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.

(Image credit: Backgrid)

On Sandra Bullock: The Row Large N/S Park Tote Bag ($3250)

Even with one of fashion’s most beloved totes on her shoulder, the best part about Bullock’s outfit, in my opinion, was the combination of her cuffed jeans and Chelsea boots. The slightly cropped hem of her denim perfectly showed off the shaft of her boots, a.k.a. the part the style is most famous for. The boots didn’t have a heel, but a thicker lug sole, making them great for running errands, or even snowy weather, if you, like me, aren’t enjoying sunshine this January, but instead, a blizzard.

My theory that cuffed jeans and Chelsea boots are the perfect denim combo was only backed up when I found photos of Winslet heading into a filming of The Late Show with Stephen Colbert at the very end of last year and wearing her own version of the foolproof outfit formula. The Titanic actress donned a cream-colored sweater with faded, dark-wash cuffed jeans, which she paired with her trusty brown Red Wing Chelsea boots and a matching oversized shoulder bag. Like Bullock, Winslet’s outfit appeared to be thrown together in a way only someone who truly understands their own personal style can do. The result? A chic, no-fuss combination that works every time.

Kate Winslet flashed a warm wave as she headed into The Late Show with Stephen Colbert, sporting a cozy cream sweater, cuffed jeans, and worn-in brown Chelsea boots.

(Image credit: Backgrid)

On Kate Winslet: Red Wing boots

So, while yes, stovepipe jeans are more than worth investing in, so is another 2026 denim trend, and if you want to do cuffed jeans right this year, styling them with Chelsea boots is the way to go. Keep scrolling to shop both pieces of this low-effort outfit.