I’ve dressed like a tomboy since I was a teenager: think unisex shirts, brogues and tailored jackets. Now I’m 50, all that’s changed is the name – I call it Gentlewoman Style

Most of the women whose style I admire dress a bit like men. I’m thinking marvellous Maxine Peake (and not just when she’s playing Hamlet), American Vogue’s preppy fashion director Tonne Goodman and, a particular favourite, the French model and muse Inès de la Fressange. These are elegant tomboys; women who opt for flat shoes over frou-frou, who would rather shop at Margaret Howell than Manolo Blahnik.

Of course, this is more than just a look, it’s a mindset – it’s about dressing to please yourself. By transforming menswear into outfits to suit to her active, independent lifestyle, Coco Chanel blurred the boundaries, dismissed rigid dress codes and, as the legendary American Vogue editor Diana Vreeland once said, “invented the 20th century for women”.



At 15, I didn’t mind being called a tomboy, but now that I’m 50, I’ve decided it’s time to reclassify. In my new book out next year, Style Forever: the grownup guide to looking fabulous, I call this Gentlewoman Style. The older I get, the more I appreciate this androgynous approach, where everything is carefully considered but nothing looks too “done”. Being gentlewomanly is the perfect midlife style solution: the figure-flattering jacket, the essential black trousers, the go-everywhere mannish brogues, all of which are effortlessly chic and infinitely real. And this is why I think Julia Roberts looks better in the Givenchy spring/summer 2015 ad campaign than she’s ever done on the red carpet.

The dandyish coat

Classic menswear styles in eye-catching colours are an excellent way to get the androgynous vibe. If money’s no object, opt for Paul Smith. For a more purse-friendly version, try M&S – last year’s standout pink coat is available in 10 different colours this season.

The boy-meets-girl shirt

From Patti Smith on the cover of Horses to Sofia Coppola at Cannes, the oversized shirt never goes out of style. My favourites are from Margaret Howell’s MHL line – men’s or women’s, I have both: the quality of the cotton is superb, they last and last, and wash like a dream.

The tailored jacket

Tailoring is an easy way to smarten up and sculpt the figure. Newish label Atea Oceanie is aimed at “boyish, feminine women who are comfortable in their skin and effortless in their style”. The double-breasted Hepburn blazer is inspired by menswear and named after the paradigm of a gentlewoman, Katharine.

The essential black trousers

Sounds boring, but a pair of well-fitting black trousers can make any woman look like a Hollywood siren. When paired with an oversized shirt or boyfriend jacket, I prefer to keep proportions in check by opting for a slim cigarette style, such as Acne’s Skin Black jeans or Eileen Fisher’s waxed skinny jeans.

The go-everywhere, mannish shoe

It is worth spending money on a decent pair of shoes. Northampton is the home of quality British footwear: Grenson, Joseph Cheaney & Sons, and some styles by Church’s, Toast and M&S Best of British are manufactured in the “shoemaking capital”. Brogues, lace-ups and monk shoes all look good with slim and wide-legged trousers, or team metallic styles – such as Grenson’s G:Two Collection Rose – with a maxi skirt.

The twist

This final flourish is what helps put the woman into Gentlewoman Style. Pin a cluster of diamanté brooches to a lapel, add a beautiful silk neck scarf and a narrow leather belt to a mannish jacket, or try a pair of chandelier earrings and metallic shoes. And, as US journalist and blogger Lizzie Garrett Mettler confirms in her book Tomboy Style, “The complete look requires the right woman underneath.”

Alyson Walsh blogs at That’s Not My Age, @thatsntmyage

This article contains affiliate links, which means we may earn a small commission if a reader clicks through and makes a purchase. All our journalism is independent and is in no way influenced by any advertiser or commercial initiative. By clicking on an affiliate link, you accept that third-party cookies will be set. More information.