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While some people wish never to recall early 2000s trends, to this day my inner pre-teen clings to the skirt-over-jeans look. Protest all you want, but there’s something so right about Ashley Tisdale in a sequin mini skirt and matching ballet flats, bridged by baggy boot-cut jeans.
The Y2K trend has gradually returned to mainstream fashion over the last few years, but it remains as polarizing as the skinny jeans debate (which is also turning on its head, by the way). Our cultural consensus swings from skirts-over-jeans being cool to it being a total layering faux pas. But as seen with this year’s capri pants renaissance, it’s often the most divisive trends that make the best outfits.
The fall/winter 2024 runways proved its sartorial power, with Paloma Wool and Conner Ives pairing bubble skirts with pants, and Marques’ Almeida styling a mini dress on top of wide-leg jeans. For spring/summer 2025, Chopova Lowena and Diesel’s runways were masterclasses in double-denim looks, while Bottega Veneta previewed midi skirts over pants, too.
Besides being designer-approved, wearing a skirt over jeans also has practical benefits. The additional layer extends the wear of your summer skirts, keeping you warmer than tights. By blending feminine and flowy styles with casual bottoms, you can transform both items for any occasion, from the office to a night out.
For tips and inspiration for this nostalgic layering hack, scroll on to discover the four ways I’m styling skirts over jeans this fall.
How To Wear A Midi Skirt Over Jeans
Start with a midi skirt over jeans if you’re dipping your toe into the trend: The longer length allows for more styling freedom. I was inspired by Chopova Lowena’s pleated skirt styling and paired a knee-length kilt with oversized jeans for this off-duty ‘fit. While the outfit would have been pretty classic without the jeans, the added layer gives it the perfect laid-back vibes for casual weekend plans.
How To Style A Skirt Over Printed Jeans
Print-clashing can be daunting but thanks to the eclectic styling of this trend, bold pattern choices work well. Here, I paired a Marine Serre tartan mini skirt that I got from Depop with my faithful leopard-print jeans to achieve a rebellious schoolgirl look. Keep it simple with neutrals everywhere else to avoid the existential crisis vibes.
How To Style A Mini Dress Over Jeans
I know, I know: A mini dress isn’t technically a skirt — but tell me this doesn’t have the same indie-inspired impact. I love this party dress from the Turkish brand Maksu, but rarely have an opportunity to wear it. By adding jeans and a motorcycle jacket, I can dress it down for various occasions and wear it more often throughout the year.
How To Wear A Skirt Over Metallic Jeans
This combination of a black mini with metallic pants proves a skirt over jeans can be dressed up, too. By styling with dark neutrals throughout the rest of the outfit, you can ensure your jeans (and you) will be the star of the show. Pair with pointed-toe shoes to elevate the look.
Like what you see? How about some more R29 goodness, right here?
How Editors Style Barrel-Leg Jeans For Fall Looks
