When you hit a certain age, it’s easy to idealize your younger self—those days when you didn’t have to think about worry lines, grey hairs, or even age spots when dressing yourself. But everyone knows that the real key to looking good is confidence, and as you get to know yourself with age, cultivating a strong sense of style should be easier than ever. If you don’t believe us, just take a look at these five fashionable women: they’re all well over 50-years-old, and dress in everything from big jewelry and punchy prints to classic white blouses and blazers, proving there’s no one way to look good over 50. One major thing these women all have in common? None of them are concerned with “dressing their age.”
No list of fashionable older women would be complete without Iris Apfel. This “it girl” is now in her 90s, but she continues to experiment with the bold patterns, chunky jewelry, and oversized glasses that have come to define her style. When you learn a bit about Apfel’s past—an art history major who worked as an interior designer and later launched a textile firm with her late husband—it’s not hard to see why she’s often described as a “rare bird of fashion.” But it’s not just her unique look that’s so inspiring—it’s the unapologetic attitude she has to go with it. In her own words: “Dress to please yourself. Listen to your inner muse and take a chance.”
Although Anna Wintour has been quoted saying that she doesn’t see herself as an “icon,” the fashion world would beg to differ. Now in her mid-60s, Wintour has been at the helm of American Vogue since 1988, so it should come as no surprise that she knows how to dress. Beyond her signature bob and sunglasses, Wintour is known for wearing well-tailored pieces with cinched-in waists and conservative necklines, topped with statement necklaces. Her style has been described as “consistent,” but it’s her ability to pair bright prints and rich textures with her petite body type and aloof personality that’s really impressive.
This Venezuelan-American fashion designer has dressed countless public figures, including First Ladies Michelle Obama and Jackie O. But she’s known for her exceptional style when it comes to dressing herself as much as others. Often seen wearing a simple white blouse and jewels—whether it’s a flashy necklace, dangling earrings, or a chunky bracelet—Herrera’s personal style can be described as effortless elegance. Though much like her collection, she often mixes these refined staples with bright or printed skirts that add a touch of sass.
Still known for her supermodel stardom, Iman was the first African to grace the cover of Vogue in 1979, which helped catapult her into the spotlight and break down racial barriers for models of colour in the process. Now a fashion and beauty mogul in her 60s, she’s as flawless as ever—and we’re not just referring to her giraffe-like legs and supple-looking skin. They help, of course, but they’re not the only reason she looks about half her age. It also has something to do with the fact that she always knows exactly what to wear. Unlike some of the other ladies on this list, she doesn’t really have a “signature look.” Instead, she does her best to play up her strongest features, whether that means wearing a structured pant suit with flared legs or a safari jacket paired with piles of enamel and wood bracelets.
As the fashion director at British Vogue, Lucina Chambers has built a reputation as one of the world’s best stylists. Admired for the eclectic vision she brings to every shoot, her personal style is very much her own. In fact, the way she pairs clothing—layering stripes and patterns of every colour in a way that almost never matches—has been described as “impossible to copy.” She’s less tidy-looking than other fashion icons her age, but she dresses in a way that feels comfortable to her. The real takeaway with Chambers’ style, like Apfel’s, is to never let others dictate your style.
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