I Re-Created Jennifer Aniston's Most Iconic 1990s Outfits

Jennifer Aniston 1990s outfits


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Every time we bring up the topic of '90s style, it's not long before someone drops Jennifer Aniston's name. Her style is so synonymous with '90s fashion that it'd be hard not to give her a mention. These days, we've mentioned the decade quite a bit since its über-minimalistic aesthetic has continued to hold an influence on fashion two decades (and counting) later.

Pluck out any of the biggest 2019 trends at random—strappy sandals, cargo pants, baby tees, I could go on—and chances are Jennifer Aniston wore the trend first and better. From her days playing Rachel Green on-screen to her red carpet appearances, Jennifer Aniston's 1990s outfits are a treasure trove of throwback style that feels just as nostalgic as it does cool right now. To prove it, I went ahead and used current pieces to re-create her most iconic style moments from the decade to show you how timeless those looks really are. Keep reading to fill up on inspiration from our friend Jen, see my versions of her best outfits, and then shop pieces to get the looks for yourself.

The Baby Tee and Slip Dress Look, 1996
Jennifer Aniston outfits


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Before we dive into Jen's dressier looks, let's just take moment to appreciate her off-duty style. Remember when she taught us how to layer a slip dress over a T-shirt (and made her Walkman headphones into the chicest accessory of the decade)?

On me: Lacausa Frank Tee ($48); Urban Outfitters dress; vintage shirt; Krewe Ward Sunglasses ($275); Converse Golf Le Fleur sneakers

The Cargo Pants and Flip Flops Look, 1999
Jennifer Aniston's best 1990s outfits


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Revisiting this Jen and Brad street style moment from back in the day (remember when the two were a thing?) has me convinced that Aniston predicted all the major trends of this summer 20 years prior. Her ribbed tank top, cargo-style pants, and fli- flops are all styles we've written about extensively this year.

The Low-Rise Red Carpet Look, 1999
Jennifer Aniston's most iconic '90s looks


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Tube tops! Low rises! Maxi skirts! We'd never see a red carpet look like this in 2019, but that's arguably what makes this Jennifer Aniston look so, well, nostalgic. 

On me: Babaton Essamba Tube Top ($48); Amber Sceats pearl necklace; Realisation Naomi Skirt ($180)

The Strappy LBD Look, 1997
Jennifer Aniston '90s outfits


Dave Allocca/Getty Images

Last, but certainly not least is the look I most associate with '90s-era Jen. This slinky black dress and barely there sandals are peak minimalist, but although this look has the '90s written all over it, it's just as relevant today.

On me: vintage dress; Cinco Monique Necklace ($65); vintage Stuart Weitzman heels; Amber Sceats Evan Anklet ($69)

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