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25 Button-Down Shirts Worth Building Your Wardrobe Around

Esquire Logo By Barry Samaha of Esquire | Slide 1 of 26: 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.

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.

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