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


(Image credit: Dave Allocca/Getty Images)

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
(Image credit: Mitchell Gerber/Getty Images )

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)?


My take
(Image credit: @anna__laplaca)

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
(Image credit: Bauer-Griffin/Getty Images)

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.


My take
(Image credit: @anna__laplaca)

On me: Hanes Ribbed Tank Top ($10); Zara cargo pants; Ancient Greek Sandals Thalia Flat Sandals ($126); Building Block Box Bag ($322)


The Low-Rise Red Carpet Look, 1999
(Image credit: Ron Galella/Getty Images)

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. 


My take
(Image credit: @anna__laplaca)

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


The Strappy LBD Look, 1997
(Image credit: 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.


My take
(Image credit: @anna__laplaca)

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

For even more throwback celeb looks, may I direct your attention to these iconic J.Lo airport outfits from the '90s?

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.