Relaxed Fit Button-Down Shirts

Relaxed fit button-down shirts are a timeless choice for easygoing comfort and effortless style, whether you’re heading out for a weekend adventure or enjoying downtime with friends and family. Designed to offer plenty of room to move, these shirts make it simple to layer or wear on their own. With classic details and versatile colors, relaxed fit button-down shirts are ready to keep up with your every day, season after season.

Sort by:

Filter & Sort

476 Items

Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Price was from: $69.95 now: $58.99

A wrinkle-free cotton shirt in a relaxed fit with moisture-wicking TrueCool® fabric and a check pattern.

Pros: Perfect fit Wrinkle-free Durable Comfortable Beautiful colors
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit

A crisp, wrinkle-free white cotton shirt with a relaxed fit and pearlized buttons for easy care.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A breathable brown chambray shirt in a cotton blend with stretch 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 a relaxed untucked fit.
Men's Maine Guide Sherpa Lined Wool Shirt

A ultra-warm wool blend shirt with recycled sherpa fleece lining, featuring a relaxed fit and multiple pockets.
Men's Lakewashed Performance Shirts, Button-Front Shirt, Short-Sleeve, Print
Price was from: $64.95 now: $47.99

A blue cotton-blend short-sleeve shirt with moisture wicking, stretch, UPF 50+ protection, and fun prints.
Women's Vacationland Seersucker Shirt, Short-Sleeve Popover Plaid
Price was from: $49.95 now: $36.99

A relaxed-fit plaid popover shirt crafted from ultra-soft, cool cotton seersucker with a curved hem.
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit Plaid

A blue plaid cotton shirt with a relaxed fit, wrinkle-free finish, and pearlized buttons.
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check

A blue check button-down shirt made of wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
Price was from: $59.95 now: $44.99

A gray plaid short-sleeve chambray shirt in a breathable, moisture-wicking cotton blend with added stretch.
Women's Signature Soft Poplin Shirt
Price was from: $99 now: $48.99

A versatile white cotton poplin shirt with a relaxed fit and oversized front pockets.
Women's Whisperweight Flannel Shirt, Button-Down
Price was from: $69.95 now: $51.99

A superlight dark black flannel shirt with a relaxed fit and curved high-low hem for year-round comfort.
Women's Camden Hills Button Front Shirt, Print
Price was from: $69.95 now: $49.99

A relaxed-fit white shirt in a soft TENCEL™ blend with a unique print and button-front placket.
Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
Price was from: $69.95 now: $59.99

A super-soft brown striped oxford shirt in 100% cotton with a relaxed, untucked fit.
Women's Essential Cotton Shirt, Chambray Long Sleeve

A lightweight blue cotton chambray shirt with a relaxed fit, button-front placket, and single chest pocket.
Women's Essential Cotton Poplin Shirt, Long-Sleeve
Price was from: $64.95 now: $54.99

A versatile multi-color stretch poplin shirt with a relaxed fit, crafted from 95% cotton and 5% spandex.
Men's Sunwashed Twill Shirt, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $59.99

A lightweight blue cotton twill shirt with a button-down collar, subtle texture, and untucked fit.
Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $59.99

A super-soft blue plaid oxford shirt in 100% cotton with a relaxed, untucked fit and button-down collar.
Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
Price was from: $59.95 now: $44.99

A vintage indigo plaid chambray shirt with moisture-wicking cotton blend and built-in stretch for comfort.
Men's Signature Seersucker Madras Shirt, Slightly Fitted, Short-Sleeve
Price was from: $69.95 now: $34.99

A breezy red short-sleeve shirt made from 100% cotton seersucker with a slightly fitted design.
Women's Signature Linen-Blend Button-Front Shirt, Three-Quarter-Length Sleeve
Price was from: $99.95 now: $74.99

A relaxed, oversized shirt in a cool linen-rayon blend with three-quarter cuffed sleeves and a draped fit.
Men's Comfort Stretch Performance® Button-Front Knit Shirt, Long-Sleeve

A lightweight green button-front shirt in a moisture-wicking Pima cotton and polyester blend piqué fabric.
Women's Sunwashed Twill Shirt
Price was from: $69.95 now: $58.99

A relaxed-fit green cotton twill shirt, garment washed for vintage appeal and all-season comfort.
Camden Hills Tee, Button-Front Shirt
Price was from: $64.95 now: $44.99

A relaxed-fit purple tee in a soft TENCEL™ blend with button-front placket and shirred shoulders.

