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In every man's life comes the time when he realizes a supreme truth of life, which is that, at a certain point, he 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, or even a button-up. 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; a button-front just has buttons...on the front. 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-ups.
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 high-waisted 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.
J.Crew 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.
For those prone to breaking out into a slight sweat on their way to the office or date night, this is the moisture-wicking, breathable shirt for you.
Everlane 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.
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Madewell Sunday Flannel Perfect Long-Sleeve Shirt
Madewell's heavyweight button-down is comfy AF, so you feel like you're wearing a blanket, but look a little more business-y.
Uniqlo Oxford Striped Slim-Fit Long-Sleeve Shirt
Uniqlo Oxford Striped Slim-Fit Long-Sleeve Shirt
Whether unbuttoned atop a white tank or buttoned to the top with a skinny tie, there's no going wrong with a slim, striped button-down.
The cool thing about this shirt—aside from its fit and chic color options, all made from natural dyes derived from minerals—is that it's 100 percent biodegradable and compostable. You're basically wearing the earth.
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Few—and we mean very few—can surpass Lululemon's ability to offer sleek, uber comfortable styles meant to move with you.
Polo Ralph Lauren The Iconic Oxford Shirt
Polo Ralph Lauren The Iconic Oxford Shirt
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.
Wythe New York Moleskin Western Pearl Snap Shirt
If you're looking for a reason to ball out a bit over budget, the reason is pearl snap buttons.
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Levi's 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.
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.
The looks of an oxford button-down, with the durability of workwear.
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Todd Snyder co*cktail Oxford Long-Sleeved Button-Down
For a unique, laidback effect, this double-patterned button-down looks cool while retaining its classiness.
The hardwearing, work-ready option.
Brooks Brothers Stretch Regent Regular-Fit Sport Shirt
Brooks Brothers Stretch Regent Regular-Fit Sport Shirt
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
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Abercrombie & Fitch Long-Sleeve Performance Button-Up Shirt
Abercrombie & Fitch Long-Sleeve Performance Button-Up Shirt
This moisture-wicking option retains its casual chicness.
A classic, neutral flannel that's ready to pair with just about anything.
Thom Browne Button-Down Collar Striped Grosgrain-Trimmed Cotton Oxford Shirt
Thom Browne Button-Down Collar Striped Grosgrain-Trimmed Cotton Oxford Shirt
Now 40% Off
It's hard to talk about button-downs (or any classic menswear piece, really) without bringing up Thom Browne. Luckily, he makes an ultra-clean, simple shirt—so we don't have to.
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Carhartt Loose Fit Heavyweight Corduroy Jersey-Lined Long-Sleeve Shirt
Thick corduroy + a modern cut = a match made in functional fashion heaven.
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.
