The 15 Best Button-Down Shirts for Men

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For used to A button-down shirt is a tough proposition. Buttons? You talking about buttons?

fingers made soft and flabby by months of doing nothing but navigating the ins and outs of pullover

Turns out, buttoning a shirt is like riding a bike—once you know how, it's hard to forget.

washed OCBDs

brushed flannels so plush

And now that we're well into the dog days of winter (and you've really started dressin') there's five types of essential button-downs you should be thinking about.

It's time to put those soft, flabby fingers to use, baby! Let's get to buttoning.

In every man's life, there comes a time when he realizes a supreme truth: At a certain point, he shouldn't be thinking about anything more than the essential button-down shirt.

When we say "button-down shirt," what we really mean is a button-front (or button-up) shirt. Now, that's not the most technically correct definition. Properly speaking, a button-down shirt is a shirt on which you can quite literally button down the collar points, while 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 some thoroughly scuffed slip-ons à la Brad Pitt. 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 outside the box, you can't wrong.

The Relaxed Poplin Shirt

This modern option from Everlane is crisp, clean, and made with 100% lightweight poplin cotton for all-day breathability. Roll up the sleeves and pair it with a relaxed pant for the ultimate casual look.

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.

Flex Long-Sleeve Shirt

Dickies is a stalwart of American-made workwear, and this hardwearing option is essential for guys who like to get their hands dirty (or keep them clean).

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. Cowboy boots and chaps not included.

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.

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.

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. This shirt is what we call a true chef's kiss.

Easy Care Checked Stretch 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.

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.

Denim Point Collar Shirt

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, Todd Snyder's take is a no-brainer.

Porto Shirt

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.

Linen Button Down Shirt

Scotch & Soda makes its fashion functional with adjustable sleeves—so whether you're strolling along the beach or enjoying a sunny day in the city, you can embrace your individuality.

Tomlin Cotton Oxford Shirt

This easy-fitting button-down is a timeless option and looks chic with just about everything (for a casually cool look, we suggest pairing it with your best jeans and a pair of sleek black loafers).

Airflex Shirt

The name doesn't lie with this style. Engineered with ultra-lightweight fabric that wicks away sweat and refuses to wrinkle, this everyday button-down is made to move with you.

Tech Button-Down Shirt

For those prone to breaking out into a slight sweat on their way to the office or date night (a dirty martini also helps ease the nerves), this is the moisture-wicking, breathable shirt for you.

How To Choose

There are two primary things to consider before you pull the plug on a button-down of your own. Fit and fabric, the 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.

Why You Should Trust Us

We’re not going to say something is great unless it’s actually great.

Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams. When it comes to button-down shirts, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse for their own wear.

We’ve had to go through a lot of trial and error, and these button-down shirts are the ones that are simply the best. Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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