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How To Wear Dresses Over Jeans And Not Look Like A 2004 Disney Channel Star

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This might get me canceled, but idgaf. I love dresses over jeans. They were never a fashion faux pas!  The cultural zeitgeist might love all things Y2K now, but real ones remember the Internet shaming early aughts fashion lovers. This was during the Golden Age of Twitter, long before today’s style influencers Bella Hadid and Hailey Bieber were known as anything other than nepo babies. (Which in ‘00s speak means socialites). Plaid, side ponytails, and flower crowns were in. Dresses over jeans? Tacky and outdated. 

The Internet changed its mind and now dresses over jeans are cool again. Well, I call bull-freaking-shit. Can we puh-lease stop with cyclical trends? Like, dresses over jeans are a forever staple, not another temporary cool aesthetic to try on and then throw away afterward. You can keep that energy for juicy couture sweats and duck nails, thank you. 

A boho dress over boot-cut jeans was never the dumpster fire the haters proclaimed it to be. Frankly, most Y2K fashion moments were iconic and deserved praise. And yeah, you can say early 2000s fashion is having its moment ‘cause that’s what people are wearing, but what happens when the collective decides, “Hm, actually, that babydoll dress with those baggy jeans is hideous”? What then, huh? I’m just supposed to stop wearing my fave dress and jean combo and instead dress like a Martha Stewart catalog?


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Wearing understated neutrals and minimalistic accessories to show off my non-existent wealth? Embracing #quietluxury? I’m sorry, but no. Like, is it cute, classic, and chic? Of course; perfect fits for Target runs and those Molly-Mae-like aesthetic coffee pics. But daring, bold, or trendsetting? I laugh. 

It’s easy to dress like you’re worth a thousand bucks but for a dress-over-jeans ensemble. It requires style and the ability to accessorize. Because it’s ugly, really, but in that alluring way that makes you stop and think, “Damn, she low-key ate that.” You get the same feeling when you see someone wear funky patterns and mismatched clothes that shouldn’t go together but definitely do. It’s the chaotic pairing of clothing that feels clownish, but in actuality, looks stylish and original. Which is rare to come by these days when we’re all just carbon copies of one another. 

Dresses over jeans require effort and more importantly, creativity. It’s easy to get it wrong, hence why few wear it and even fewer know how to. The wrong color jeans, accessory, or shoe will have you lookin’ frumpy, baggy, and all over the place. And that’s never the vibe. But coordinating the look isn’t hard. Most of us are just scared to look like a 2004 Disney Channel actor on their first red carpet, which, like, fair. But when in doubt, look to a Y2K trendsetter whose style — back then and now — is revered: quintessential girl-next-door Katie Holmes. 

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No one does dresses-over-jeans (or any early aughts look, really) better than Ms. Joey Potter. Something about the choice of dresses and jeans and the accessories plus the shoes just hits. Even the most hating hater can’t deny she slays every. single. time. So, if you want to replicate the style, start with Katie.

Or your best friend, TikTok. If there’s one thing the TikTok girlies know how to do, it’s make anything aesthetic.

Follow content creators doing GRWMs donning a babydoll mini dress over light wash mom jeans, finished with chunky white sneakers and an over-the-shoulder handbag.

Fit Inspo Number 1


Shop Now

Avidlove Women’s Lingerie Lace Babydoll Dress, $19.99

Oversize Mom Jeans, $46.20

Skechers Women’s D’Lites Fresh Start Sneaker, $48.30 – $59.99

JW PEI Women’s Joy Shoulder Bag, $89.99

Pinterest is there too with fits like: 1) a midi black frill dress over baggy jeans, held together by a silver chain belt and completed with black ballet flats and a leather clutch and 2) light blue flare jeans paired with a white sundress, sneakers, and a messenger handbag.

Fit Inspo Number 2 


Shop Now

Ruffle Trim Slipdress, $84

Women’s Baggy Dad Jeans, $108

Alloy Gold Waist Chain Belt, $15.99

Felicia Luxe Flat, $52-$150

Nic Faux Leather Clutch, $75

Fit Inspo Number 3 


Shop Now

Flare Low Jeans, $29.99

Dokotoo Womens Summer Dresses, $33.99

SCRUFFY DOG Canvas Messenger Bag, $39.95

Gola Elan Sneaker, $110

Alright, I think I’m done here. You have more than enough style inspiration and if  you want more, go read this. Or Google. I’m not a free 99 stylist. Bye. 

Mel Curry
Mel Curry
Mel Curry is a pop culture writer who spends way too much time watching Love Island and drinking caffeine. You can catch her strolling down the streets of New York looking for her next adventure—or, err gig. Her work has appeared in Cosmopolitan, InStyle, Women's Health, and ya daddy's dms. Follow her on IG @melaniercurry