A Sneakerhead's Guide to Wearing Denim

A lot of guys pick a size for themselves, convince themselves it fits, and just roll with it until they learn otherwise. Are you really a 32 or a 36? Should you buying a 32-inch inseam or a 34-inch inseam? You can attempt to measure yourself, but you’re better of going to a tailor, a denim shop like Self Edge, or even your local J.Crew. They’ll let you know which size pants you should be wearing. This is the most important obstacle to tackle. Once you find your correct pant size, it becomes much easier to dodge #ntdenim in the future.

A tailor isn’t just the guy to go to when you have a wedding to attend or score a new job. They can assist you to make sure all of your daily garments fit your awkward body. Denim tailoring isn’t as common, but it can slim the legs of too-baggy jeans or shorten an inseam. Raw denim often comes in longer lengths, and a tailor can easily turn your 38-inch inseam jeans into a 31”. Make sure, however, that your jeans are given a chainstitch when they’re shortened. A majority of sneaker and jean combo problems happen because the jeans are too long, and this is the easiest way to remedy that problem.This will ensure no one knows your jeans had work done on them, and they’ll let your Air Maxes see the light of day (for once).

The name says it all: Bootcut jeans were designed to be worn with boots. And if you ask denim nerds, most will prefer a pair of straight-leg to cover their Red Wing or Danner boots. Not only do bootcut jeans flare out and cover sneakers, they often drag on the ground, rip, or fray. This cut of denim should only be reserved for dudes who wear square-toed shoes and tent-shaped “going out” shirts. As someone who takes pride in their appearance, specifically their sneakers, you should never strive to be associated with guys who dress like crap.

If all else fails, there are always jogger pants. The elasticized or cuffed pants pants have become popular with sneakerheads over the past few years. That’s because they completely skirt the issue of #ntdenim all together. They fit like a pair of slim sweatpants but are acceptable to wear in public and to most cool jobs. Even easier, most sneaker boutiques or stores sell a version of jogger pants - most notably, New York’s Kith and its Mercer pants. The cuff of a jogger pant sits above any sneaker and is the simplest way to show them off.

The most difficult issue when trying to avoid #ntdenim is learning which pants goes with which sneaker. A straight-leg jean might be OK with a pair of Air Jordan XIIIs or Foamposites, but it might cover a Jordan Future or Nike Flyknit Racer. Slimmer cut jeans are better worn with sneakers that hug close to the ankle or have a very thin tongue. In reverse, sneakers with thick ankle padding or fat tongues can be worn with almost any jean that doesn’t have an exaggerated cut or actually fits.

Pinrolling jeans, also known as “pegging,” started in the ‘80s. It’s done by folding in a part of the pant inseam and cuffing the pants, and it creates a tight-to-the-ankle effect on the jeans. Right now, this trend has been revived amongst European sneakerheads who prefer runners and previously wore track pants. The pin rolling of a jean will make them fit just like track pants from the ‘90s, and your sneakers will be on display for everyone to see. The look hasn't quite caught on in the States, but it's a better option than looking like it's 2003 all over again.

Jeans have been around since the mid-1800s, and cuts and details have evolved over the history of the blue jean. Some styles, such as the Levi’s 501, will never go out of style. But if you own baggy-fit, lightwash carpenter jeans from 2003—and they’re still you’re daily go-to jeans—throw them out ASAP. The same goes for jeans that look like they were worn by Jerry Seinfeld or Tim Allen. It’s time to embrace the new, and your old jeans are keeping you stuck in #ntdenim land. And keep your sneaker game from getting the recognition it deserves.

Even if a jean fits correctly, it can still look awful if it’s too long. This can easily be remedied by a single or double cuff of the jeans. Not only does a cuff shorten a pant’s length, it can also show off sought-after hem on a pair of selvedge denim. When in doubt that jeans are covering too much of a sneaker, just give them a cuff. And if you want to avoid the issue all together, just cuff them above the ankle.

There’s a fear amongst men on the subject of “slim jeans.” They immediately associate the word “slim” with skinny and future generation-crushing thoughts come to mind. We’re hear to inform you: Not all slim-cut jeans will show the goods or cut off circulation. Guys of all shapes and sizes can wear jeans that aren’t baggy and won’t mess up their sneaker presentation. There are plenty of straight-leg, slim-straight, or slim-cut jeans that gave enough room to feel comfortable in, but they won’t restrict blood flow or rip if you bend over. Go to the store, try on a few different cuts and find out which one works for you. Your sneakers will thank you in the long run.

There’s a common misconception that buying premium or even raw selvedge denim means that someone won’t get stuck with #ntdenim. This isn’t true at all. There are plenty of expensive jeans that are unflattering—hello, True Religion—and raw denim brands that produce looser fits: For example, the A.P.C. “New Rescue.” Take a look at Michael Jordan, all of his jeans are bespoke. And by contrast, a pair of Levi’s 511s or 501s can be had for under $40. Just because a jean costs more money doesn’t mean it’s better. It’s all about personal preference, just like sneakers.