Women Over 50 Aren't Wearing Sneakers With Dresses—They're Wearing Them With This and This

How to look as cool as Naomi Watts, no matter your age.

By Swedan MargenSeptember 20, 2026

Women Over 50 Aren't Wearing Sneakers With Dresses—They're Wearing Them With This and This

Sneakers are a wardrobe staple no matter what stage of life you’re in. Even the type of sneakers women wear during any given season is often the same. What can differ is how women of different age groups style them. While women in their 20s love wearing sneakers with dresses and skirts, I often spot women age 50 and up wearing them with two other popular items: leather bomber jackets and relaxed jeans. And Naomi Watts is just the latest example.

While arriving in Spain for the San Sebastian International Film Festival last week, Watts was photographed wearing a black leather bomber jacket slung over one shoulder, relaxed-fitting bootcut jeans, and Adidas Samba sneakers, completed with a light blue sweater, silk Hermès scarf, and a slouchy Chanel flap bag. As you'll see, it's an elegant, low-key way to style sneakers that would work no matter what age group you fall into (and what type of sneakers you prefer). Keep scrolling to see the chic outfit on Watts for yourself and shop the three key pieces (sneakers included, of course.