Help Me Dress Myself: How to Buy Pants That Fit Correctly

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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. But don’t fret: With some advice from McKenzie Dowler, lead stylist at Rag & Bone, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at buying the perfect pants.

Step 1: Know Your Cuts

You should have three different pant cuts on your radar: straight leg, slim and super skinny. As a general rule, it works like this: For a trendier, hipper (dare we say, hipster) look, super skinny is your best bet. If you don’t feel like you can pull off that look, but still want a fashionable, fitted silhouette, choose slim cut. And if you’re just looking for a day-to-day relaxed pair of pants, go with a straight leg—which, as far as today’s fashion police are concerned, is the new relaxed fit. Sorry, baggy fans.

Step 2: Go With Whatever Suits Your Body Type

At the end of the day, you should just choose what’s right for you. According to Dowler, it’s all about (a) what you’re comfortable in (you’re not going to look cool if you’re waddling self-consciously down the street, worrying about how your new super skinny jeans are strangling your privates); and (b) what exhibits your best features. “If you have great calves, wear skinny pants to show them off,” Dowler recommends. “If you have tiny calves but a great butt, wear a straight leg that emphasizes your behind.”

Step 3: When All Else Fails, Cheat

There’s one more option for those looking for both comfort and trendiness: the tapered leg. “Tapered pants sort of resemble the shape of a carrot—they’re not really tight in the crotch area and on the thighs, but they gradually get slimmer toward the ankle,” Dowler explains. “They’re a great option for older guys who are in search of comfort when putting together a wardrobe.”

Step 4: Get The Length Right

First things first, your pants should absolutely never touch the floor, even at the back. If they do, visit a tailor to get them hemmed ASAP. Now that that’s out of the way, let’s talk about the perfect pant length: “You want to see what I call a ‘break’ at the ankle—meaning there should be a tiny fold or divot right where your ankle bone [that small knob of bone protruding from the side of your ankle] is,” Dowler explains. “That way, the pants aren’t so long they’re covering your entire shoe, but you also have enough material to roll them up if you’re wearing a boot or a high-topped sneaker.” Or, in simpler terms, the bottoms of your pants should sit just about half an inch below the tops of your shoes.

Step 5: Avoid The Sag

“I always tell guys that they should be able to fit two fingers maximum in their waistband,” Dowler explains. “That way, they won’t fall off if you’re not wearing a belt, and you won’t see a bunch of ruching [small creases on your waistband] if you do decide to wear a belt.” Plus, two fingers worth of room gives you just enough space to enjoy a hearty lunch without popping a button.

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