Chic Women Over 50 Are Wearing Cuffed Jeans With Chelsea Boots

The second our clocks turned from 2025 to 2026, a few weeks back, everyone suddenly became obsessed with stovepipe jeans, and for good reason. They’re tailored and refined—a perfect denim choice if you’re going for a more elegant look in the new year. That being said, it’s not the only option for jeans lovers, a point proven by several over-50 celebrities who are known for their timeless, understated sense of style. Between Sandra Bullock and Kate Winslet, a movement is already stirring to dethrone stovepipe denim and let cuffed jeans take its place on fashion’s top step.

Bullock was spotted earlier this week while out and about in Los Angeles, and as usual, she wore an effortlessly cool ensemble that was perfect for the cooler weather sweeping the country right now (that is, if you consider mid-60º temperatures cool—meanwhile, it felt like -1º in NYC today.) Specifically, the actress chose a black, chunky turtleneck sweater with cuffed light-wash jeans. From there, she added lug-soled Chelsea boots, also in black, as well as a large version of The Row’s N/S Park Tote. There were no frills or statement additions. Instead, her outfit was classic and chic, which is exactly how all denim outfits should be.