The Chicest Over-40 Celebs Wear These 8 Items Nonstop

Who do you look to for outfit inspiration? While I certainly have my posse of millennial fashion influencers (hello, Pandora Sykes and Darja Barannik) as well as a handful of Gen-Z celebs (I’m looking at you, Kaia Gerber and Willow Smith) to excite my fashion choices, for the most part, it’s a strong and confident set of over-40 celebrities that most inspires my looks. What is it about these particular women that sets them apart? For one, there’s a confidence that exudes from their looks. They have the wisdom to know what does and doesn’t make them feel themselves, they don’t adhere to all the trends, and they’re able to pull off powerful statement pieces. Moreover, they all seem to anchor their outfits in quality staple pieces—from a timeless overcoat to seriously luxe leather boots. Ahead, see and shop the eight items the chicest over-40 celebs wear nonstop.

Long Wool Coat

J.Lo proves that a beautiful overcoat makes an outfit. While leather jackets and faux-fur coats have their time and place, it's the simple-yet-striking long wool overcoat that adds instant polish to any outfit. These over-40 celebrities wear them nonstop, and it's easy to see why.

Leather Knee-High Boots

Throughout fashion month, Anna Wintour was spotted in the most envy-inducing knee-high boots. From mock-croc styles like this one pictured to trending snakeskin, the fashion maven will always wear them tucked under a midi dress and coat for a seriously sophisticated look.

Tailored Pants

No one does relaxed tailoring quite like Victoria Beckham. Her wide-leg pants are a mainstay in her wardrobe—whether worn as a pantsuit, with a blouse, or simple white tee. Time to swap your jeans for some great-fitting trousers.

Midi Skirt

Sarah Jessica Parker has an array of fun and whimsical wardrobe delights, but it's a midi skirt (or dress) that she's rather partial to—along with many other celebs on this list. Try a pleated midi skirt with knee-high boots and sweater, and finish with a long overcoat.

Pointed-Toe Pumps

Smart, sleek, and polished, pointed-toe pumps are a staple in every over-40 woman's wardrobe. Michelle Obama wears them in neutral hues with practically every outfit, from pantsuits to dresses.

Little Black Dress

A little black dress defies age. Whether you're 20 or 40, it has the ability to solve any fashion dilemma. It's unquestionably flattering and always looks stylish. Kate Moss proves the power of an LBD no matter your age.

Skinny Jeans

Cindy, please tell us all your secrets! The one thing she will share is her love for skinny jeans. The 53-year-old has been seen donning them everywhere from L.A. dinners with her husband, Rande, to outings with her kids in New York. 


A classic blazer is a forever favorite in every over-40 woman's wardrobe. Jennifer Aniston is a big fan, throwing them over her signature jean-and-tee outfits and pairing them with dresses and sleek pants on the red carpet.

Blazers Over-40 Celebrities Love