What pants to wear with sneakers

Sneakers are everywhere these days. Whether you wear athletic sneakers or you’re more into the luxury sneaker game, almost everyone has jumped on the sneaker train these days. If you haven’t, please stop reading this article and go directly to your local FootLooker. But the truth is, anyone can buy a sneaker, the art is how do you make sure your pulling them off. The first step is making sure you feel comfortable in them. Without that, you don’t have a hope in making them look cool. Next, we have to make absolutely positively sure, you don’t ruin your new sneakers with the wrong choice in pants. I have seen the coolest sneakers EVER, ruined by the person wearing the wrong leg wear… so let’s talk about some rules.

Let me help you, help yourself, and come up with some cool pant options to compliment your shoe game. Whether your dropping 1K or more on luxury kicks or wearing $50 Vans, the choice you make on pants can make or break the look.

The first big no no… wide leg dress pants. Yes, people are wearing untapered dress pants with athletic sneakers right now, I’m very aware. However, just because people are doing it doesn’t make it ok. Just look at ‘onesies’, men decided it was ok to wear onesies all of the sudden. I sure as hell didn’t go online looking for one because others wore it. In fact, I took to twitter and choose to enjoy other peoples memes on this ridiculous fad. So, please, if you rocking a sneaker with a dress pants, please get your pants tapered the right way first.

Second, stay away from anything baggy, long or loose around your kicks. It just looks sloppy.

Now, let’s focus on some cool (Kyle W. approved) ways to rock your sneakers and some rules to go by.

  1. Cropped Tapered (skinny) – Lots of companies are doing this style right now. You can get it in a track-pant style or a denim style. Here are some good companies.


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Rick Owens


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2. Cropped Tapered with a Sock – Building on the first option, you can also throw a cool sock on instead of baring your skin between the pant and shoe. I personally love Off-White socks (get the thin ones), they do a great job at making socks fun and getting more attention on your footwear.

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3. Pin-Roll – Formally know as pegging, this became popular in the 50’s with James Dean. Even in the 60’s when rolling your t-shirt sleeve was a trend, most people didn’t pin-roll  unless they were on the beach.  Fast forward to today, it’s now a great way to show off your newest pair of shoes or socks and a good way to shorten your denim/clean up the area around your shoes. Just keep in mind – pin-rolling doesn’t work with pants that are too baggy, too long, or just plain ugly (dad jeans). If you want more info on pin-rolling – let me know in the comment section.

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4. Zipper Bottoms – The zip bottoms are super trendy right now. It’s certainly a different way to rock denim. I love the way they can make a shoe look. They work with both hightop and low tops, depending on your shoe of choice. If you haven’t tried this look, give it a go.

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Represent Clo



5. The Stack -You have to be very careful with this option. First, let me explain what a ‘stack’ is if you don’t already know. A stack is how a pair of pants bunches at your footwear. A good stack should bunch about 3-5 times. Anymore can look sloppy. Also – a baggy pair of pants don’t stack, at least in a good way. You need a slim cut tapered pant to get the right look. A little stretch in the denim is a plus to help get them over your foot.

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Daniel Patrick











Many of these styles require you wearing a ‘no show’ sock. I highly recommend you have several in your wardrobe, don’t stink up your kicks. MR GRAY makes the best!

Before you go out and buy another pair of sneakers, take a minute and think about the last time you bought a new pair of pants. If you can’t remember, its time. Invest in some pants and you will be pleasantly surprised about how much better your kicks will look.  Stick with the 5 rules above and don’t let your pants minimize your shoes anymore.


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