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The 5 Style Icons Still Influencing What We Wear

Why these trailblazers continue to inspire fashion.

Kim Marcum

Published March 20, 2025

From sporty to sexy and back again, style icons of the past continue to influence what we wear and how we wear it. The presence of these five women can be felt today whenever we open our closets. We all can thank them for their fashion and style sensibilities that blazed trails we still follow.

Katharine Hepburn

Wearing her signature look of wide-legged pants, blazers and practical loafers, Katharine Hepburn was an anomaly in glamorous Hollywood of the early 1930s. But before long, her tailored, sportswear approach came to embody American style, according to Jean L. Druesedow, former director of the Kent State University Museum. The Ohio museum is home to nearly 1,000 of Hepburn’s costumes and offstage clothes.

At a young age, Hepburn determined that skirts were hopeless, recounts Druesedow in the video series, "Katherine Hepburn: Dressed for Stage and Screen." As Druesedow explains it, the four-time Oscar winner famously remarked, “Anytime I hear a man say he prefers a woman in a skirt, I say, ‘Try one, try a skirt'. ” Not surprisingly, the Kent State collection includes 30 pairs of Hepburn’s slacks, most in shades of beige and brown.

She also favored denim long before James Dean came along. “Kate was the first blue jeans woman. She wore blue jeans and it was unheard of,” recalled director George Stevens in the exhibit catalog, Katharine Hepburn: Rebel Chic. Stevens directed her in 1942’s Woman of the Year.

By 1985, Hepburn’s impact on American fashion was unmistakable, earning her a Lifetime Achievement Award from the Council of Fashion Designers of America. Today, the influence of her sporty style can be found in closets around the world.

Audrey Hepburn

With the opening shot of 1961’s Breakfast at Tiffany’s, Audrey Hepburn launched the little black dress into the fashion stratosphere and herself into the International Best Dressed List Hall of Fame. So popular it’s known by a mere three initials, the LBD has become the quintessential go-to garment for anything dressy. Its look and length have varied through the decades, but the little black dress remains the easy answer to the complicated question of “What should I wear to that?”

Onscreen and off, Hepburn often balanced the sleek simplicity of her evening wear choices with dazzling displays of glitz at her earlobes. Chandelier earrings often framed her face, complementing her short hairstyle or swept-back beehives. Those earrings — and that styling technique — are modern-day staples for projecting instant glamour.

But this Hepburn wasn’t only about playing dress up. She also left her mark on several casual trends, including two that are especially relevant to us. Just as she did with the little black dress, she turned the oversized white shirt into a women’s courtesy of Breakfast at Tiffany’s. An aspiring ballet dancer in her youth, she preferred ballet flats over towering stilettos that would have provided the petite actress with extra height. Her practicality is endorsed by women today as they embrace the ballet flats’ comeback for its comfort and sure-footed stability.

Jacqueline Kennedy Onassis

The past year has been filled with sleek, short tops that have come to be known as lady jackets. Often, they are in tweedy wovens, other times structured knits, all with statement-making buttons marching down their fronts. It’s hard to miss the muse for these buttoned-up jackets that capture the sophisticated essence of Jackie Kennedy's First Lady look.

During her White House years, the one-time intern at Vogue magazine also preferred the easy elegance of monochromatic dressing that’s so popular right now. But she didn’t shy away from a little drama here and there. On more than one occasion, she was spotted in a leopard-print coat, a pattern so prevalent today it’s very nearly a classic.

Once she married Greek shipping magnate Aristotle Onassis and morphed into Jackie O, oversized sunglasses became her calling card. As part of the resurgence of 1970s style, this size and shape is a standard offering in 2025. So too are the top-handle handbags she was fond of. Her signature shoulder bag remains a staple in the Gucci lineup as the Jackie 1961 and continues to inspire less-expensive knock-offs.

Marilyn Monroe

It’s hard to imagine Madonna or Kim Kardashian without the influence of Marilyn Monroe. She combined blonde and bombshell into one iconic label. The movie star’s glamour and sultry sexiness set the stage for the singer’s Blonde Ambition phase and the reality TV celebrity’s penchant for curve-clutching clothes. One could even argue there would be no SKIMS shape-shifting undergarments without Marilyn.

Besides body-conscious silhouettes, Monroe favored sparkle and shine, glitz and glamour. She was the original bedazzler — the first fairy godmother of rhinestones and crystals. Look no further than the much-ballyhooed gown she wore to sing “Happy Birthday” to President John F. Kennedy in 1962. Spangled with more than 6,000 hand-sewn crystals, the dress ignited a social media riot 60 years later when Kardashian wore it for a mere five minutes at the 2022 Met Gala.

While Hollywood stars can point to Monroe as their inspiration for red carpet dressing, the rest of us can thank her for popularizing several everyday styles. The skinny, knife pleats that have adorned dresses and skirts over the past few years are the stuff of movie magic in 1955’s The Seven Year Itch. That same white dress also brings us the halter neckline — a modern fan favorite for summer dresses and swimsuits alike. Speaking of swimsuits, the high-waist bikinis and ruched, one-piece maillots Marilyn sported are now mainstays at the beach for women of all ages.

Diane Keaton

In two star turns separated by several decades, Diane Keaton set fashion trends in motion that still reverberate. As the title character and sartorial inspiration of 1977’s Annie Hall, Keaton borrowed from the boys to make an international fashion statement defined by neckties, vests, bowlers and khaki dad pants. She went on to win an Oscar for the role, but it’s the costuming more than the story line that seems most memorable — and relevant.

Fast forward to 2003 and Something’s Gotta Give. This time Keaton wins a Golden Globe for a film with a much different wardrobe. Nestled into a swank beach house, she is decked out in sandy neutrals and luxurious fabrics. Like a fine wine, these elements must age. Finally, in 2022, the world was ready for the coastal grandmother look, making Keaton and her movie character its poster child. The aspirational vibe and monochromatic palette continue to hold sway today, evolving from classic beiges into more adventurous shades of burgundy (for winter) and buttery yellow (for spring) blended into a single outfit.

These five women were all fashion influencers before there was a name for their impact. Each left her mark by setting their sights on a personal Style North Star. Besides the fashion trails they blazed, we can find inspiration in their bold individuality and feel comfortable taking that path more often ourselves.

Which of the five women above do you admire most? Let us know in the comments below.

As a fashion editor in Dallas, Kim Marcum covered the international ready-to-wear collections in four fashion capitals and interviewed iconic designers from Giorgio Armani to Ralph Lauren. Later in her journalism career at the Orlando Sentinel, she was the senior editor on a Pulitzer Prize finalist in Local Reporting (2013) and on a project that earned the 2013 Diversity Award from the Freedom Forum/American Society of Newspaper Editors. In 2014, she joined Orlando Health, where she is the corporate director of strategic communications. She has two adult daughters and a grandpuppy.