Fashion People Are Wearing Dresses With Jeans—32 Styles to Shop the Look

If you take one look at social media right now, you’ll be inundated with content from fashionable folks trying different trending looks. While keeping up with the latest outfit ideas can be fun, it can also get overwhelming. As a fashion editor, I’m here to alleviate some of that stress. Since it’s my job to stay updated on fashion, I spend a lot of time online. While browsing through social media, I noticed fashion people are wearing jeans with dresses.
For all of you Y2K-fashion lovers, you know this outfit combo isn’t new. That said, it’s definitely been on the rise recently. For your shopping pleasure, I handpicked an array of jeans and dresses perfect for mixing and matching to nail this look. Keep scrolling to uncover my selections for creating this throwback outfit for yourself.
Shop Jeans
Paige makes plus-size jeans you can shop exclusively through Anthropologie.
This pair is slightly cropped for those that want their shoes to show.
If high-rise jeans made breathing more difficult, try these trusty Levi's. They have a classic wash and cut with a mid-rise waistband.
While these have a price tag that falls on the higher side, it's worth it for this chic jet-black wash.
Cropped wide-leg jeans aren't going anywhere anytime soon.
These shorts would complement any dress well, especially a sheer-knit dress.
Shop Dresses
Leave this dress buttoned only halfway to maximize styling it with jeans.
Throw this one on over a black tube top and blue jeans for an updated take on a classic Y2K style.
This beauty is from the limited-edition Daisy Jones & The Six Collection.
Next, 30 Anthropologie and Free People Styles Daisy Jones Would Approve Of

Chinazor "Chichi" Offor is a Georgia-born, Los Angeles–based associate editor who relocated from Brooklyn, New York, and joined Who What Wear's West Coast office in 2022. At WWW, she utilizes over 10 years of editorial experience to dish out shopping advice to the masses and analyze key pop-cultural moments. Chichi previously worked at Refinery29, where she helped revolutionize the brand’s plus-size and inclusive fashion coverage. In her spare time, she’s keeping up with the latest movie releases, enjoying a relaxing day at the spa, or obsessing over her latest ADHD-fueled hyperfixation (e.g., Jesse McCartney's underrated career, the negative effects of bicoastal intellectual elitism, and Gen Z’s loneliness epidemic). You can find her online @thechichio on Instagram.
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