Composite of Katharine Hepburn, Angelina Jolie and Janelle Monae
Composite of Katharine Hepburn, Angelina Jolie and Janelle Monae

11 of the most fashionable women in suits

From Katharine Hepburn to Janelle Monae, this is how you nail tailoring, says Prudence Wade.

Prudence Wade
Saturday 24 April 2021 07:30

Women wearing suits isn’t a new thing, but it still somehow has the power to shock. Call it a historical hangover: in the past, women have been expected to wear ‘feminine’ skirts and dresses, and crossing over into trousers was often seen as a threat to traditional masculinity.

Nowadays, it’s no quite so scandalous to see women in pants, but just think: it was only in 2013 that the 200-year-old French ban on women wearing trousers was overturned (although, of course, it hadn’t exactly been enforced).

Many a female style icon has had fun with androgynous fashion. These are some of our favourites…

1. Katharine Hepburn

Katharine Hepburn in 1951

Hepburn was a true fashion pioneer. From the 1930s and throughout her career she was a unique Hollywood star; instead of wearing gowns and smart dresses, she consistently wore tailored suits.

It was a brave choice for the time. Hepburn’s androgynous style was sporty and chic: her trousers tended to be loose, her blazers mannish and often worn with silk shirts and flat brogues.

2. Bianca Jagger

Mick and Bianca Jagger in 1970

The landscape of women’s suits changed drastically in 1966, when Yves Saint Laurent debuted Le Smoking: a tuxedo specifically designed for women’s bodies. Jagger famously wore a white version for her 1971 wedding to Mick Jagger and throughout the Seventies perfectly tailored, impossibly chic white suits became her signature look.

3. Diane Keaton

Keaton’s character in 1977 movie Annie Hall became an instant style star, with her loose tailoring and penchant for waistcoats and wide ties.

Keaton’s IRL style isn’t far removed from this – even now, she tends to wear strong tailoring and architectural silhouettes.

4. Grace Jones

For us, Jones is the undisputed champion of androgynous dressing. She knew how to make a strong suit seem simultaneously masculine and feminine – just take the artwork for her iconic 1981 album Nightclubbing, where Jones wears a boxy shouldered Armani men’s suit jacket with nothing underneath.

5. Annie Lennox

Annie Lennox at the 1999 Brit Awards

One of Eurythmics singer Lennox’s most memorable outfits was a Union Jack suit worn to the 1999 Brit Awards. It was bright, brash and had a bedazzled shirt underneath.

6. Hillary Clinton

Hillary Clinton in 2009

When Clinton joined Twitter in 2013, her bio read: ‘Pantsuit aficionado’. This pretty much tells you everything you need to know – Clinton’s spent her long career as a politician wearing pretty much the same type of pantsuit. The style rarely varies; the jacket tends to be buttoned to the top, occasionally she’ll add a silk shirt, and she prefers block colours.

7. Angelina Jolie

Angelina Jolie at the 2014 Baftas

Jolie gave a masterclass in chic tailoring at the 2014 Baftas, wearing a dramatic tux by Saint Laurent with a crisp white shirt, undone bowtie and killer heels.

8. Janelle Monae

Janelle Monae at the 2015 Brit Awards

In the early years of her career, Monae’s style was defined by a love of suits. You would rarely see her perform in anything less than a perfectly tailored two or three-piece, often styled with a wide brimmed hat. In 2015 Monae’s stylist Maeve Reilly told The Fader: “Janelle has always worn black and white as an ode to family members who wore uniforms for work; it wasn’t a style statement — though it’s become that.”

We particularly liked the patterned velvet suit Monae wore to the 2015 Brit Awards, finished off with a Prince-inspired ruffled shirt, a bright red lip and her signature hat.

9. Duchess of Sussex

The Duke and Duchess of Sussex in 2018

In one of her first public appearances after her engagement was announced, Meghan wore a black Alexander McQueen suit with Jimmy Choo stilettos, a Prada clutch and a white blouse. The look caused a stir – female royals are rarely seen in anything other than long gowns at formal events – but Meghan proved how stylish and appropriate a suit can be.

10. Zendaya

Zendaya’s fashion collaborations with Tommy Hilfiger have been all about Seventies retro styles. Patterned, flared suits were high on Zendaya’s agenda, and no one can wear them quite like her.

11. Cara Delevingne

Cara Delevingne at Princess Eugenie's wedding in 2018

There was a lot of fuss over Delevingne supposedly breaking the royal dress code by wearing a suit to Princess Eugenie’s 2018 wedding – but not only did the model clear her outfit with the bride-to-be beforehand, it was totally worth it. Leaning into the masculine side of tailoring, Delevingne wore cigarette trousers, a jacket with tails and a top hat by Armani, showing how women can – and should – wear suits to weddings.