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Evening Standard
Evening Standard
Lifestyle
Saskia Kemsley

I grew up in the Noughties, here’s how to wear dresses with jeans in 2025

If I were to describe sartorial trends from the last five years in a single word, it would be: textural.

Whether it’s pairing tulle skirts with baby tees à la Carrie Bradshaw, inception-accessorising by clipping fuzzy Labubus to cult handbags, or using safety pins to reconfigure vests, long sleeves and maxi dresses into something almost sculptural, Gen-Z (and those of us hovering on the cusp of Zillennial) are more interested in wardrobe customisation than ever before – despite, or perhaps in spite of, the endless churn of microtrends.

The single best, budget-friendly way to add textural intrigue to any outfit? Layers. Always layers.

Experimenting with autumnal fashion (Saskia Kemsley)

Think vests under tees, tees under slip dresses, leg warmers over leggings, lace slips over cotton ones – and yes, the reason you’re here: dresses worn over jeans or trousers. Once the mercury drops, this is a styling trick that makes both practical and aesthetic sense.

(Comp via Getty Images)

The look is hardly new. In the early Noughties, it was ubiquitous. Ashley Tisdale on a Disney red carpet, Anne Hathaway promoting a Hollywood film, Mischa Barton running errands in LA, even The Row founders Mary Kate and Ashley in boho styles. But the 2025 iteration has a distinct editorial edge.

Fashion’s usual suspects have been setting the stage. In Tokyo and Seoul, trouser-skirt hybrids have long been a street style staple. In Copenhagen and Paris, Scandi minimalists pair crisp white shirt dresses with wide-leg jeans, or bias-cut silk slips over tailored trousers, leaning into a sort of architectural elegance. The effect is no longer chaotic, but coolly composed.

(HypeBae via Instagram)

And contrary to popular belief, there’s no “correct” hemline to attempt the look with. Mini, midi, maxi –they all work, depending on the textures you’re building with. A thigh-skimming baby doll over slouchy denim feels playful, almost nostalgic, while a tea-length lace dress with straight-leg jeans veers into romantic grunge. Full-length bias silk over puddle pants, meanwhile, is sleek, grown-up and strangely subversive.

Office lift selfie, sporting a controversial babydoll dress and bootcut jeans ensemble (Saskia Kemsley)

The trick lies in proportion and texture. A floaty dress works best with more structured denim to ground it. Heavier fabrics like velvet or jacquard need fluid trousers beneath to soften them. If you are nervous about looking like you’ve raided a 2006 Tumblr archive, accessories will prove to be your saving grace. For footwear, think sharp ballet flats, stompy loafers, or pointed kitten heels rather than knee-high Converse. Keep bags modern: crescent shapes, top-handle minis, or slouchy leather totes.

In 2025, dresses-over-jeans isn’t about irony. It’s about creating texture, adding dimension, and proving that, sometimes, two wrongs really can make a right.

Below, I’ve curated a selection of the best dresses to wear over jeans so that you can get experimental with your autumn/winter style.

Shop now

Reformation Cleodora Dress

The Cleodora has all the makings of a grown-up slip: languid silk, romantic ruching, the sort of neckline that works with both ballet flats and statement earrings. But in 2025, its real magic lies in layering. Try it over slouchy wide-leg denim with pointed kitten heels for an editorial edge.

Buy now £248.00, Reformation

JAG Pure Linen Button Front Mini Shift Dress

Clean, crisp, and unashamedly minimalist, this linen shift from JAG feels like a summer holiday essential – but it doesn’t need to be confined to Santorini sunsets. Worn open over wide-leg denim, it doubles as a cropped duster coat / eccentric layering piece.

Buy now £150.00, M&S

Collusion sheer mini dress in sheer pink and black acid gingham

Collusion’s acid gingham mini offers an affordable entry point into the trend. Its sheer finish makes it prime for layering: slip it over baggy jeans with a visible bralette for a nostalgic nod, or lean into Gen-Z grunge with cargo trousers and stompy boots. The key is contrast: offset the sweetness of pink gingham with something harder underneath.

Buy now £24.99, ASOS

We The Free In This Groove Mini Slip

This slinky Free People number toes the line between boudoir and streetwear, which is exactly why it works layered. Slip it over cargo trousers with platform sandals for a Y2K look, or refine it with tailored black slacks and ballet pumps for something altogether sleeker. The cut skims without clinging, making it an ideal canvas for textural play. Plus, it’s available in every colour under the sun.

Buy now £108.00, Free People

Reformation Arella Denim Mini Dress

Think of this structured, perfectly pleated denim mini from Reformation as your shortcut to double denim without ever feeling matchy-matchy. Pair them with some bootcut jeans in contrasting denim with some all-weather pumps for the ultimate autumnal ensemble. When the weather drops below zero, simply pop a turtleneck underneath.

Buy now £74.40, Reformation

Desigual Dress designed by Mr. Christian Lacroix

As collaborations go, Christian Lacroix x Desigual is a maximalist’s fever dream. This graphic print mini is bold enough on its own, but paired with denim it becomes an art project. Let the dress be the focal point – straight black jeans and simple Mary Janes will stop it overwhelming, while a sharp-shouldered blazer adds structure.

Buy now £72.50, Desigual

Damson Madder Raphi lace midi dress – coffee

Damson Madder knows how to do a modern romantic, and the Raphi is proof. Its coffee lace and sheer paneling feel decadent, but paired with wide-leg jeans the mood shifts into something more undone, almost grunge-romantic. Add flat Mary Janes or stompy loafers to keep it wearable, and layer a longline coat over for autumn.

Buy now £100.00, Damson Madder

Nobody’s Child White Broderie Angalise Claudia Mini Dress

White broderie anglaise is a summer staple, but in 2025 it can be surprisingly adaptable. Over dark denim, the Claudia mini becomes crisp, graphic, almost preppy. Pair it with straight-leg jeans and slingbacks for office-adjacent polish, or slouchier denim and flat sandals for a festival spin.

Buy now £60.00, Nobody’s Child

Reclaimed Vintage lace mesh maxi layering dress in yellow

This Reclaimed Vintage mesh maxi is designed with layering in mind, which makes it the ultimate Y2K-meets-2025 piece. Its sheer lemon hue works over anything - black flares for maximum contrast, tonal pastel jeans for a softer touch. Cinch with a belt if you want definition, or let it float free for that ethereal, barely-there energy.

Buy now £25.99, ASOS

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