Dresses over trousers? The controversial trend is back

The return of dresses over trousers. Who would have thunk it. I first caught a glimpse of my favourite 1990s trend in a few street style pics from Copenhagen Fashion Week earlier in the year – I gave a nostalgic sigh, but not much more thought.

Then, a few weeks later on the Gucci runway, in the debut collection from new designer Sabato De Sarno: a crystal encrusted, lime green shift dress worn over jeans, with heels and a green snakeskin shoulder bag. Pure déjà vu from my Sex and the City era wardrobe.

As if I needed any further proof of the phenomenon, Alexa Chung has also been reprising the look, posting a picture of herself on Instagram in a pouffy transparent black tulle dress over jeans, along with the defiant caption: “I missed dresses over jeans, sorry if you didn’t.”

It’s official then, the “skouser” trend (not the most elegant neologism, I grant you) is back, should you care to give it another whirl… Or indeed to try it out for the first time.

To be clear, this is not all about wearing dresses or skirts over jeans … It never was. Back in the 90s, wearing slinky evening trousers with a slip dress and a sheer top was the foundation of some of my snazziest going out looks. Incidentally, this turned out to be a godsend on one occasion when I went to the American Bar at The Savoy with my boyfriend (now husband) for Christmas cocktails. I was wearing a smart pair of bootcut pants with a jacquard shift dress and heels as per; but when his “indie boy” ensemble fell foul of the no-jeans dress code, I was actually able to lend him my trousers and still remain perfectly decent (the night of the ladies’ pants has gone down in family history of course – what a keeper!).

Fast forward to winter 2023, model Mouchette Bell, who moved to the other side of the lens after many years as a stylist and fashion director, tells me: “I did really like trousers with dresses the first time round in the Nineties and I am going to do it again. I will wear either very narrow trousers or something that’s more like a pyjama, really it just depends on what makes you feel good, but I do think it’s a cool look.”

I should say that Bell is a walking masterclass in how to layer a vintage jacquard dress or sequin mermaid skirt over jeans – with a thermal t-shirt, and a parka – so that you get a sense of her eclectic, feminine style even in winter months when bundling up is key.

It’s always fascinating when a particular trend comes back into focus; and why it is that it resonates all over again. In its 90s iteration, the irreverent mash-up of genders and genres inherent in wearing a skirt over trousers was rooted in the tarnished glamour and androgyny of “grunge”. Who can forget the iconic image of a bleach-haired, bearded Kurt Cobain on the cover of The Face in a floral frock?

Of course, the rage and rebellion of that provocative stance has a new relevance in gender fluid dressing 2023-style. There was also a strong influence of traditional Indian clothing on 90s Western wardrobes. Think: embroidered tunics over floaty trousers, whether in the elevated designs of Dries Van Noten, or on the high street rails at Monsoon or Whistles; and not forgetting sequin-spangled, DIY “Bhangra Disco” get-ups for East-meets-West club nights. As the fashion conversation becomes more diverse and global, it makes sense that this approach to dressing is now fully in the mix.

Steph Stevens, the stylist and consultant who has worked closely with Alexa Chung over the years, was synonymous with the irreverent, unexpected layered look of dresses/skirts over trousers in her definitive 90s fashion editorials for titles like J17, and Minx (RIP). Why did this style speak to her? “It was fun!” she says simply. “The way I styled the look was quite scruffy and mismatched. It was also a great way to use vintage clothes from different eras that somehow worked together, which translated into a ‘don’t care’ vibe which I loved.”

While Steven’s Nineties signature style was tomboyish and never afraid to push the boundaries, she thinks that the dresses over trousers phenomenon was appealing to a huge number of women at the time, because it allowed them to experiment with pieces they already had in their wardrobe to find a silhouette that worked for them. “It can look so chic and it’s playful, which surely we all embrace,” she says, describing a particular COS shirt as her ideal look.

I’ve got a feeling that the trouser plus dress equation is a very promising solution for the party season. Much as I always want to look good for the festivities, feeling comfortable and not too dressed up to go on the tube are also high up there on my priorities list.

With this brief in mind, I hit the fashion closet, with the Telegraph Styling Team. The mission? To put together uplifting, flattering dresses-over-trousers combos that look pulled-together and soiree-ready (without inadvertently making me look like I’m pretending to be a member of All Saints in a throwback Smash Hits photo story).

First up, we try a print midi. I’m a tiny bit reluctant as I have gone off my (embarrassingly extensive) collection of mid-length frocks. They feel a little too safe and polite; not exciting enough for an evening on the town. Funnily enough, popping one over a pair of jeans (as I’ve done here) makes the whole thing feel cooler and younger.

Crepe de chine dress, £475, Really Wild; Slim jeans, £109, Le Jean; Velvet shoes, £160, Esska; Gold plated earrings, £195, Deborah Blyth 

In fact, it puts me in just the right mood to step out in a pair of velvet platforms. As style director Tona Stell points out, a button-through dress works particularly well, as you get to see a bit of leg (albeit denim-clad in this case); plus it’s easier to stride out without feeling too swaddled.

Next: a slip dress layered over a polo-neck or a tee is a timeless look that I love. In this instance, I’m wearing my own Simone Rocha slip from a couple of seasons ago (who is not in love with “a touch of red” this winter?). The flimsy silk fabric of this particular slip meant that layering over jeans looked a bit “lumpy and bumpy”, instead we tried these Samsoe Samsoe fluid pyjama-type pants which worked perfectly and were incredibly comfortable.

Dress is Sarah’s own; Wool jumper, £39.95, Muji; Viscose blend trousers, £150, Samsoe Samsoe; Patent shoes, £69, Charles & Keith; Pearl earrings, £165, Deborah Blyth 

There are some beautiful velvet slip dresses in the shops if you are looking for a heavier fabric. I liked the cosiness of the rollneck under the slip, but if I were to try this look again for a night out, I would go for a white linen t-shirt underneath instead, to make it feel a little less ‘encased’.

The third look was a revelation, a real party season game-changer for me. Let’s just say there’s a reason why Ghost dresses have been beloved by women for nearly 40 years. The winter white number which the team picked out is a beauty. The signature weighty viscose satin is incredibly flattering, skimming rather than hugging the body (this also makes it good for layering, not too clingy over belt loops and buttons).

Satin dress, £64.50, Ghost; Citizens of Humanity Straight leg jeans, £210, Harrods harrods.com; Platform shoes, £165, Esska; Pearl earrings, £165, Deborah Blyth 

As counter intuitive as it might seem, throwing this beautiful dress over jeans made it feel super wearable; less “bridesmaidy”, less “keep-for-best” than if I’d worn it with bare legs or tights. It’s got a little bit of that Kurt meets Courtney “Hollywood nightie and threadbare Levis” 90s allure. To quote Mr Cobain himself, it’s an outfit that says: “Come as you are.” It’s not too done, it feels relaxed and ready to party.

Oh, that’s another thing I love about the return of the dresses over trousers trend, you probably have all the components you need in your wardrobe already. I think we can all drink to that.