The 11 Coolest Outfits With Ripped Jeans, Hands Down

last updated 16 November 2020

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.

outfits-with-ripped-jeans-289961-1604632629218-main — With a sweater vest:

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.

Shop the look:

Ksubi

Playback Kut Up Distressed High-Rise Straight-Leg Jeans

Mango

V-Neck Knit Gillet

outfits-with-ripped-jeans-289961-1604632717426-main — With an oversize button-down:

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

Shop the look:

Zara

Ripped Mom Jeans Trf

Totême

Capri Cotton-Poplin Shirt

outfits-with-ripped-jeans-289961-1604601246961-image — With chunky Chelsea 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.

Shop the look:

Grlfrnd

Devon Distressed High-Rise Straight-Leg Jeans

& Other Stories

Chunky Leather Chelsea Boots

outfits-with-ripped-jeans-289961-1604632498955-main — With a ribbed sweater:

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.

Shop the look:

Still Here

Childhood Distressed High-Rise Straight-Leg Jeans

Bottega Veneta

Ribbed-Knit Sweater

outfits-with-ripped-jeans-289961-1604601245281-image — With a leather trench:

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.

Shop the look:

Raey

Dad Ripped Boyfriend Jeans

Mango

Faux-Leather Trench

outfits-with-ripped-jeans-289961-1604636299465-main — With sneakers:

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

Shop the look:

Zara

Slim Fit Jeans With Rips

Veja

Rio Branco Leather-Trimmed Suede and Mesh Sneakers

outfits-with-ripped-jeans-289961-1604632330851-main — With a denim jacket:

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

Shop the look:

ASOS

Recycled High Rise Slouchy Mom Jeans

Zara

Oversized Denim Jacket

outfits-with-ripped-jeans-289961-1604632767263-main — With chunky loafers:

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.

Shop the look:

L'Agence

High Line Cropped Distressed Skinny Jeans

Mango

Leather Heel Loafers

outfits-with-ripped-jeans-289961-1604636179623-image — With a tee:

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

Shop the look:

Grlfrnd

Karolina Cropped Distressed High-Rise Skinny Jeans

Ninety Percent

Linen-Jersey T-Shirt

outfits-with-ripped-jeans-289961-1604641749224-main — With a structured blazer:

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.

Shop the look:

RE/DONE

90s Distressed High-Rise Straight-Leg Jeans

Arket

Belted Blazer

Next, see the key trends for autumn winter 2020.

Explore More:

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.