For the record, I am all for the resurgence of Y2K fashion. Ballet flats! Tracksuits! Baguette bags! But when I started to hear that people were wearing the dress-over-jeans trend again, my first thought was, respectfully, nah. All I could picture was a Disney Channel red carpet where way too many layers reigned supreme—but as it turns out, fashion girlies have given the early 2000s styling trick a chic, modern update. The new way to wear a dress over jeans is to play with proportions and refresh old pieces. That old party dress that you've been waiting for an excuse to wear again? Give it new life over a pair of baggy jeans. Your crochet dress from Euro Summer? Don't pack it away just yet—you can layer it over your favorite wide-leg jeans for an unexpected twist.
So what's the key to making the dress-over-jeans combo work? It's all about selecting the right dress to layer. I personally <3 dramatic, oversized silhouettes that combine airy skirts with wide-leg styles, but you can def put together sleek, tailored ensembles when wearing dresses over jeans, too. Ahead, you'll find tons of dress-over-jean outfit ideas directly from street style stars, as well as tips for taking your fave spring and summer dresses into fall.
A Babydoll Dress With Cuffed Denim
You might think a voluminous babydoll dress would have to be paired with skinny jeans for contrast, but you thought wrong! I'm obsessed with the unexpected combo of this short, swingy dress with relaxed-fit jeans and dadcore sneakers—and if your dress is sleeveless, you can always layer it under a sheer turtleneck to take it into fall.
Shop the Babydoll Dress with Cuffed Jeans Look:
Lulus Floral Babydoll Dress
Pistola Ryder High Rise Cuffed
ASICS GT-2160 Sneakers
A Long T-Shirt Dress With a Peek of Boot-Cut Jeans
Best way to spice up a roomy cotton T-shirt dress? Add some slouchy jeans to peek out from under the hem. And forget what you may have heard about needing to wear delicate, minimalist shoes with your dress-and-jeans 'fit, 'cause these lug-sole leather boots look pretty badass, no?
Shop the T-Shirt Dress with Boyfriend Jeans Look:
A Slitted Shirt Dress With Wide-Leg Jeans
For an office-approved dress-and-jeans lewk, try an oversized shirt dress with straight-leg jeans. The flowy silhouette of this one from The Frankie Shop will keep things light 'n' breezy, while the generous splits at the hem means you'll have plenty of movement (and plenty of opportunities to show off your denim!). The cherry on top: those sweet lil strappy sandals.
Shop the Shirt Dress with Full-Length Jeans Look:
The Frankie Shop Avery Fluid Shirt Dress
Charles & Keith Meadow Strappy Toe Ring Sandals
A Romantic, Tiered Dress With Baggy Jeans
Wanna add some volume? Keep the full-skirted maxi shape of a longer tiered dress with some wide-leg jeans worn underneath. Add some cute Mary Jane flats for some extra whimsy.
Shop the Tiered Midi Dress with Two-Tone Jeans Look:
Citizens of Humanity Ayla Baggy Crop
A Denim Shirtdress With Blue Jeans
IMO, you can never go wrong with a Canadian tuxedo, and no, your denim dress doesn't have to match your jeans. A dress with buttons down the front gives you lots of fun options to play with, but I love how the look above makes the dress into more of a jacket here and allows the T-shirt beneath to peek through.
Shop the Denim Dress with Sailor Jeans Look:
Wash Lab Denim Shirtdress
Franco Sarto Flexabooty Boots
A Mesh Maxi Dress With Slouchy Jeans
If your go-to going out 'fit consists of a crop top and slouchy jeans, why not add some visual interest by layering a mesh maxi over it? This sheer dress can instantly take your look from *yawn* to chic, and the retro sneaks still keeps it feeling casual, if that's the vibe you want.
Shop the Mesh Dress with Slouchy Jeans Look:
Garage Slouchy Jean
An Asymmetric Dress With Ripped Jeans
The modern version of a tunic dress and skinny jeans? An asymmetrical dress and baggy jeans. Rather than just giving a peek of denim on the bottom, this look lets you show off plenty of jean thanks to the cut of the skirt, and IMO, those chunky black boots really up the cool-girl factor.
Shop the Asymmetrical Dress with Ripped Jeans Look:
Good American Good '90s Jeans
A Puff-Sleeve Dress With Straight Jeans
If you're playing with a lot of volume on top (we're talking bubble sleeves, empire waist, full skirt, etc.) and you don't want the extra bagginess of a wider leg pant, you can keep things feeling balanced with some sleek straight-leg jeans and polished booties.
Shop the Puff-Sleeve Dress with Straight Jeans Look:
Moon River Woven Textured A-Line Dress
Reformation Cynthia Straight Jeans
Dolce Vita Glamor Boots
A Cardigan Dress With Low-Rise Jeans
Yep, even Gigi Hadid is hopping on the dress-over-jeans trend and doing it in a very approachable way: with the tried-and-true button-front sweater dress. I love the versatility of this combo, since you can button your dress all the way, leave it unbuttoned from the naval down (like Gigi chose here), or leave it totally unbuttoned—the choice is yours.
Shop the Cardigan Dress with Low-Rise Jeans Look:
RE/DONE Loose Long Jeans
Sam Edelman Bianka Slingback
A Slip Dress With Boot-Cut Jeans
Sorry to say that the COS Striped Sequined Slip Dress worn here is almost out of stock (womp), but really, any '90s-inspired silky slip dress will help you nail this look. I suggest choosing one made with lightweight material and featuring a deep side slit for movement, and then adding a subtly flared leg for a chic, breezy finish.
Shop the Slip Dress with Boot-Cut Jeans Look:
JW PEI Alivia Gold Metal Heel Sandals
A Sheer Dress With Raw-Hem Jeans
Ever see those sheer, mesh dresses and think, "Uh, how are ppl wearing these?" Ta-da! Layering jeans under the peekaboo fabric lets ya feel a bit more covered up than you might otherwise, and you can choose how much coverage you want up top based on what you wear underneath. Oh, and peep one of fall's top shoe trends: leopard-print flats!
Shop the Sheer Dress with Raw Hem Jeans Look:
Paige Anessa Wide-Leg Jeans
Zara Animal Print Ballet Flats
A Crochet Dress With Wide-Leg Jeans
Who said crochet dresses could only be used as swimsuit cover-ups? Even though this option is a bit more tailored, it'll still give you plenty of flexibility and movement with its open, airy design—and when worn with flared jeans, you can really lean into the '70s-inspired aesthetic.
Shop the Crochet Dress with Wide-Leg Jeans Look:
Everlane The City Boot
A Mini Dress With Relaxed-Fit Jeans
Now this is how you transition your mini dresses into fall (especially if tights aren't your thing!). I'm very into the fitted waist and flowy skirt of this mini, which balance so nicely with those wide-leg jeans.
Shop the Printed Mini Dress with Relaxed Jeans Look:
Levi's Ribcage Wide Leg Jeans
Beckett Simonon Savannah Booties
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Each of our shopping articles adheres to the 15 Percent Pledge and includes products for all sizes. These dress-over-jean outfits were chosen based on style and functionality to put together this shoppable list of the very best for you!
Corinne Sullivan is an Editor at Cosmopolitan, where she covers a variety of beats, including lifestyle, entertainment, relationships, shopping, and more. She can tell you everything you need to know about the love lives of A-listers, the coziest bedsheets, and the sex toys actually worth your $$$. She is also the author of the 2018 novel Indecent. Follow her on Instagram for cute pics of her pup and bébé.
