In an age of homogeneous stars, all botoxed and skinny in their tight jeans and Ugg boots, it is good to revisit the more unconventional stars of Hollywood’s Golden Age, who sought to break the mould. They are the women who dared to wear trousers when it was frowned upon and who made them look glamorous. Nell Darby takes a closer look.

Katharine Hepburn (left) was tall and lanky and so suited wearing trousers. She would dress in men’s suits or trousers when women were expected to dress more femininely. It is testament to her popularity that when women saw Kate wearing men’s clothes, they started doing so themselves.

Hepburn herself said that she wore trousers because they were more comfortable, although she also liked a more masculine look, wearing trousers with brogues and mannish shirts. She was also pictured pairing her loose-legged trousers with ultra-feminine wedge heeled shoes and immaculate make-up.

This isn’t to say that Hepburn was the only woman in the Thirties wearing trousers. Oxford bags, wide-legged trousers that originated at Oxford University, had been around since the Roaring Twenties, and at least two other Hollywood stars were seen in them.


Marlene Dietrich was one of them. She famously declared, “I dress for myself. Not for the image, not for the public, not for the fashion, not for men.” She was a habitual wearer of loose trousers, and managed to look effortlessly striking. One of her favourite looks was a trouser suit, short, fitted single-breasted jacket with tailored yet loose trousers. To accessorise, she would wear a polo necked jumper underneath, and a beret (at a jaunty angle, of course).


Greta Garbo (above) mastered the androgynous look around the same time, startling a conservative society by wearing trousers in everyday life. She teamed them with flat shoes, including ballet-style pumps, like Hepburn, she was a tall woman and didn’t feel the need to always wear heels.

A later picture of her by Cecil Beaton shows her in natty neck scarf, black fitted shirt, loose culottes,still with a nipped in waist, and calf-length boots. The culottes and boots combination sound wrong, but look strangely good.

These stars preempted the trend, during the Second World War, for women to borrow their husbands’ trousers to go to work in. More and more women realised their practicality, and the wearing of trousers by women had become widespread by the end of the war.

Despite the obvious comfort of a pair of baggy trousers, a lesson can be learned from these Hollywood stars in how to wear them yet maintain a chic elegance. Wear the trousers with a clean, white, fitted shirt and a polished pair of flat shoes, and you can look as effortlessly chic as Hepburn and co.

2 Responses

  1. Camilla Stacey


    I’m Camilla from the Samuel Windsor blog team. We’re producing ‘A Gentleman’s guide to wearing Womenswear’ at the moment, and would like to use a quote from this story.

    We will of course credit and link to you.

    I hope that’s ok – if you have any questions please just drop me a line.

    I’ll be sure to let you know when the article’s published.

    Kind regards,


    Samuel Windsor blog team

  2. Camilla Stacey


    I just wanted to let you know that the “The Gentleman’s guide to wearing Womenswear” article I mentioned recently is now live on the Samuel Windsor blog at:

    Thank you so much for the use of your quote – it’s much appreciated.

    I hope you like the article – please feel free to share it with your networks; there may be something of interest for them there. If you like to use Twitter, there’s a handy tweet link at If you’re more of a Facebook fan, try this link:

    Thanks again

    All the best