Helen Van Winkle, aka Baddie Winkle, found her way onto her 3.4M Instagram feeds and into a content business, after posting a photo of herself in a brightly colored Grateful Dead T-shirt and matching socks decorated with pink marijuana leaves. 

In an interview with CNN Money, the 93-year-old said her great-granddaughter “would come home from school every day, and she would say, ‘Gram, come look, you’re up 20,000 today.’ I mean, it just kept going.”

She became a fashionista. As she told Repeller, “I got to be an Instagram whatever-I-am. I did start wearing different clothes, younger clothes. And it was so much fun that I started wearing them all the time.”

.@BaddieWinkle, age 93, turned one #Instagram post and a fun, colorful, youthful sense of fashion into a #ContentBusiness. #ContentEntrepreneur #Stan Share on X

After gaining popularity online, she’s traveled for appearances at events in Los Angeles, Las Vegas, and New York and connected with other well-known fashion and lifestyle influencers. This year, she even made Insider’s list of 13 Inspiring Influencers Over 60 You Should Be Following. As of six years ago, Winkle was making up to $5K for every sponsored post for this Instagram content business. 

Why we’re a Stan: Helen didn’t let age get in the way of her expressing her style online. As she gained popularity, she doubled down on the fun fashion and turned into a content entrepreneur.

About the author

Shameyka McCalman is a wordsmith whose work often centers around fashion, art, and other creatives of color. She earned her communications degree from the University of Massachusetts Boston and enjoys sifting through clothes in local vintage shops, frequenting nearby plays, and gazing at exhibitions on view in museums.