs, and a familiar size does not necessarily mean every cut will fit identically. Taking a moment to compare those details is especially worthwhile for someone replacing a much-loved pair whose proportions have become second nature. Care deserves the same attention. The label on the individual garment should determine washing and drying, rather than a general assumption about how shorts ought to be treated. For someone who prefers a straightforward clothing routine, reviewing those directions before choosing can be just as important as selecting a color or length. Durability is another consideration best explored through the stated construction details of a particular pair, not inferred from a roomy silhouette or a substantial-looking photograph. Any requirements for a specific activity should likewise be checked against the individual description; relaxed fit identifies a shape, not a promise about performance. These distinctions are useful when choosing a gift, too. Men’s shorts can be a personal, practical choice for a partner, father, brother, or friend when the giver knows the recipient’s usual size and preferences. A favorite pair offers clues: where the waistband sits, how far the hem falls above the knee, and whether the leg opening is broad or more restrained. Matching those familiar preferences often matters more than choosing something noticeably different. For men selecting their own shorts, the same approach keeps the focus on what they genuinely like wearing. Across changing seasons and shifts in personal style, roomier proportions, a preferred length, and well-considered details remain useful reasons to choose relaxed fit.
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