The 11 Coolest Outfits With Ripped Jeans, Hands Down

I tend to gravitate toward tailored, polished pieces so you might be surprised to hear about one of my recent fashion obsessions: ripped jeans. I tie it to both the more casual, comfortable wardrobe I’ve been adopting this year, the grunge-inspired fashion unfolding on TikTok, and my general love of all things ‘90s, but there’s no denying that I can’t get enough of the trend. Plus, it’s been everywhere on the fashion scene recently, so I’ve been inspired by all of the cool ways insiders are wearing it right now.

Whether worn with the fall sweater vest trend, chunky loafers, a knit polo, or a structured blazer (as I’ve been styling them), there are plenty of cool ways to wear outfits with ripped denim this season. Ahead, see my favorite ways to style the coolest denim trend of the moment and scroll to the end to see how I’m wearing them myself.

Arguably one of the biggest trends of the season, a sweater vest is the ultimate piece to pair with the #1 denim trend of the moment.

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This outfit is all about creative ways to style your basics. Simply layer an oversize button-down top under a sweater here.

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Now here's exactly how to style the most popular boot trend of the season. There are honestly endless ways to wear them but this outfit is foolproof.

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If you buy a knit this season, make it a ribbed one. Seen in the collections of brands like Bottega Veneta and Dion Lee, it's a very on-trend way to wear sweaters this season.

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I hate to be partial but I just can't get enough of the leather trench trend. It works with so many pieces in your wardrobe and ripped jeans are definitely one of them.

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You honestly can't beat a jeans and sneakers combo and this is the freshest way to wear them.

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Is there anything I love more than a denim-on-denim look? Not really.

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If you've been ready to hop on the chunky loafer trend, this outfit is a cool study in the exact way to wear it. Just add a knit and ankle socks to your ripped denim.

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Collared polo tops are trending hard, so it's no surprise we're seeing them pop up with this denim trend at the moment.

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It doesn't get more simple or chic than jeans and a tee and this is the coolest way to pull it off.

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I told you I'd be including one of my outfits wearing the ripped denim trend and this is it. I love the idea of balancing the grunge-inspired jeans with a more structured piece like this tailored blazer.

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Next, shop 25 cool fashion finds I’m obsessing over right now.