Chic Women Over 50 Are Wearing Cuffed Jeans With Chelsea Boots

A few weeks ago, the moment the clocks turned from 2025 to 2026, everyone suddenly became obsessed with stovepipe jeans. There was a good reason for that. Tailored and sophisticated, denim is the perfect choice if you want to look more elegant in the new year. That being said, it’s not only It’s an option for jeans lovers, a point proven by over-50 celebrities known for their timeless and understated sense of style. There’s already been a movement between Sandra Bullock and Kate Winslet to ditch stovepipe denim and put cuffed jeans at the top of fashion.

Bullock was spotted out and about in Los Angeles earlier this week, and as always, she wore an effortlessly cool ensemble that’s perfect for the cool weather currently blanketing the country (I mean, when you consider mid-60s to be cool, whereas today in New York it felt like -1 degree). Specifically, the actress opted for a black chunky turtleneck sweater and light wash jeans with cuffs. From there, she added lug-sole Chelsea boots, also in black, and a larger version of The Row’s N/S Park Tote. There were no added embellishments or statements. Instead, her outfit was classic and chic, just like all denim outfits. should Get used to it.

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

Despite having one of fashion’s most beloved totes slung over her shoulder, the best part of Bullock’s outfit, in my opinion, was her hemlined jeans and Chelsea combination. boots. The slightly cropped hem of her denim perfectly showed off the most famous part of this style: the shaft of her boots. These boots don’t have a heel, but have a thick lug sole, perfect for running errands. Also, if you’re like me, you won’t be enjoying the sunshine this January, but instead, it’s perfect for snowy weather. blizzard.

My theory that cuffed jeans and Chelsea boots are the perfect denim combination was first confirmed when I came across a photo of Winslet heading to a movie shoot. The Late Show with Stephen Colbert Late last year, she wore her own version of the foolproof outfit. of titanic The actress wore a cream sweater and faded dark wash cuffed jeans, which she accessorized with her trusty brown Red Wing Chelsea boots and a matching oversized shoulder bag. Just like Bullock, Winslet’s outfit also looked put together in a way that only someone who truly understands their personal style can. result? It’s a chic, hassle-free combination that works every time.

About Kate Winslet: red wing boots

Sure, stovepipe jeans are worth the investment, but so is another denim trend for 2026. If you’re going for cuffed jeans this year, we recommend styling them with Chelsea boots. Keep scrolling to shop both pieces of this hassle-free outfit.

buy cuffed jeans

buy chelsea boots