Relaxed Fit Button-down Shirts

Relaxed fit button-down shirts have become a go-to choice for anyone seeking comfort, ease, and timeless style in their everyday wardrobe. With their roomier cut, these shirts offer a laid-back silhouette that allows for unrestricted movement—whether you’re reaching for a mug on the top shelf, wrangling kids in the backyard, or simply enjoying a slow morning on the porch. The relaxed fit is especially appreciated as the days grow longer and warmer, or as the air takes on a crisp edge during the transition to cooler months. You’ll often find these shirts crafted from soft, breathable fabrics like cotton, linen, or lightweight blends, all chosen for their comfort and versatility. Many feature dropped shoulders, a wider chest, and straight hems, making them just as easy to wear untucked over a favorite tee as they are buttoned up for a casual dinner out. The beauty of a relaxed fit button-down is in its adaptability—it’s equally at home layered over a tank top during a weekend at the lake, or paired with chinos for a relaxed office look.

These shirts make thoughtful gifts for just about anyone in your life, from the college student heading off to campus, to the busy parent who values both comfort and style, to the retiree who appreciates a classic piece that never goes out of fashion. They’re a staple for travel, too—easy to pack, easy to wear, and just as suitable for a stroll through the farmers’ market as for lounging by the campfire. For those who like to express their personality through subtle details, relaxed fit button-downs come in a wide range of colors, patterns, and textures, from crisp whites and gentle pastels to bold checks and nature-inspired prints. Subtle details like chest pockets, contrast stitching, or softly faded washes add extra character. When selecting a relaxed fit button-down, consider the fabric weight and sleeve length that best suits your lifestyle—short sleeves for the heat of summer, or long sleeves that can be rolled up as the day warms. With their easygoing nature and classic good looks, these shirts become fast favorites, ready for everything from backyard barbecues to impromptu road trips. If you’re looking for more inspiration or want to explore a full range of options, you can find a curated selection of Men’s Relaxed Fit Button-Ups designed to fit right into your everyday adventures.

FAQs

Relaxed fit button-down shirts are incredibly versatile and can be styled in many ways. Wear them untucked over jeans for a casual look, layer them over a tee or tank for added warmth, or tie them at the waist for a laid-back, outdoorsy vibe. They also pair nicely with chinos or shorts when the weather warms up, and can be dressed up with a belt and loafers for a polished yet comfortable outfit.

Yes, relaxed fit button-down shirts are a great option for layering during colder months. Their roomier cut allows for easy layering over base layers or under sweaters and jackets, helping you stay warm and comfortable as temperatures fluctuate.

Absolutely. Relaxed fit button-down shirts offer a timeless style that works well for both casual get-togethers and more semi-formal events. Choose a classic solid color or subtle pattern for a dressier look, or opt for bold plaids and prints for a more relaxed, everyday feel.

Relaxed fit button-down shirts are often made from durable, comfortable fabrics like cotton, flannel, chambray, or linen blends. These materials are chosen for their softness, breathability, and ability to hold up well through frequent wear and washing.

Yes, relaxed fit button-down shirts make thoughtful gifts for friends and family. Their classic style and comfortable fit make them a go-to choice for a wide range of ages and personal styles, and they're suitable for many occasions throughout the year.

It's time to upgrade your browser

Relaxed Fit Button-Down Shirts