Audrey Hepburn
In the early 90s, most celebrities opted for black and pearl–colored outfits to save them from fashion blunders. But the 1960s style icon Audrey Hepburn chose to surprise the public as she put on a pink one-shoulder full-length gown for the 1992 Oscars. The dress was both unusual and neat and would definitely look great at modern-day red carpet events.
Winona Ryder
According to the legend, Winona Ryder bought the romantic body-fit gown with a sparkly fringe at a thrift shop, and it cost only ten dollars. Whether it's true or not, the outfit looked charming on the actress who definitely stole the spotlight at the 1994 Academy Awards.
Claudia Schiffer
At the 1995 Oscars, Claudia Schiffer wore a stunning fairy tale princess–inspired dress. The classic V-shaped neckline and maxi length did not look boring at all since the gown's glittery fabric of an unusual light purple shade was the perfect match for the model's skin tone and blonde hair.
Uma Thurman
This is another look from the 1995 awards night that left its mark in the history of red carpet attire: Uma Thurman attended the Oscars in a lilac Prada dress with a sheer chiffon wrap. The outfit was different from the usual studio-approved designs that Hollywood actresses normally put on for film events: Thurman's dress was neither predictable nor over-the-top and was associated with high fashion, above all else. In that respect, the actress set a new trend for Oscars' celebrity attire — and today, more than 25 years after the night, movie stars still follow in her footsteps.
Celine Dion
In the 2000s and 2010s, we saw dozens of celebs wearing gold gowns at the Oscars, but at the turn of the century, silver was in fashion. Every detail of the outfit had to be the same matching silver color — and Celine Dion was the one star who nailed the look perfectly in the slinky maxi-length dress she wore at the 1997 Academy Awards.
Cher
The legendary singer was a pioneer of "nude looks" long before the Kardashians. At the 1998 Oscars, Cher donned a see-through outfit teamed with a matching headpiece and choker, and the look was both edgy and elegant.
Halle Berry
In the late 90s, Halle Berry had no idea she would play Catwoman in seductive leather outfits — back then, her style was tender and feminine. The actress' attire at the 1998 Academy Awards is a great example of how a classic cut can look interesting — for example, when decorated with asymmetrical lace inserts. Paired with a messy updo, Berry's look at the night was anything but ordinary.
Tyra Banks
Supermodel Tyra Banks slayed the red carpet in a gorgeous off-the-shoulder dress, paired with a long, creamy shawl. Her outfit at the 1998 Oscars was rather "serious" and lacking any flashy or superfluous detail, but it looked just splendid on Banks.
Gwyneth Paltrow
At the 1999 Oscars, Gwyneth Paltrow turned into a sweet princess in a long bubblegum-colored gown. Thin straps emphasized the actress' delicate shoulders, while her sleek hairdo and the diamond necklace added to the elegance of the overall look.
Jennifer Lopez
With this outfit from the 1999 Academy Awards, Jennifer Lopez proved that amazing red carpet attire does not need to be bright. The star glowed in the black maxi-length gown adorned with sparkly details, and the stunning look was accentuated with several matching jewelry pieces.