When In Doubt, Pull on a Pair of Chucks

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In this men’s style guide, get inspired with a roundup of Converse high top sneaker outfits for guys, and shop stylish Converse Chuck Taylors and Chuck 70s…

The great thing about a classic clothing item is you can make it as modern and personal to your style as you want. The only limit is your own creativity (and contents of your wardrobe, I suppose).

Take Converse high top sneaker outfits, for example.

Sure, you could go full Richie Cunningham from Happy Days, pairing the sneakers with high-rise denim, letterman’s jacket, and James Dean hair. That is, if a throwback Americana vibe suits you.

But that’s not your only option! Not by a long shot. There’s plenty of ways to wear Chucks in 2024 that feel…well, totally 2024.

So, if you’ve been holding off from adding these timeless sneakers to your footwear rotation because you just weren’t sure how to wear them in a way that feels like you? Well, read on.

First up? Your high top options.

What’s the difference between Chuck Taylors and Chuck 70s?

When you think Chucks, your mind probably goes to the Converse Chuck Taylor All Star. And sure, this sneaker icon absolutely deserves a spot on Sneaker Mt. Rushmore, but it’s not your only option.

Converse Chuck Taylor side-by-side with Converse Chuck 70s

The Converse Chuck 70 are a sturdier shoe than the more familiar Chuck Taylor, with added padding and arch support. So if you’re looking for a shoe you can wear all day, you may want to splurge on this higher priced pair.

“Splurge” being a relative term, as both styles ring up under $100 — Chuck Taylors go for $65 while Chuck 70s are $90.

To be clear, there’s no right or wrong answer here. One shoe is not more stylish than the other. It’s simply a question of, which Converse sneaker is right for you?

If you’re wondering who’s wearing what, here’s a key tell. The sole of the Chuck 70 is a cream color, while the All-Star sole is white.

Get inspired with 7 Converse high top sneaker outfits for guys:

man standing on the street in front of a car wearing a short-sleeve patterned shirt over a long-sleeve shirt with dark pants rolled up at the ankle with black converse all star sneakers — @ryanculligan

Roll your cuffs to show off your sneakers

These high-tops have become a staple in so many guys’ wardrobe because, like a style chameleon, they can blend seamlessly into any outfit.

Here, the sneaker’s classic design offers a fashionable finishing touch to a laid-back look that could be called “California workwear.”

young man standing on a building stoop wearing a red t-shirt with ripped jeans and white converse all star sneakers, converse high top sneaker outfits — @jabarisandifer

Coordinate your shoes with your tee

While basketball players were the first to wear the sneaker, Chucks have moved off the court and into the streets.

For an easy off-duty look, wear a white pair light wash jeans and a top that picks up the red detailing in the sneaker.

NBA draft pick not required.

man standing on a staircase wearing a white t-shirt with teal pants and converse chuck taylors — @smaclo_dera

Use your Chucks to ground a colorful outfit

Maybe teal’s not your thing, but why not wear your neutral-hued Chucks with the brightest thing you own? Ground a colorful pair of pants or shirt with a subtle pair of sneaks in black, grey, navy, or white.