STYLE

6 ways to style dresses over jeans for autumn

The Y2K fashion fave – dresses over jeans is back! Cool-girl-chic and whimsical, these 6 fits are a must-try.

PUBLISHED: OCT 10, 2025

6 ways to style dresses over jeans as the controversial Y2K trend makes a comeback for autumn

We’re here for the dress over jeans revival

Every once in a while, a trend rears its head that is well and truly divisive (bubble skirts! clogs! capri pants!). If you’re brave, you’ll indulge — but it pays to get some expert advice before you start dabbling.

For autumn, that trend is … dresses over jeans. Yes, if you lived through the ‘90s or 2000s, the very thought of this look may make you shudder. But, if you think about it … it’s super practical! As the weather cools down, we’re all looking for new ways to layer without getting in a styling rut. Jeans + a dress = unexpectedly on-trend cold weather dressing.

There are also plenty of variations on this look. For some, it’s all about an asymmetric maxi dress with just a sliver of jean hem showing above the shoes. For others, it’s about finding new life out of an eccentric, puffball summer dress (very Molly Goddard) by layering it up for winter. And, for others, it’s a nostalgic way of tapping into the boho trend, which is currently on everyone’s FYPs.

Below, we round up six sure-fire ways of styling dresses over jeans, with plenty of outfit inspo while we’re at it. Thank us later!

Sheer dress and jeans

If you’re hesitant about how to approach the jeans + dress combo, look no further than a sheer dress and light-wash, baggy denim. This combo can be paired with a pair of statement flats for warmer days and a long Penny Lane coat for a more boho feel. Here, you can play about with the texture of the dress: a fine gauge, see-through knit or a sheer, lacy, voile. Depending on the type of sheer dress, you can dress this one up with a clutch and jewellery to be a suitable date or evening wear look.

Mini dress and jeans

This is the most Y2K way of approaching this look, tapping into how the trend was styled back in the day by teen icons like Ashley Tisdale. Grab a light or mid-wash pair of jeans and opt for a more mid or wide-legged trouser cut. Then, opt for a true aughts mini dress with either a babydoll or plunging v-neck neckline. Pair with a set of motorcycle boots, and a hobo bag, maybe even a faux-fur jacket over the top, and you'll be looking like Lindsay Lohan in 2008 … aka fabulous.

Slip dress and jeans

Another great way of styling jeans is with a slip dress, in either a maxi, midi, or mini length. The key is to size up, or to opt for a baggier slip dress in your wardrobe, so that it can slip over your jeans. You can even layer a further item under your slip, such as a crisp, contrast colour tee-shirt. We’d recommend (again!) keeping with the mid-leg and mid-rinse jeans styles currently trending, and accessorising with either a pair of ballet flats or a pair of loafers. This goes well with a more cropped jacket, such as a bomber or varsity style, for a great daytime look.

Empire waist dress and jeans

Ready for some inventive office wear? The empire waist dress, generally in a shorter length and in white, pairs well with a stiffer, organic, dark-wash denim jean and can pair with stiff leather loafers or even clogs for a work look (if you have a more flexible office dress code, of course!). You can also dress it down with trainers and/or distressed denim.

Puffball dress and jeans

Calling lovers of whimsy! We love a bright, voluminous puffball dress in an eye-catching colour and, preferably, many layers of tulle. These pieces look great when layered over a more casual pair of jeans, bringing the standout look into the daywear space. You can pair with a sleek pair of ankle boots, loafers, ballet flats, or low-profile trainers, depending on your preference.

Asymmetric maxi dress and jeans

If you’re looking for a more sophisticated take on the dress and jeans combo, your best option is sticking to a maxi, asymmetric dress paired with a pair of jeans. The key to this one is trying to stick to as monochrome a colour palette as possible, i.e dark-wash jeans paired with navy dress, black jeans paired with black dress … you get the picture. Pair with some statement silver or gold jewellery (cuffs and bangles are biiiig this season) and slick your hair back in a bun, and you’re good to go.