The inscrutable Katharine Hepburn is remembered by many for so many different things. She was an actress, pin-up model, a rebel, politically aware, progressive, a fashion icon, and more. One thing that can definitely be said of Katharine Hepburn is that she was ahead of her time.

She was an independent woman before it was socially acceptable to be an independent woman, particularly in Hollywood. She was glamorous but was more at home in jeans and a turtleneck. She was ivy-league educated but chose to work in the movies. In short, Katharine Hepburn was her own woman, who walked to the beat of her own drum and not the beat of what was socially dictated.

A young starlet.

Katherine Hepburn - Vintage Style Modern Tips

Early Life and Movies

The gorgeous and talented Katharine Hepburn was born into an upper-middle-class, liberal, educated family in the state of Connecticut. She went to Bryn Mawr College, a liberal women’s college outside of Philadelphia, and majored in history and philosophy. It was at Bryn Mawr that she was bit with the acting bug and it was there that she decided to pursue a career in acting.

Edith Head dressed her in many movies.

She worked on the stage for a few years and was discovered by Hollywood in 1932. It was bound to happen with her beauty, distinctive voice and presence. Some of her most well-known films were: Stage Door, Bringing Up Baby, The Philadelphia Story and The African Queen. She continued to work until late in her life, most notably on the films Lion in the Winter and On Golden Pond. She passed away at the age of 96 in 2003.


Fashion Icon

Hepburn did not set out to be a fashion icon. In fact, she was not much of a fan of all the trappings of Hollywood. She actually eschewed the formality and the discomfort of women’s clothing at the time especially skirts. She has been called many things in regard to her fashion impact (both anti-fashion and androgynous, among others) but she really never intended to be a fashion trendsetter she just wanted to be comfortable. In summary, it wasn’t that she set out to create her own style, she was only being herself!

This notion totally went against the social norms of the time when women were expected to be decked out and dazzling all the time, especially a glamorous Hollywood star. Women were expected to bend to the social and fashion mores of the time, no matter how uncomfortable and Hepburn just didn’t play along with that mentality at all.


For example, she was one of the few daring individuals who wore trousers before it was socially acceptable to do so. Always one who was ready with a great quotable statement, this is what she said about skirts:

“I realised long ago that skirts are hopeless,” she once said. “Anytime I hear a man say he prefers a woman in a skirt, I say: ‘Try one. Try a skirt.’ “

Hepburn received a lifetime achievement award from the Council of Fashion Designers of America in recognition of the influence she played on the fashion world.


Katharine Hepburn is well remembered for her popularisation of trousers for women. Partly, it was due to her vim and vigour attitude, but she also looked smashing in a pair of trousers. She had a gorgeous figure for the long legs, small waist and a graceful way that she carried herself. She looked powerful in trousers in the same way that some women look powerful in a pencil skirt and heels.

As for why she took to wearing trousers Hepburn said:

“I like to move fast, and wearing high heels was tough, and low heels with a skirt is unattractive. So pants [trousers] took over.”

Katherine Hepburn - Vintage Style Modern Tips



Hepburn, while a casual dresser at heart, understood how Hollywood worked and she could also glam it up on the red carpet and silver screen alongside her contemporaries. She wasn’t one to be outdone either and – possibly from her athletic streak – was somewhat competitive. She is also known to have said that she didn’t care a bit about acting  – she just wanted to be famous and she got it that glamour was part of the game.

Katherine Hepburn - Vintage Style Modern Tips

How to Get the Katharine Hepburn Look Today?

So much of Katharine Hepburn’s style had less to do with what she wore than how she wore it, so it is a bit difficult to come up with a guide on how to replicate her look exactly.

Here are a few tips though.

You Must Invest In Menswear-Inspired Pieces

  • One word. Menswear. You must invest in menswear-inspired pieces. This autumn that is fairly easy to do since many designers have been inspired by this trend.
  • When you do wear skirts and dresses, try very tailored styles or styles that have tailored elements.
  • Go long and lean. Hepburn was the queen of creating a gorgeous, long, lean line for herself.
  • SGo with soft hairstyles. Hepburn preferred her clothing to be functional and hard-edged, but she always wore her hair curled, piled atop her head or in other soft and feminine styles.
  • As far as makeup, Hepburn always had a strong brow and a strong lip.
  • Wear oxfords and penny loafers.
  • Wear trousers with cuffs.
  • Roll up your slouchy jeans and wear them with loafers and an oversized button-down shirt.

Additionally, it’s always good to have a bit of attitude and confidence.

So work on that I don’t give a damn approach that Kate had.

Katherine Hepburn - Vintage Style Modern Tips

Casual Update Look

Here’s an example of how to put it all together for an updated Katharine Hepburn casual look. It’s reminiscent of Hepburn without being too literal.

  • Carlton Blouse
  • Asawa Snakeskin Brocade Trousers
  • Tignanello Handbag, Vintage Classics Leather Shopper
  • Stingrei Booties

And here’s an updated modern pure glamour Hepburn look. Here’s wishing for an occasion to wear this!

  • Two Row Memory Chain Necklace
  • Sly Boxy Clutch
  • Lanvin Strapless Duchesse Satin Gown
  • Gold Glitter Platform Court Shoes