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Men’s Relaxed Fit Button-Ups

Find men’s relaxed fit button-ups with a roomier cut for those who prefer a less fitted shirt. Explore button-up shirts in an easygoing silhouette, and check individual size and fit details to help choose the right one for you.

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Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
A vintage indigo plaid chambray shirt with moisture-wicking cotton blend and built-in stretch for comfort.
(0)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
A breathable brown cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.
(1,159)
$74.95 $54.99
SALE
$74.95 $54.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
A breathable brown plaid chambray shirt in a cotton blend with stretch and a relaxed untucked fit.
(845)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe
A breathable red cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.
(294)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Cloud Gauze Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Cloud Gauze Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
A superlight gray long-sleeve shirt made from breathable, crinkled 100% cotton gauze for warm weather.
(0)
$69.95 $34.99
SALE
$69.95 $34.99
SALE
Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
A super-soft orange plaid oxford shirt in 100% cotton with a relaxed, untucked fit and button-down collar.
(0)
$69.95 $59.99
SALE
$69.95 $59.99
SALE
Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
L.L.Bean Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
A super-soft gray striped cotton oxford shirt with a relaxed fit and button-down collar, perfect untucked.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Comfort Stretch Performance® Button-Front Knit Shirt, Long-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Button-Front Knit Shirt, Long-Sleeve
A lightweight blue button-front shirt in a moisture-wicking Pima cotton and polyester blend piqué fabric.
(0)
$89.95 $89.95
SALE
$89.95 $89.95
SALE
Men's Sunwashed Twill Shirt, Slightly Fitted Untucked Fit
L.L.Bean Men's Sunwashed Twill Shirt, Slightly Fitted Untucked Fit
A lightweight orange cotton twill shirt with a button-down collar, front pocket, and subtle slub texture.
(0)
$69.95 $59.99
SALE
$69.95 $59.99
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
A lightweight gray cotton twill shirt featuring a soft brushed finish and a relaxed untucked fit.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
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 in a soft TENCEL™ lyocell-polyester blend with a textured, relaxed look.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
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
SALE

Men’s Relaxed Fit Button-Ups

Men’s relaxed fit button-ups bring a roomier silhouette to a familiar shirt style, pairing a full-button front with a cut that sits farther from the body than a close-fitting shirt. The appeal is straightforward: a classic look without a narrowly shaped outline. Relaxed fit generally describes additional room through the body, although the exact measurements and proportions depend on the shirt. It is a fit description, not simply another name for a larger size. Choosing a relaxed cut in the appropriate size can create a different shape than sizing up in a more fitted design, which also changes the collar, sleeves, and overall length. Those distinctions matter when a shirt looks right across the chest but feels out of proportion elsewhere. Shoulder placement, sleeve length, and the way the hem falls all contribute to the finished look. A shirt can have a generous body while still looking thoughtfully proportioned, with a collar that frames the face and cuffs that land where expected. For men who prefer a less closely tailored silhouette, this balance is often the reason to choose relaxed fit in the first place. The button-up design adds its own familiar character, from the line of buttons down the front to the shape of the collar. Button-up and button-down are sometimes used interchangeably, but they describe different details: a button-up closes with buttons down the front, while a button-down has collar points that fasten to the shirt. That difference can help clarify descriptions when comparing styles. Neither term alone establishes the fit, so the relaxed fit designation remains an important part of the picture. Taken together, the cut, collar, and front closure give this category its identity: recognizable men’s shirts with a more generous shape and plenty of room for individual style.

The visual character of a relaxed fit button-up comes from the relationship between its proportions and its details. A plain front lets the shirt’s shape take the lead, while a pattern adds another point of interest. Smaller patterns tend to read differently from broad, more prominent designs, and the spacing of a pattern can matter as much as its colors. A chest pocket, a defined button placket, or a contrasting button can change the overall impression without changing the basic shirt silhouette. Collar size also plays a part: a more compact collar creates a different balance from a broader one, particularly when the top button is left open. These are useful distinctions for anyone who likes the familiarity of a button-up but has a clear preference about how much detail a shirt should have. Hem shape and shirt length deserve similar attention. A curved hem and a straighter hem create different outlines, and the same shirt length will fall differently on people of different heights and proportions. A photograph can show the overall design, while measurements offer a more concrete basis for comparison. Setting those measurements alongside a shirt that already has the desired fit can make the differences easier to picture. The goal is not to find the loosest possible shirt, but to find the right relationship between roominess and proportion. Personal style matters just as much: some men prefer a simple, understated shirt, while others gravitate toward a more noticeable pattern or a distinctive collar. Neither approach needs a closely fitted cut to look considered. For a related category with a more specific material and collar description, explore Relaxed Fit Cotton Button-Down Shirts. Keeping fit, fabric information, and collar construction distinct makes it easier to understand what each description actually tells about a shirt, rather than treating similar-sounding names as identical.

A thoughtfully chosen shirt starts with accurate details rather than assumptions about the category. Relaxed fit describes the cut; it does not establish fabric composition, fabric weight, care requirements, or specialized features. Those details belong to the individual shirt’s description and care label. Material information is worth reviewing alongside close-up photographs, since color and pattern alone cannot explain how a fabric is constructed or how it should be maintained. Likewise, a relaxed silhouette does not indicate whether a shirt requires ironing or a particular washing or drying method. Following the stated care instructions, including any directions for buttoning, washing, drying, and pressing, keeps the routine tied to the actual garment. Durability is another consideration best grounded in construction details and appropriate care, rather than inferred from the fit name or appearance. Clear views of seams, button attachments, cuffs, and the collar can offer useful context when assessing the workmanship. For intended use, the individual description is the place to confirm any stated recommendations; a roomy cut alone does not establish a shirt’s suitability for a particular activity. This attention to detail is equally helpful when choosing a shirt for someone else. A relaxed fit button-up can be a thoughtful gift for a man who already favors generous shirt proportions and a classic button-front look. His usual shirt size is a starting point, but the fit of a favorite shirt can reveal more: whether he likes extra room at the waist, where he prefers the hem to fall, and which collar shapes he reaches for most often. Familiar patterns and understated details may be more meaningful than choosing something dramatically different from his established taste. For a personal purchase, the same observations help bring the choice into focus. A collar that looks right, sleeves of the appropriate length, and the desired amount of room through the body are concrete details that distinguish one shirt from another. Men’s relaxed fit button-ups offer a clear starting point for that choice, combining a familiar shirt design with a roomier silhouette that leaves personal preference at the center.
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