The 25 Best Button-Down Shirts Are Worth Building Your Wardrobe Around

Now that we’re well and truly going out and about—feel ready to really start dressin’—you shouldn’t be thinking about anything more than the essential button-down shirt.

There are two primary things to consider before you pull the plug on a button-down of your own. Fit and fabric, enduring pillars of any smart clothing purchase, are of paramount importance. Luckily, though, there have never been more, or better, options. Technical fabrics that resist wrinkles or wick moisture sound nice but are usually better suited to workout gear than your button-down rotation. And fabric technology has come a long way since the starchy, grating dress shirts of years past, which means even the most traditional of styles—in hardy oxford cloth, soft flannel, silky viscose and rayon, or lightweight cotton poplin—now feel as comfortable as any of the best fleece-lined pieces in your closet. As for fit, it’s perfectly okay to opt for a more relaxed style if the shirt in question is cut intentionally boxy, but otherwise it’s best to stick to a slimmer silhouette; they tend to be more flattering on a wide range of body types.

Before we move on, a brief note: When we say “button-down shirts,” we really mean any button-front shirt. That’s not the most technically correct way of doing things; a button-down shirt, properly, is a shirt on which you can quite literally button down the collar points. But language evolves, and most folks aren’t being that specific when they use the term. So you’ll find a lot of shirts here, some of which are proper Button-Downs and some of which are, y’know, equally good button-downs.

Chief among them? The oxford-cloth button-down, the flannel button-down, the denim button-down, the printed button-down, and finally, the trusty overshirt. Some combination of this motley crew will always make for an all-star lineup in your regular rotation. Try pairing a beefy flannel with slouchy denim and a some thoroughly scuffed slip-ons a la Brad Pritt. Or, hell, a striped OCBD with summer-ready trousers, retro sneakers, and maybe even a hat up top. As long as you’re trying, and thinking a little outside of the box, you really can’t go wrong.

Flex Long-Sleeve Shirt

Dickies

Now 27% off

The hardwearing, work-ready option.

Organic Flannel Shirt

The flannel shirt’s wide-ranging appeal speaks to the timeless nature of its design. There really is one for everyone, from your grungy younger brother, who prefers his long and slouchy, to your deeply disappointed dad, who prefers his sturdy and substantial enough to stand up to the residual debris it’ll encounter as an accessory to any grisly household chores. Case in point: The Bean’s soft, organic cotton option.

Barstow Western Denim Shirt

Levi’s, an OG of the denim scene if there ever was one, makes a Western-inspired style as good as they come.

Mixed Bandana Patchwork Short Sleeve Cotton Sport Shirt

Native Youth

Why settle for one nifty pattern when Native Youth offers a patchwork button-down with many?

The Slim Fit Japanese Oxford Shirt

Slim and shrunken, or big and baggy are two go-to button-down silhouettes. Everlane’s decidedly modern option splits the difference.

Bowery Wrinkle-Free Stretch Cotton Shirt

Ah, gingham: a classic, foolproof pattern that’ll work in any setting. And J.Crew undoubtedly does it best.

Baviera 2 Pocket Check Shirt

Portuguese Flannel

A Portuguese Flannel button-down made out of super-soft, premium flannel. (And crafted—you guessed it!—in Portugal.)

The High Sierra Flannel

California Cowboy

Soft, sturdy, and supremely comfortable. (It’s even lined with an insulating thermal layer, so you’ll definitely be warm when winter hits.)

Whiting Shirt

Wax London

As close to Brad Pitt and his—probably vintage, definitely perfect— topper as any of us are ever going to come.

Stretch Regent Regular-Fit Sport Shirt

Brooks Brothers

If you’re a guy who counts the number of pleats at a sleeve’s cuff, you’re a guy who fully understands the power and everlasting quality of Brooks Brothers. Since the 1800s, the brand, reputedly the oldest in the apparel industry, has been offering gentlemanly styles

The Iconic Oxford Shirt

Polo Ralph Lauren

Though it was Brooks Brothers that brought the essential ingredients to the masses, it was Ralph Lauren who refined the recipe, damn near perfecting it over the decades.

Venture Long Sleeve Shirt

Few—and we mean very few—can surpass Lululemon’s ability to offer sleek, uber comfortable styles meant to move with you.

Needles 7 Cuts Tie Dye Flannel Shirt

Each season, Needles makes a bunch of its distinctive, fan-favorite flannels, and each season they manage to look like someone let Dr. Frankstein loose in the fabric warehouse in the best way possible.

Viscose Shirt

This breezy viscose button-down from Stüssy is absolutely primed for high rollers.

Blanket Shirt

Outerknown

Outerknown signature heavyweight shirt is so soft and so insulating that it’s worth copping three of more of the myriad colors and patterns that are available.

Bone Button Western Shirt

Flint and Tinder

Simple, streamlined, and always in style.

Italian Midweight Denim Shirt

Todd Snyder

Todd Snyder’s mid-weight denim shirt is proof that when you want to give an American icon an elegant upgrade, you simply turn to the fabric maestros in Italy.

Shoals Denim Shirt

Billy Reid

There’s no disputing the denim shirt is an icon. We could tout its stylistic merits six ways to Sunday, but suffice to say if there’s one piece of classic Americana actually worthy of the superlative, it just might be the—often blue, always sexy—denim button-down. For those looking to hop on the bandwagon, Billy Reid’s take is a no-brainer.

Beach Cotton Shirt

Rag & Bone

You can always count on Rag & Bone to bring a streetwise edge to its collections—even styles, like this checkered button-down, that made of beach-ready materials.

Travis Camp-Collar Printed Woven Shirt

Orlebar Brown

Orlebar Brown’s bright button-down is fresh, fruity, and perfect for summer.

Alaskan Check Shirt

Woolrich’s padded overshirt—in a classic buffalo check near-synonymous with the brand—might not be the last one you’ll ever want, but it’s sure as hell the last one you’ll ever need.

Slim-Fit Button-Down Collar Cotton Oxford Shirt

Thom Browne

OCBDs have been a staple of Thom Browne’s collections, and a briskly selling one at that, since the sly American designer starting putting his signature twist on them in the mid aughts.

+ Tim Lehi Camp-Collar Printed Woven Shirt

Wacko Maria

Designer Atsuhiko Mori never fails with the fiercest prints. Just take a look at the button-down: you can practically hear the roar.

Rowdy Oversize Plaid Snap-Up Camp Shirt

Bianca Saunders

Bianca Saunders is a rising star in menswear, a designer that plays with proportions and patterns to stunning effect. Here’s proof.

Print Cotton Button-Up Shirt

Off-White x Pablo Tomek

Off-White’s Virgil Abloh and Pablo Tomek: two visionaries whose works raised street culture to the level of high art.

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Source : Esquire