The Anti-Skinny Jean Trend That's Back and Cooler Than Ever

I tend to gravitate towards 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 knitted 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.

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With a sweater vest:
(Image credit: @zaraynaf; Pictured: Zara jeans; Prada shoes)

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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With an oversize button-down:
(Image credit: @izzydilg; Pictured: Zara jeans)

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

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With chunky Chelsea boots:
(Image credit: @lefevrediary; Pictured: Tamara Mellon boots)

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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With a ribbed sweater:
(Image credit: @emmaleger; Pictured: Zara jeans; Dior bag)

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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With a leather trench:
(Image credit: @aimeesong; Pictured: Privacy Pls top; L'Academie jeans)

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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With sneakers:
(Image credit: @tylauren; Pictured: Louis Vuitton jacket; Levi's jeans; Nike sneakers)

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

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With a denim jacket:
(Image credit: @emmaleger; Pictured: Zara jeans; Vehla sunglasses; Prada bag)

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

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With chunky loafers:
(Image credit: @pernilleteisbaek; Pictured: Chanel shoes)

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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With a tee:
(Image credit: @javiera; Pictured: Fashion Nova jeans)

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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With a structured blazer:
(Image credit: @kristenmarienichols: Pictured: A.W.A.K.E MODE Crepe Peplum Blazer; Agolde jeans; Manolo Blahnik heels)

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, see the key trends for autumn winter 2020.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear where she oversees luxury content and Who What Wear Weddings, and covers fashion content including the designer market, runway reporting, and seasonal trends. She also writes columns including The Luxury List, Investment Portfolio, and What’s Good. Prior to Who What Wear, Kristen held positions at Allure and Rodarte. She studied Art History and Business at the University of Southern California and currently resides in New York.