As with many Hollywood stalwarts, Jennifer Aniston’s sartorial journey has been as fun to watch as the roles she’s played. From her early days on Friends to some iconic red carpet appearances (opting for archival designs in recent years), Aniston’s wardrobe has consistently sat somewhere between aspirational glamour and attainable elegance.
Like so many women in the public eye, she has at turns been sexualised and vilified by the media, but now, she is finally being celebrated for her timeless style and decades of staying true to it. And that, my friend, is what they call closure.
Jennifer Aniston wearing a silk, bias-cut, vintage gown by John Galliano for Dior at the 2020 SAG Awards in LA
(Image credit: Jon Kopaloff via Getty Images)
When Rachel Green first appeared in 1994, she quickly became a ’90s style icon, despite her pilot outfit being a gaudy wedding dress complete with a frothy headband-turned-veil. Chiming with the era’s style boom, her influence extended far beyond the sitcom.
There was, of course, “The Rachel”: a layered, casually voluminous haircut that became a literal global sensation and marked a shift away from the Dynasty-style blowouts of the ’80s . “The Rachel”, by contrast, defined a more accessible approach to glamour.
Jennifer Aniston with “The Rachel” haircut
(Image credit: Kevin Mazur Archive 1/WireImage via Getty Images)
Aniston’s ‘girl-next-door’ wardrobe mirrored this same balance of accessibility and aspiration. Silky slip dresses, mini skirts paired with fitted knits or tank tops, knee boots, and relaxed denim were staples that fans could easily emulate. Unlike the polished, glossy looks of the ’80s, this was high style that felt attainable.
Aniston’s wardrobe—on and off-screen—captured the cultural ethos of the time. She became the ultimate cool girl in an era filled with them, and her ’90s wardrobe is now as coveted and mythologised as Carolyn Bessette-Kennedy’s.
Jennifer Aniston in the 1990s
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In the 2000s, when Aniston’s star power went stratospheric, her style became characterised by clean lines and form-fitting gowns, often in neutral or monochrome tones, as she became a regular on the red carpet. Her hair, again, the subject of much discussion, evolved into sleek, straight styles, which, just as “The Rachel” before it, complemented her streamlined wardrobe choices.
Despite this being the period that marked her transition from television star to Hollywood A-lister, she continued to exude an understated elegance. Designers like Versace and Valentino dressed her famously lithe frame in timeless silhouettes, rather than trend-driven shapes—a formula she’s stayed true to.
The 2000s were also a time when celebrity style became increasingly intertwined with branding, as actors began replacing models on magazine covers (Jen, always ahead of the curve, had had her own cover girl debut in 1997). Part of the power of brand Aniston was that her style choices conveyed reliability, elegance, and an aspirational (yet still somewhat accessible) taste.
Jennifer Aniston in the 2000s
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Jennifer Aniston in the 2010s
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In recent years, Aniston’s style has matured into a refined study of modern minimalism. Tailored separates, neutral tones, and layered textures continue to dominate and have made her a poster girl for timelessness at a time when society is grappling with overconsumption and the veracious pace of trend cycles.
At the forefront once more, her wardrobe today reflects a cultural shift towards conscious consumption and longevity over fast-fashion novelty. Even in casual streetwear, there is a precision to what she wears, whether that’s a perfectly cut trench coat, The Row trainers, or a leather jacket.
Jennifer Aniston in the 2020s
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Adaptable, enduring, and always in tune with the times, Jennifer Aniston’s style evolution mirrors her career, from the lovable Rachel Green to the nuanced and complicated Alex Levy in The Morning Show.
Unlike so many celebrities, who cater to the changing whims of fashion, her enduring style lies in its relatability and consistency. It shouldn’t be as unusual as it is, but there is a certain aspirational normalcy that is potently alluring. She’s navigated decades of fashion shifts without losing a sense of self. From the democratised cool of the ’90s to today’s conscious minimalism, her fashion choices feel refreshingly authentic and prove the old adage that the best style comes from cultivating an understanding of one’s own aesthetic.
Shop Jennifer Aniston-Inspired Timeless Wardrobe Staples
MANGO
Kitten-Heel Patent Leather Shoes – Women | Mango United Kingdom
JAMES PERSE
Vintage Boy Cotton-Jersey T-Shirt
ISABEL MARANT
Klyce Leather-Trimmed Suede Sneakers
COS
Slim Exaggerated-Collar Jersey Shirt
ALIGNE
Edie Flare Trouser
Chanel
Pre-Owned 2014-2015 Jumbo Classic Lambskin Double Flap Shoulder Bag
H&M Studio
Wool-Blend Jumper
Halara
Flex™ High Waisted Side Zipper Pocket Work Flare Trousers
THE ROW
Owen Runner Leather and Mesh Sneakers