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).
Shop the Trend
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.
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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).
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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.
Shop the Trend
Next up, the 6 best basics to wear with jeans this fall.
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Light-Wash Jeans Always Look More Expensive When Worn With This Elevated BasicAs seen on Zendaya in Italy.
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Tired of Jeans? We Are Too—Here's What We're Wearing Instead This SpringChic and comfortable.
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7 Ways to Style Your Jeans for Spring That Feel Very 2025Courtesy of the street style set.
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My Most Complimented Everyday Jeans Are on Sale for Just a Few More HoursGrab them now, or pay full price later.
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Rich-Looking Outfits Are the Goal—31 Chic Pieces From the Amazon Big Spring Sale That Fit the BillThese will have you doing a double take.
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I Found a Trove of Cool-Girl Basics From theReplica Store Sale—31 Chic StandoutsThese have closet-staple status.
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It's Here: The 2025 Version of Skinny JeansSpotted on Emily Ratajkowski in NYC.
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35 Incredibly Chic Luxury Finds I Would Immediately Buy If My Salary Tripled TomorrowA girl can dream, right?
