The Annie Hall-Esque Trouser Trend Uniting Julia Roberts and Kate Moss

Amidst the flurry of Hollywood stylist Elizabeth Stewart’s Instagram posts about Jessica Chastain’s Gucci princess dress and Rebel Wilson’s twinkling Moschino transformation at the Oscars, there was one celebrity look that really stood out. It was of Julia Roberts. She was not on the red carpet, but mid-fitting, and smiling—presumably about the excellent Michael Kors trousers now in her life.

The smart high-waisted, wide-leg trousers echo the trend for tailored pants that is now reaching its apex. The Row is to thank. Mary-Kate and Ashley Olsen have been majoring in versatile luxury basics since they set up shop, but it was only once the twins tempted the supermodels out of their Alo Yoga leggings and into their Igor pants that everyone else considered smartening up.

The brilliant thing about the pleated-at-the-top, louche-on-the-bottom trouser style is that although they give off a refined air, they are surprisingly easy to wear. Tuck a white tank in (another of this season’s cult buys), and throw a breezy shirt over the top and you’re giving shades of Kendall Jenner and Rosie Huntington-Whiteley. Do a crop top and trainers and you’re leaning into Jennifer Lawrence and Hailey Bieber territory. Grandaddy knits more your thing? Add a silk neck scarf and emulate Alexa Chung.

Photo: Getty Images

Photo: @rosiehw

There are no strict style rules for these wide strides apart from the length. These are floor-skimming trousers that look ultra-relaxed with a Birkenstock or trainer, or can be elevated (literally) with a heeled sandal (happily, you can buy these at The Row, too—if you have the budget).

The Row Igor pleated cotton-panama wide-leg trousers

The Frankie Shop Bea pleated fresco trousers

If switching from slim-cut jeans to baggy denim was a big leap of faith for you, then admittedly the mannish pant trend might seem foreign. The great thing is that there’s a whole archive of tailored trouser enthusiasts to consult before buckling up (a belt is essential for maximum big pant success). It’s likely Stewart referenced original “menswear” enthusiast Diane Keaton when proposing the new look to Roberts. The name Annie Hall cropped up during the autumn/winter 2022 shows thanks to Louis Vuitton’s breezy work pants worn with billowing shirts and floral ties. So too, Amelia Earhart and Katharine Hepburn.

Photo: Getty Images

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