Love it or loathe it, it seems Y2K fashion is here to stay. Moving on from crop tops and cargo pants, we’re now firmly back in the dresses-over-trousers era, which, to be honest, we aren’t too upset about. However, to successfully pull off a new(ish) trend, you need a bit of confidence and the knowledge that you’re doing it right, so we caught up with stylist Sarah Barlow and Stylist’s own fashion director, Lucy Reber, to find out how to style the resurgent trend this time around.

“Styling dresses over jeans is such a vibe; it takes me back to being 14 quicker than anything else,” says Reber. “I like to think I’ve amassed a few tips on how to do it in the intervening years.” 

It may have seemed like a slightly strange trend a decade or so ago, one that touched on the high/low styling rule (where a formal fashion item is pared back with a more casual pick). But the dress-over-trousers look seems to have taken on a much more elevated approach this time around. 

“I love the idea of wearing jeans with something with dramatic hems and a wide trapeze shape – think Cecile Bahnsen or Simone Rocha,” says Reber, stressing the importance of having fun with shape and texture. “To balance out your silhouette, you could also opt for a lighter silk option, again with puffed sleeves – maybe something cool in silk or sequins.” 

If you’re a regular reader, you’ll probably know how much we love a dress, so be sure to take a look at our shopping pages for gingham, poplin-sleeve and bubble-hem dress inspiration.

For stylist Sarah Barlow, the key to nailing this look is contrasts. “Denim itself is quite a rigid and masculine texture, so offset it with a feminine, ethereal dress on top with lots of movement, such as a light floaty slip, perhaps in a neutral or pastel shade,” she says. This corresponds with what fashion insiders have opted for, as seen in the London and Copenhagen Fashion Week street style snaps we’ve included for inspiration.

When choosing jeans, Reber offers a few key pointers. After all, skinny styles are still sitting at the back of our wardrobes, waiting for the day when they become cool again. “I only really want to see a dress over something washed-out, wide-legged and worn low and loose,” Reber says. So white, grey and light-wash options are all key contenders, alongside a darker, inky denim if you’re looking for a more daring design.

As well as looking stylish, a key point of the trend is that it helps to extend the lifespan of our wardrobes. “Layering these typically summery dresses over jeans is an easy way of making them work in the colder months,” says Barlow. And experimenting with new ways to wear our favourite fashion finds, no matter the weather, is certainly a cause we can get behind. 

So next time you’re looking to make a slight style statement, get hold of your jeans and your favourite evening dress and try to combine the two. You may find it gives the best of both worlds: comfy and chic. 

Images: Getty; courtesy of brands