Sneakerheads can be really obsessive.

Sneakerheads can be obsessive about cleaning their sneakers, about silhouettes and colorways and collaborations, about release dates, about posting their kicks to Instagram. From the outside looking in, sneakerheads probably do seem a bit tuned into the particulars — it's all about the tiny details, the waxed laces, the soft leathers, the extra dust bags, and the special edition boxes.

Given this preoccupation with minutiae, it's funny that some sneakerheads have no idea what pants to wear. Of course, there isn't one "right" way to wear a certain pair of shoes with a certain pair of pants, but clearly many trainer enthusiasts become so fixated with what's on their feet that they really aren't considering anything they're wearing above the ankles.

Sneakerheads (as well as regular people who wear shoes) are constantly working to solve this riddle, and we've seen this co-dependent relationship between shoes and pants evolve over the years. In the mid-'80s when the Lugz craze took hold, it wasn't uncommon to cinch your pants (Lee jeans were the most popular) with a rubber band, or even with tape, to avoid treading on the hem.

After being popularized by b-boys, drug dealers also adopted the style to indicate they were "holding," as well as urban cyclists as to not become tangled in their bike chain.

Not long after, LL Cool J started walking around in public with one pant leg rolled up, and his home of Queens, New York City, followed suit, although each borough made a point of proudly having its own style. It was assumed that LL was aiming to bring more attention to his footwear with this move, but he later clarified (kind of) to The Guardian: "You know what? I have huge left calf muscles. They need room to breathe. I haven't done that for years though. It's just a style from New York."

Today, we even break the issue down with terms like "jean lay," and we incessantly crave "fit pics" on Reddit and Facebook groups. We've come up with solutions like the jogger pant, largely popularized by Publish Brand who actually trademarked this term to describe the popular fit. We know the jogger pant works with virtually any pair of sneakers, but was perhaps just a prolonged excuse to publicly wear pajamas that look acceptable with everything from Air Force 1s to Rick Owens.

Around 2014, mostly every streetwear and fashion brand under the rainbow from Balmain to H&M was making their own version of Publish's tapered sweatpants with a ribbed ankle, but since then we've seen many brands retire that specific silhouette from shelves.

Many of us have also dabbled in pin-rolling, a practice that European sneakerheads in particular can't seem to get enough of, even when wearing jeans that are already really skinny. Americans have tried it too, but much like grime and rolling your weed with tobacco, we've only seen limited success Stateside.

Pin-rolling calls back as early as the early '40s zoot-suit era when pants were "pegged" or rolled and tightened at the cuff. But today many sneakerheads pin-roll as an easy fix when their jeans are too loose at the ankle.

Of course, there's always the "tucking-your-pants-into-your-socks" move, a look that is enjoyed by the likes of Shia LaBeouf, Kanye West, and high school wrestling teams. And when summer rolls around, sneakerheads become even more confused about how to wear sneakers with shorts.

In our social media-driven world of #outfitgrids and #snobshots, having the rarest pair of sneakers isn't all it takes to flex anymore, and sneakerheads have indeed started breaking out their wallets for more than just a new pair of sneakers, especially the younger generation.

But what truly separates sneakerheads from fashion obsessives is that we always get dressed from the ground up, and today a wider variety of sneakers—from timeless models like the adidas Gazelle to futuristic interpretations like the ACRONYM x NikeLab Air Force 1 Downtown—means there is more variety in what to wear in general.

It goes without saying, Common Projects call for a different choice of pants than something from Y-3, and figuring out this balance takes a bit of trial and error, so don't be afraid to fail. Even Michael Jordan—the namesake of the most popular line of signature athletic footwear in history—could use some help in picking out a new pair of jeans. But we suppose even he missed a few jumpers in his day.

A great place to start is to look at clothing brands that use sneakers to add an extra accent to their clothes. The reason why labels like John Elliott, Public School, UNDERCOVER, and ACRONYM get sneaker collaborations in the first place is because the designers are sneakerheads themselves.

If you're a bit more budget-conscious, over time these designers go onto influence larger trends, eventually resulting in more affordably priced versions of their gear from fast-fashion shops and lower-priced labels. With that in mind, maybe consider foregoing that next sneaker drop in favor of a couple of new trousers instead.

The views and opinions expressed in this piece are those solely of the author, and do not necessarily reflect the position of Highsnobiety as a whole.

  • Main & Featured Image:@glasscitymike

What To Read Next

  • Image on Highsnobiety

    Kim Is a Roma Fan, Who Knew?

  • Image on Highsnobiety

    Chris Black & Jason Stewart Keep It Cozy With MATCHESFASHION

  • Image on Highsnobiety

    New Balance Brings the "Protection Pack" to the 1906D

  • Image on Highsnobiety

    A Moment Please For Brad Pitt's Big Orange Puffer

  • loewe resale

    You Can Bag Loewe for Under Retail at StockX Right Now

  • Image on Highsnobiety

    Tom Sachs' Nikecraft GPS Sneaker Returns in 2023

*If you submitted your e-mail address and placed an order, we may use your e-mail address to inform you regularly about similar products without prior explicit consent. You can object to the use of your e-mail address for this purpose at any time without incurring any costs other than the transmission costs according to the basic tariffs. Each newsletter contains an unsubscribe link. Alternatively, you can object to receiving the newsletter at any time by sending an e-mail to

Web Accessibility Statement

Titelmedia (Highsnobiety), is committed to facilitating and improving the accessibility and usability of its Website, Titelmedia strives to ensure that its Website services and content are accessible to persons with disabilities including users of screen reader technology. To accomplish this, Titelmedia has engaged UsableNet Inc, a leading web accessibility consultant to help test, remediate and maintain our Website in-line with the Web Content Accessibility Guidelines (WCAG), which also bring the Website into conformance with the Americans with Disabilities Act of 1990.


Please be aware that our efforts to maintain accessibility and usability are ongoing. While we strive to make the Website as accessible as possible some issues can be encountered by different assistive technology as the range of assistive technology is wide and varied.

Contact Us

If, at any time, you have specific questions or concerns about the accessibility of any particular webpage on this Website, please contact us at, +49 (0)30 235 908 500. If you do encounter an accessibility issue, please be sure to specify the web page and nature of the issue in your email and/or phone call, and we will make all reasonable efforts to make that page or the information contained therein accessible for you.