6 Jennifer Aniston Outfits That Look Just as Cool 25 Years Later

Jennifer Aniston tends to avoid trends, sticking to timeless basics—she has been wearing blazers and straight-leg jeans for decades. As she avoids gimmicky outfits, you can re-create any of her looks from any decade and still look relevant. We had a deep dive through her '90s style and found six looks that look just as cool 25 years later. There are the throw-on-and-go going-out outfit and the floral dress and-trainer combo that you'd spot every single weekend in Victoria Park. Keep scrolling to see—and shop—Jen's '90s style.
Style Notes: Jen wore a floral strappy maxi dress over a white tank top with a pair of white pumps. She is also wearing the 2018 key accessory—a pair of micro sunglasses.
Style Notes: High-waisted jeans and a silky shirt couldn't be simpler, but it still looks timeless.
Related: Winter 2018 Fashion Trends: The Only Looks You Need to Know
Style Notes: This black strappy slip dress and these stilettos make an impact whatever the decade.
Style Notes: If you take a look at Jen's feet, you'll notice she's wearing the strappy sandals you'll see all over Zara.
Style Notes: This outfit, featuring a blazer, straight-leg jeans and a pair of pointed boots, could be our autumn uniform come September.
Style Notes: Note her rope bag that looks like something from new cult brand Alienina.
Shop the Look
Related: Gwyneth Paltrow's '90s Wardrobe Couldn't Be More 2018
Next up, see this summer's It dresses that are still in stock.
Opening Image: Getty Images

Emma is a freelance fashion editor with over 15 years experience in industry, having worked at The Telegraph, Grazia and, most recently, British Vogue. Emma was part of the founding team of Who What Wear UK, where she worked for six years as Deputy Editor and then Editor—helping shape the team into what it is today is one of the biggest privileges of her career and she will always see herself as aBest Knockoff Luxury Clothing girl, contributing to both the US and UK sites. Whether she's writing about runway trends or spotlighting emerging brands, she aims to write about fashion in a way that is democratic and doesn't promote over consumption.
-
I Thought I Hated '00s Fashion, But These Throwback Sandal Trends Are Actually Chic
Serving Y2K realness.
-
This Is the Only Way to Wear Your Baggy Jeans This Summer, According to Stylish Celebs
I know you pay attention to fashion if you're wearing this style...
-
Suddenly, Jennifer Lopez's Favourite Summer Shoe Trends from the '90s Are Back
I'd legitimately wear them all tomorrow.
-
Jennifer Aniston Just Wore the Casual Shoe and Jeans Combination That Works in London and L.A.
Take note.
-
Suddenly, Jennifer Aniston's Favourite Sandal Trends from the '90s Are Back
An icon's go-tos.
-
Jennifer Aniston and French Women Have Always Been Loyal to These Suddenly Trending Jeans
And for very good reason.
-
14 Rachel Green Outfits We'd Happily Wear in 2025
Friends' resident fashion girl is still our style inspiration.
-
Sorry, But the '90s Did Leopard Print Better—6 Looks Inspiring My 2024 Wardrobe
The best era.