8 Cool Button-Downs That Look Amazing Untucked

Logic dictates that wearing an untucked shirt should be simple. Just put on the nearest button-down and...untuck it. Here's the thing, though: Not all button-downs are created equal. Untuck the wrong shirt—one that's too long, or too baggy, or has uneven shirttails—and you'll look like a kid swimming in his dad's wardrobe. Untuck the right one, however—like, say, any of the following—and you'll look fitter, taller, and more put together than ever.

Man wearing a lilac-colored button-up shirt photo

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J.Crew Slim Stretch Secret Wash Shirt

Thanks to a catalogue of countless colors—no to mention a flattering, slim fit that's consistent across the whole spectrum—this J. Crew shirt is the type of shirt you can and indeed should buy in bulk. ($60; jcrew.com)

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Man wearing a black button up with white pattern on it photo

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The Kooples Classic Fit Print Sport Shirt

To add a touch of unique flair to your look, consider something with an irregular pattern, like this light and airy cotton shirt from The Kooples. Since it's in black-and-white, it's sure to both spice things up and slide seamlessly into your wardrobe. ($198; nordstrom.com)

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Man wearing a navy blue button-up with white pants photo

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Michael Kors Slim-Fit Embroidered Cotton Shirt

When you're looking to go untucked, the goal is to find a hem that lands in the sweet spot: not too low; not too high. For an example of where it should land, look at this shirt from Michael Kors. ($198; michaelkors.com)

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Man wearing a green plaid shirt with khaki pants photo

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Tommy Hilfiger Heathered Check Shirt

Green, gray, and white is a risky color palette. But if you're willing to try something new, the snug, flattering fit of this Tommy Hilfiger shirt will breathe vivid life into your wardrobe. ($100; usa.tommy.com)

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Man wearing a denim shirt with light khaki pants photo

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John Varvatos Star U.S.A Cotton Chambray Western Shirt

Let your inner Wild West (yes, we all have it) loose with a chambray shirt so rugged it's not hard to imagine it stopping a wayward bullet in a saloon barfight gone awry. (Not that you'd ever be in that situation, of course.) ($188; barneys.com)

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Man wearing a dark chambray shirt with jeans photo

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Kenneth Cole New York Long Sleeved Chambray Button Down Shirt

Some grays are limited in their potential: they only work with other grayscale tones. But something like this gray chambray, which has subtle hints of blue, can work with your entire wardrobe. Be brave: pair it with some brown. What's the worst that can happen? ($70; kennethcole.com)

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Red button-up shirt photo

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Polo Ralph Lauren Slim-Fit Button-Down Collar Brushed-Cotton Shirt

Studies suggest that women consider red—in all shades, but namely vivacious ones like this—the most attractive color a guy can wear. When it's displayed in a form-flattering fit like this, well, you just hit the style jackpot. ($100; mrporter.com)

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Man wearing a red plaid shirt with brown pants photo

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Barbour Dunoon Plaid Tailored Fit Button-Down Shirt

Forget everything you've ever known about plaid. This shirt, from Barbour, takes every '90s-era Seattleite's favorite pattern and blows it up for a modern, avant-garde look. ($119; bloomingdales.com)

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