25 Years Ago, Jennifer Aniston Wore Her Most Underrated Look

There’s no shortage of Jennifer Aniston’s style roundups — and for good reason. Since the ’90s, the Friends superstar has become one of the biggest fashion icons of her generation, on- and off-screen. Style savants loved the fictional Rachel Green for her trendy looks, with the likes of Taylor Swift inadvertently recreating her outfits to this day.

Meanwhile, those who geared more classic in their style sensibilities had Aniston to emulate. The actor was lauded for her timeless aesthetic, ever choosing minimalist pieces that transcend style eras. Case in point: the black ensemble she wore to the 1999 Screen Actors Guild Awards — her most underrated look of all time, IMHO.

Jennifer’s Crop Top & Skirt

On March 7, 1999, the entire cast of Friends pulled up, perfectly coordinated, to the SAG Awards. The group was nominated for Outstanding Performance by an Ensemble in a Comedy Series. It’s unclear if they matched on purpose, but all six actors wore black ensembles that reeked of style. Aniston’s, however, was easily the most fashion-forward of the bunch.

Evoking the decade’s style sensibilities, Aniston wore a strapless, bandana-style crop top — one of the biggest ’90s trends at the time. While fashion girls back then typically utilized colorful scarves and handkerchiefs with the loudest prints, Aniston kept hers simple in plain black.

She paired the silken item with a maxi skirt, complete with chunky pleats and a low-rise hem — another style evocative of the era. Despite both pieces of her co-ord set skewing the trendy route, her take in classic noir made the look feel timeless and elegant.

Special Mention: Her Polished ’Do

Her hair was as sleek as her ’fit, of course. Aniston kept her glam just as effortless with barely-there makeup and subtly glossy lips. Her entire beauty look served as the perfect neutral backdrop, against which her diamond-encrusted necklace sparkled.

Aniston’s ’90s style is so underrated.