Simplicity is the name of the game when it comes to Jennifer Aniston's style. She's been wearing sleek, fuss-free outfits for decades, and her looks have definitely stood the test of time. Her style is so timeless, in fact, that we bet you can't correctly guess what year each of these photos was taken.
Her early-2000s outfits would look right at home in 2018 while her present-day ensembles could have easily been from any year. Scroll down to see how her style has evolved over the years and tackle our challenge. Warning: Answers are written directly under the photo.
Answer: 2005
Answer: 2003
Answer: 2009
Answer: 2004
Answer: 2009
Answer: 2017
Answer: 2009
Answer: 2018
Shop Our Jennifer Aniston Capsule Collection
1. LBD
Available in sizes UK 6 to UK 14.
2. Strappy Sandals
3. Black Tank Top
Available in sizes XXS to XXL.
4. Denim Shorts
Available in sizes 23 to 32.
5. Flip Flops
6. Slip Dress
Available in sizes XS to L.
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I'm Channeling '90s Jennifer Aniston and Halle Berry With These 10 Fall-Ready Looks From NordstromMinimalism at its finest.
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Basic Jeans Aren't Out, But This Denim Trend Feels Way More 2025It's not white, dark wash, or chocolate brown.
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This Is the Least-Scary Way to Wear the Sheer Clothing TrendJ.Law approved.
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Jennifer Aniston Traveled in the Denim Trend I've Spotted at Every Airport From LAX to CPHThese are the only jeans I'll fly in.
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So Many Celeb-Loved Jeans Are On Major Sale RN—These 29 Are the StandoutsLevi's 501s: a Hollywood go-to.
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I'm in My 20s, and Jennifer Aniston Is in Her 50s—We're Both Sidelining Blue Jeans for This Cool 2025 AltYou should too.
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Jennifer Aniston Just Abandoned Her Signature Flip-Flops for These Anti-Trend ShoesNordstrom shoppers love them.
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I'm in My 20s, and Jen Aniston Is in Her 50s, But I'd Wear Her Chic OutfitsA style icon.
