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.