Jennifer Aniston’s ’90s Style Is A Joy To Look At – And Here’s Where You Can Get The Look, Too

It's time to make Friends with flatform sandals, vest tops and lots of LBDs...

Jennifer Aniston '90s style

by Laura Antonia Jordan |

My brain’s capacity to forget birthdays, passwords and names yet store a limitless glut of useless information never ceases to amaze me. For example, I have invested a disproportionate amount of mental real estate recently to thinking about an image of Jennifer Aniston shopping on Rodeo Drive with Brad Pitt in 1999. Like I said, useless.

Jennifer Aniston 90s style
Jennifer Aniston in 1999 ©Getty

But, hang on, is this intel really that redundant? From a style perspective, perhaps not (although still not an excuse for forgetting your birthday, Dad – sorry). Consider how right this over 20-year old look feels now. There’s the simple vest top, the zingy, not-too-loose cargo pants, the simple belt bag. There’s the small, but not comedically micro sunglasses and best of all, the flatform flipflops which are a dead ringer for The Row’s sell-out Ginza sandals. It’s not hard to imagine a slew of young Hollywood stars and fashion 'It' girls wearing this exact look today.

Jennifer Aniston 90s style
Jennifer Aniston and Brad Pitt 1999 ©Getty

Indeed, Aniston’s ’90s fashion back catalogue is worth a relook, and not only if you’re old enough to have got a botch job Rachel cut (yep, guilty) and coveted everything she wore in Friends. As our love affair with all things ’90s continues to endure, we should note that the secret to Aniston’s enduring fashion resonance – and the reason why her looks feel relevant rather than quaintly retro – is the simplicity. Pared-back style has always been her calling card. She is a Cali girl through and through, and has always mastered that mix of ease and gloss to perfection (she’s laidback, but not pyjamas and Uggs to Erewhon horizontal).

Aniston is the OG of laidback ’90s style. There’s a lot to covet in her throwback off-duty wardrobe now: mom jeans, sheer shirts, slip dresses, dinky handbags, bucket hats and block heeled boots. Those chunky-soled sandals are so good they really are worth another shout out. You’ve probably seen a lot of this stuff on Instagram already.

Jennifer Aniston 90s style
Jennifer Aniston 1998 ©Getty

On the red carpet, Aniston’s ’90s style is equally minimal: slip dresses, neutral separates, barely-there sandals, pouch bags, tailored trousers. The handkerchief top she wore to the SAG Awards in 1999, feels very now; as do the elbow length gloves and strapless gown worn to the Emmy’s in 1995. In fact, I would love to get stats on how many black dresses she has worn over the years. Answer: a lot, you can never go wrong with an LBD.

Jennifer Aniston 90s style
Jennifer Aniston and Courtney Cox 1999 ©Getty

Here’s how to get the Jen An ’90s look this summer:


SHOP: Jen An's 90s Look

Arket, Oversized Leather Blazer, £290
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Joseph, Silk Satin Clea Dress, £445
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By Far, Amber Scarlet Semi-Patent Leather, £500
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Ganni, Melange Knit Mini Dress, £155
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Weekday, Stella Tank Top, £8
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Totu00eame, Loose-Fit Denim Distressed Light Blue, £280
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& Other Stories, Cropped Criss-Cross Tie Blouse, £65
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Daily Paper, Pistache Green Laaziah Blazer, £215
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Missoma, Baroque Pearl Twisted Link Necklace, £259
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But Cali girls do love a bit of boho, so there’s the occasional curve ball like a ritzy crochet cardigan (also back this summer) and bra worn in 1995 and the dress she wore to the Emmy’s in 1999 with an ornately embroidered bodice. Again, that West Coast ease is there though as her Rachel hair was teased in just-back-from-a-surf tousled waves.

Jennifer Aniston 90s style
Jennifer Aniston 1999 ©Getty

When Aniston wore that vintage John Galliano for Christian Dior white bias-cut dress to the SAG Awards in January (a 1999 design picked up a luxury Beverly Hills vintage boutique LILY et Cie. ‘We have a long-standing relationship with Jennifer and her team, and they’ve looked to LILY et Cie for special moments in the past,’ owner Rita Watnick told Grazia at the time), it felt like a meta style move. She stole the show in something you could easily have seen her wearing the first time around, and looked more modern than anyone else on the red carpet in the process. Aniston has always known what works for her.

Jennifer Aniston 90s style
Jennifer Aniston 1998 ©Getty

I wrote for Grazia around Aniston’s 50th birthday how I once saw her at The Sunset Tower hotel bar in LA. I had always thought that old adage about someone ‘lighting up the room’ was a cliché, but she does indeed possess that luminous, mega-watt charisma of a real star. What was she wearing? I don’t remember – and that’s a compliment. Because, like only the truly stylish, she has always worn the clothes, and not the other way around.

READ MORE: The Workwear Lessons We Can (Still) All Learn From Rachel Green

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