4 Comfortable Fall Denim Trends to Look Forward to Wearing

Call me crazy but I actually miss wearing jeans. Obviously it's been ridiculously hot as of late, but I also am just tired of feeling like I'm constantly enveloped in jersey knit. I long for something crisper and a little more dressed up, yet still familiar. That's why I've decided not to abandon denim again as I did back in March when lockdowns began. But for fall 2020, I'm definitely buying fewer rigid, straight-leg styles and more loose, relaxed, stretchy styles.

Given the aforementioned limitations I'm placing on my denim shopping this fall, I've narrowed the options way down, to four specific styles, all of which are considerably more comfortable than many jeans on the market. And after narrowing them down, I noticed something fun: Each style corresponds with the major denim trend that a past decade is known for. 

So with that, scroll to shop fall's four most comfortable denim trends, that originally date back to the '70s, '80s, '90s, and '00s. 

From the '00s: Distressed Jeans

Ripped jeans are one of the most surprising trends to return this year, but based on how many celebrities and influencers are wearing them, it can't be ignored. I, for one, haven't worn distressed denim much since the 2000s, but I'm very tempted to purchase a pair. This time around, go for more subtle distressing and a slouchy silhouette (as opposed to skinny jeans).


(Image credit: @claire_most)

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From the '90s: Skater Jeans

Skater jeans is a fun trend that coincides with the overarching grunge theme on the F/W 20 runways. This long and baggy style is comfortable for obvious reasons, and actually looks even cooler with similarly baggy pieces, so feel free to embraced the all oversized everything look when wearing them.


(Image credit: @champagnemani)

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From the '80s: Pleated Jeans

Think of pleated jeans as mom jeans 2.0. Featuring a high waist and often a tapered leg, pleated jeans are surprisingly flattering and easy to wear, in addition to being nice and roomy (AKA comfortable). 


(Image credit: @raeannlangas)

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From the '70s: Flared Jeans

As is the case every few years in fashion, the '70s are back. And the return of the '70s couldn't be possible without the adjacent return of flared jeans. My best advice for making it work? Opt for a high-waisted style and wear heels (even just a low heel is better than flats with flares). Last but not least, definitely choose a pair with even just a hint of stretch to keep things comfortable.


(Image credit: @annelauremais)

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Next up, the 6 best basics to wear with jeans this fall.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.