Fashion Street Style Older "It" Girls Who Prove Style Gets Better With Age By InStyle Editors InStyle Editors Facebook Instagram Twitter Our editors and writers comprise decades of expertise across the beauty, fashion, lifestyle and wellness spaces in print and digital. We prioritize journalistic integrity, factual accuracy, and also having fun with every story we share. InStyle's editorial guidelines Published on April 14, 2015 @ 12:05PM Pin Share Tweet Email Trending Videos Photo: Getty Images North America Flip through some of our favorite stylish and wildly successful leading ladies. 01 of 27 Jane Birkin WireImage The singer, actress, and model has always erred on the side of cool. So much so that her last name is widely known for its attachment to Hermes' signature structured handbags. 02 of 27 Diane Sawyer Michael Loccisano/NBC/NBCU Photo Bank via Getty Images Leave it to Diane Sawyer to ask the probing questions. The famed news journalist always keeps calm even when faced with the toughest interview subjects. 03 of 27 Iris Apfel FilmMagic This New York resident is known for her love of color and large, statement-making baubles. She's so loved that a new documentary, Iris, was filmed in honor of her style and fashion legacy. 04 of 27 Dame Maggie Smith Landov Though she's most recently known for her role as Dowager Countess of Grantham in PBS' Downton Abbey, actress Dame Maggie Smith has delivered unforgettable performances for decades. 05 of 27 Vivienne Westwood WireImage British designer Vivienne Westwood has continuously pushed the fashion boundaries for decades. She's respected for the punk-defining garments she created in the '70s. 06 of 27 Betsey Johnson D Dipasupil/FilmMagic The energy-filled designer is not one to shy away from summersaulting her way across her pink-splattered runway. Long live Betsey! 07 of 27 Cher FilmMagic No matter how hard we try, Cher will always stay on our minds. The songstress, actress, and Oscar winner is undoubtedly an icon. 08 of 27 Norma Kamali Getty Images North America The American designer built her career on dressing fashionable women and being at the forefront of technology. 09 of 27 Carolina Herrera Steve Granitz/WireImage The crisp white shirt. The large, billowy floral midi skirt. The signature blonde hair. Ms. Herrera's designs are instantly recognizable thanks to their over-the-top glamour and ability to make women gleam. 10 of 27 Jane Fonda Getty Images North America Very few people can still rock Balmain at age 77. 11 of 27 Helen Mirren Andrew H. Walker/Getty Images Her striking gray locks are reason enough to love her. 12 of 27 Joni Mitchell Steve Granitz/WireImage Though no longer with us, her music, art, and peacful legacy will always live. 13 of 27 Dame Judi Dench Frederick M. Brown/Getty Images The Oscar-winning actress is as stunning as she is talented, known for playing well developed, complex, characters throughout her career. 14 of 27 Charlotte Rampling Getty Images Europe The English actress has successfully managed to age gracefully and show off her alluring beauty. 15 of 27 Catherine Deneuve Larry Busacca/Getty Images Perhaps it's her Parisien background, but Catherine Deneuve is a revered beauty famously recognized for playing charming and gregarious characters in French films. 16 of 27 Twiggy Pascal Le Segretain/Getty Images It's impossible not to be "mod" for Twiggy. The model came to fame in the '60s for her signature short hair and cute, gleaming smile. 17 of 27 Debbie Harry Getty Images Europe Debbie Harry never stops being daring. The singer is most recognizable as the lead singer of punk band Blondie. 18 of 27 Queen Elizabeth II Samir Hussein/WireImage What's not to love about a woman who's simply The Queen. 19 of 27 Sophia Loren Axelle/Bauer-Griffin/FilmMagic Bodacious brunette Sophia Loren remains a classic beauty. 20 of 27 Jessica Lange WireImage Simply perfection. The American Horror Story star is known for her beauty. She most recently fronted Marc Jacobs' beauty campaigns. 21 of 27 Meryl Streep Getty feed for People The actress is constantly revered at awards shows year after year. She's a striking beauty, whether playing a vicious editrix or an evolving cook. 22 of 27 Julie Andrews WireImage Who doesn't have memories of watching The Sound of Music as a kid? The award-winning actress will forever hold a special place in our hearts. 23 of 27 Vera Wang FilmMagic Once a magazine assistant, designer Vera Wang is popular not just for her namesake ready-to-wear collections, but for her famed white bridal gowns. 24 of 27 Patricia Field Michael Stewart/Getty Images Stylist and entrepreneur Patricia Field is most famous for her spot-on costume design on television hits like Sex and the City. 25 of 27 Aretha Franklin FilmMagic When it comes to Aretha Franklin, the singer deserves all the r-e-s-p-e-c-t imaginable. She commanded the sound of the '60s and continues to do so today. 26 of 27 Diana Ross Dominique Charriau/WireImage Big hair. Big voice. Huge legacy. 27 of 27 Diane von Furstenberg Getty Images North America American designer Diane von Furstenberg, otherwise known as DVF, celebrates the empowerment of women. The creation of her now famous wrap dress in the '70s was groundbreaking in fashion.