Help Me Dress Myself: Getting Your Button-Down Shirt to Look Good

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Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from Jessica Chance, men’s stylist at Rag & Bone and menswear blogger, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at how to make button-down shirts look good.

Step #1: Know Your Styles

“White button-downs are dressy, checkered or printed button-downs are casual and flannels are more rock ‘n’ roll, so to speak,” Chance explains. So depending on what look you’re going for, choose accordingly. More importantly, though, Chance suggests putting the fit above all else: “Your entire outfit—no matter what—will benefit from a fitted button-down, rather than one that is oversized or too wide,” she explains. “Especially if you’re planning on wearing it untucked.”

Step #2: Know When to Tuck

“Casual light-colored or plaid button-downs typically look better untucked if you’re wearing a straight leg blue or black jean or a dark-colored chino—it’s a pretty casual combination of clothes to tuck in,” Chance says. “Again, though, the shirt needs to be fitted [slim along the sides of your torso].” If you have a shirt you really like that’s too large or too wide, however, she says tucking it in might actually benefit the outfit as a whole by slimming down your figure. In that case, Chance suggests definitely wearing a belt for a cleaner look.

Step #3: Know How Many Buttons to Unbutton

“Two should be the max—once you hit three, you start to tread into I’m-going-to-the-club territory,” Chance says. “And if you’re going for a more professional look without wearing a tie, feel free to button all the way up—that’s a classy look now.”

If you want an even more in-depth look at where, when, and why to go one or two buttons down, check out our guide to shirt buttons.

Step #4: Know Your Rolls

“If you’re going to roll your sleeves up above the elbow, makes sure the rolls are folded and clean—rather than lumpy. But if you’re rolling your sleeves midway through the forearm, make it a messy role,” Chance says. “Generally speaking, it’s safer (and more casual) to just stay below the elbow.” To avoid being too messy, Chance also recommends getting yourself a handheld garment steamer—rather than an iron—if you wear button-downs often: “They’re around $20, they’re easy to use and they’re practical. There’s no reason to own an iron or an ironing board if you have one of those.”

Step #5: If You’re Going From Formal to Casual, Take It Off

We’ve all made casual dinner plans after a less-than-casual day at work. But instead of popping open all the buttons and letting your undershirt show, Chance suggests taking the button-down off all together: “Even if you’re just wearing a white T-shirt underneath your button-down, take off the button-down and put on a jacket—or your blazer if you have to wear a suit to work. That’s an entirely different, more casual look that doesn’t feel sloppy.”

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—email us at bm@dollarshaveclub.com. We’ll have Jessica answer it in an upcoming post.