I love casual clothes. Hoodies and jeans are my jam. It’s almost become a game for me to see how casual I can go while maintaining stylishly appropriate attire for the event. Wearing the right sneakers with the right outfit occasionally helps me achieve this. There’s a bit of an art to wearing sneakers in a manner such that you still look like a stylish guy. We’re going to go through the various “categories” of sneaker and offer a few suggestions on how you can wear them well.
Classic Casual Sneakers
First you’ve got your classic casual sneaker styles – your Vans Authentic (pictured), Converse Chuck Taylor (I just copped the new Chuck Taylor All Star IIs and LOVE them). These styles are the casual bread and butter of any guy’s sneaker game. And because they’re so casual, they take zero effort to style and wear.
How to Wear Them
Classic casual sneakers want to be a part of your low effort outfits. All white Chuck Taylors love to be paired with some medium or light blue (remember: the lighter the jean, the more casual) jeans and a t-shirt. On a hot summer day, put on your Vans slip-ons when you’re wearing some basic shorts and a tank. On the other end of the spectrum, you can pair some clean Vans slip-ons with a suit and a high-quality t-shirt for a smart, casual look.
Classic Sport Sneakers
Shoes like the ever-so-classic Nike Air Max (pictured) fall into this category. You’ll also find Adidas Stan Smiths (some might argue this choice falls under “Classic Casual”, I see no reason to argue with them on this), certain styles of New Balance, Nike Cortez, and Reebok Classics.
How to Wear Them
Ironically, even though these are sportier than the Classic Casual, I think these shoes love to be paired with your favorite pair of slim jeans or chinos (shorts are easy with sneakers, you can wear pretty much any stylish pair of shorts you want). Up top, you have almost free reign, but I think you’re best served going with a classic button up, an oxford cloth button down, or a simple sweatshirt.
What to Avoid
While sneakers are a thing these days, there are certainly many options that you should still avoid. Steer clear of running shoes. Leave those for actually running or the gym, not when you’re trying to look stylish.
While I won’t completely say “no basketball shoes”, I will say that you better know what you’re doing with them and know what to wear them with. They’re generally pretty bulky and command a lot of attention. If done wrong (like wearing them with jerseys/ball shorts off the court), you will look juvenile.
Avoid dirty shoes. There should be a clear distinction between the sneaker you wear for style, and the ones you play sports in. This goes double for all white sneakers. For all white sneakers you should have a weekly routine of cleaning them.
Other Sneaker Styling Tips
There are a few general things you can do with most sneaker styles to step it up. Ankles are your friends. You want to wear no-show, low profile socks (or if sweat’s not a problem for you, just forego socks altogether). Wear your well-fitting selvedge jeans with a small cuff that sits just on top of your sneaker. If you really want to show off and highlight your sneaks, pinrolling (a how-to) is a solid option. And lastly, joggers are a great way to show your sneakers and expose your ankles, as well.
For the Older Guy
As I get older, my sneaker wearing tends to be less and less, however there is still a place for them (and a necessary addition) in every man’s wardrobe. The key to sporting sneakers as you get older is keeping it simple. Going with the bolder colors and designs will make you look like the old guy trying to look young.
Find sneakers with 1-2 colors tops, or even unbranded sneakers that aren’t littered with logos. Jack Purcell and Stan Smith styles are perfect for finding understated, stylish sneakers.
John’s sneaker of choice.
Sometimes you just gotta be brave and go with the short shorts.
Custom Air Max in Marvin’s collection.
Unique shirt perfect for summer