Right at the start of the decade, Gwyneth Paltrow was seen with actress Winona Ryder. The duo rocked an all-black look with Paltrow wearing a black tee and maxi skirt combo. She finished it with black sneakers and a black jacket.

You can never go wrong with black. Paltrow contrasted her white tee with an oversized black leather blazer, paired with tights and combat boots.

Paltrow shined in Paris wearing an ivory silk slip dress with a matching cover-up draped over her arms.

What would the ‘90s be without this former “It” couple? Paltrow, holding hands with Brad Pitt, rocked a black button-up mini dress and black strapped pumps.

Paltrow went minimally chic at the 1995 Met Gala. She wore form-fitting baby blue tank dress designed by Calvin Klein and black pumps.

Back in ‘95, the actress stepped out in a basic white tee teamed with a velvet black suit and heeled loafers.

Paltrow shines wherever she is, even in black. The actress went simple and wore a classic black maxi dress and strappy black heels for the 1996 Emma premiere.

Paltrow perfected the relaxed look throughout the decade, especially at this premiere. The star wore a black two-piece set with a leopard-print coat and her go-to Converse sneakers.

Paltrow somehow makes casual look ultra-chic. She dressed in a black long-sleeved top tucked into leather trousers. She finished the look with simple black boots.

Paltrow served a different (and super iconic) look at the 19976 MTV VMAs. Instead of her go-to black-and-white combo, the actress wore a red velvet suit by Tom Ford for Gucci with a barely-buttoned blue top and matching velvet platform boots. This look was brought back by Alessandro Michele for Gucci nearly 25 years later.

Some things just never go out of style. The actress arrived at The Pallbearer premiere and wore a white floor-length buttoned dress and black heels.

The former couple went casual while on the set of Pitt’s 1996 film The Devil Own’s. Paltrow’s off-duty look included jeans and a tee with a leather jacket from Calvin Klein. She also wore Converse sneakers and a still-trendy nylon tote by Prada.

The actress attended the Hard Eight premiere and stunned in a floral mauve outfit, with fur detailing lined at the collar. She completed the look with none other than classic black heels.

Paltrow wore a matching beige sweater-and-scarf combo with black leather bottoms.

At the 1997 Boogie Nights premiere, Paltrow was seen living it up in an all-black outfit. She appeared in a simple tank, baggy pants, and Adidas Gazelles.

Paltrow strutted into January 1998 wearing a spaghetti-strapped black dress from Donna Karan. She paired it with strappy kitten heels and wrapped herself in a giant black scarf.

Paltrow took airport fashion to the next level. The movie star left Los Angeles in a matching set, with a gray sweater and the iconic monogrammed Louis Vuitton duffle bag. She wore pearls and black sunglasses, too.

At a Beck concert in 1998, Paltrow posed in a gray cami top and beige linen midi skirt. She accessorized with strappy kitten heels and a mini bag in hand.

Paltrow looked oh-so stunning at the 1999 Golden Globe Awards wearing a metallic skirt and a black cardigan-and-top combo.

Not only did the movie star snag the award for best actress at the 1999 Oscar Awards, but Paltrow also managed to wear one of the best red carpet looks of all time. On this special occasion, the actress dazzled in a bubblegum pink custom gown crafted by Ralph Lauren.

Brunette Gwyn was such an era. The actress arrived at the premiere of her movie The Talented Mr. Ripley wearing a printed navy-and-white midi dress. She completed the look with black strappy heels.