A sneaker rotation is only as good as the ’fits it's being rocked with. No matter how rare the footwear you're rocking is, pair it up with the wrong pant style and you're going to end up doing a sneaker grail a huge disservice.

The rules aren't concrete, but for those putting on their pants two legs at a time, we've seen it right to offer some loose guidance to live by. Scrolling through our recent street style round-ups from Paris to New York, we've noticed a few key trends setting the pace for fashion-forward sneaker/pant combos. Using this as our inspiration, below we've outlined some of the best sneaker styles to pair with everything from smart, tailored trousers to gorpcore technical pants.

So, if you're in need of some top-line rules to ensure your 'fits are treading in the right direction, scroll on and click through for the best pants to wear with sneakers.

Bigger's Always Better

Big and chunky sneakers have almost become the norm, from Balencaga's infamous retro running models to more low-key designs from the likes of HOKA. And there's only one full-proof way of ensuring you don't end up looking like you have clown feet: wide-leg pants.

Whether you go to the extremes of Justin Bieber or keep things more low-key with a classic workwear style, doubling down on the big proportions with equally big pants is a safe bet.

Tailored Trousers with Sneakers

While pretty much any sneaker will pair well with sweatpants or jeans, combining them with tailored trousers is slightly more unfamiliar territory for our sports-inspired footwear. This might have made it a bit of a faux pas in years gone by, but that's certainly no longer the case.

Take your sneakers for a walk on the formal side with a pair of loose-fitting dress pants such as the ones below.

The Daily Sneakers With Jeans

The everyday, casual uniform for most of us: sneakers with jeans are a tried-and-tested winner. Jeans are super versatile when it comes to sneakers, more experimental baggy or flared silhouettes make for standout pairings but our favorite looks come from some of the simplest combinations.

Pairing classic sneaker silhouettes, such as the ones shown here from Converse and Reebok, with some straight-leg jeans makes for an easy-to-style and reliable option to keep coming back to.

Cozier Than Can Be

The big pro of wearing sneakers instead of other footwear styles is that they're comfier than the rest (sorry to break it to you, post-sneaker society advocates).

Naturally, that means that sneakers are the customary footwear of choice when looking at what to pair with your coziest sweatpants or, if you're that way inclined, pajama pants. Plus, with the sneaker mules we picked out, you don't even have to go through the discomfort of lacing up your kicks.

The All-Black Minimalist

If there's one style cheat code that trumps all the rest, it's that there's no going wrong when wearing all-black. That goes for those wanting to experiment with bold silhouettes and for those pulling out more sleek and minimal looks, like the pairings below.

There's no real way you can go wrong with a pair of black pants and sneakers, but two of our favorite variations are below.

Fully Weather-Proof

Whether you're about to embark on a treacherous mountain trail or a trip to the local shops, it's always better to be safe than sorry. That means putting on a pair of trail-ready sneakers along with an equally technical pair of pants.

Doubling down on GORE-TEX and waterproof fabrics, we're putting our most utilitarian foot forward with these pants and sneaker combos.

90s Classics

Baggy pants, bejeweled tops, Von Dutch trucker caps... we can't help but look back at the 90s and early 2000s without wanting our old wardrobe back. And fortunately, the continued Y2K obsession in fashion means that a lot of the styles from those years are being brought back.

Down below, we've picked out two classic sneakers and paired them with some wide-leg pants to create a look reminiscent of those younger years.

Want to keep browsing? Download the Highsnobiety app for all the hottest products and brands from the Highsnobiety Shop. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.


We Recommend
  • Workwear pants
    15 Workwear Pants That Are Clocking Overtime
    • Style
  • most comfortable sneakers
    The Most Comfortable Sneakers & Where to Buy Them
    • Style
  • Gum Sole Sneaker
    These Are the Best Gum Sole Sneakers to Shop Right Now
    • Style
  • hiking shoes
    These Hiking Sneakers Combine Style and Substance
    • Style
  • affordable sneakers
    12 Affordable Sneakers For Every Style
    • Sneakers
  • Image on Highsnobiety
What To Read Next
  • Travis Scott wears his collaborative Cactus Jack x Audemars Piguet watch
    Cactus Jack x Audemars Piguet Proves Travis Scott's Midas Touch
    • Style
  • Kanye West & wife Bianca Censori seen holding hands. Ye is wearing a black leather top, leggings & MMA shoes, Bianca is wearing a black sportsbra, grey leggings, and kitten heels
    Bound 2: Kanye & Wife Bianca Kissed & Made Up
    • Culture
  • Fossil
    Fossil Presents: Monique Billings Is Made For This
    • Style
    • sponsored
  • Fear of God Jerry Lorenzo wears a black coat and gold jewelry in front of a red backdrop
    Jerry Lorenzo on Fear of God's Long-Awaited adidas Line
    • Style
  • District Vision x New Balance FW23.
    EXCLUSIVE: District Vision Made New Balance’s Tastiest Trail Shoes Yet
    • Sneakers
  • Vans Tokyo Design Collective's first drop, including GORE-TEX Sk8-Hi sneakers and technical clothes
    Japanese Designers Are Making Vans' Clothes Cool
    • Style
*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 info@highsnobiety.com

Web Accessibility Statement

Titelmedia (Highsnobiety), is committed to facilitating and improving the accessibility and usability of its Website, www.highsnobiety.com. 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 accessibility@highsnobiety.com, +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.