Drew Barrymore’s Best ‘90s Fashion Moments

Drew Barrymore started the decade off at just 15 years old attending the 1990 screening of Longtime Companion in Los Angeles. She wore a white T-shirt styled with a leather motorcycle jacket, high-waisted black jean shorts, and leather boots.

Barrymore was all for making a statement even during her early years. At the 1990 Total Recall party, she wore a f*ck-printed fanny pack with a black vest and denim shorts.

Wearing a red polka-dot crop top, straight blue jeans, and black Converse sneakers to the 1990 premiere of The Freshman.

The teen actress attended the 1990 Marked For Death premiere rocking a floral mini dress with a leather jacket and black velvet oxfords.

Wearing a cropped ivory cardigan and ripped light-washed jeans to the 1991 Guilty by Suspicion premiere.

While attending the E.T. Adventure Ride grand opening celebration in 1991, Barrymore was seen in a mauve-colored jacket with a white top, baggy blue jeans, and brown sunglasses.

The actress was captured in a flowy button-down top with dark-washed jeans and black shoes to The Indian Runner premiere in Los Angeles.

The actress wore a black blazer with an oversized white collared top peaking underneath to the 1992 Rita Hayworth Gala in New York City. She then styled her look with a slit-adorned maxi skirt and black shoes.

Barrymore was spotted at the 1992 Cannes Film Festival opting for a ‘60s mod-inspired color block mini dress with black flats.

Wearing a blazer-jean combo with a white top and black loafers during the 1992 CBS Press Tour. She also wore a chunky headband, black sunglasses, and carried a leather mini bag.

Barrymore attended the 1992 premiere of Reservoir Dogs in Los Angeles wearing a black blazer with cuffed denim shorts and heeled oxfords.

The actress went full-on oversized in a denim jacket over a gray top and navy bottoms, which she styled with black boots and a gold necklace.

Barrymore channeled Hollywood glamour in a simple yet stunning black maxi gown with matching heels and a white choker necklace.

In 1993, Barrymore attended the Los Angeles premiere of Sliver rocking a dark-washed denim jacket over a white top and black pants. She completed her red carpet look with a Mickey Mouse shoulder bag and blue-tinted shades.

Barrymore looked darling at the 1993 Billboard Music Awards in a silver slip dress, a white choker, and black heels.

In 1994, Barrymore was photographed wearing a black button-up jacket over a green mini skirt, paired with knee-high boots and a backpack.

Barrymore went for the ultimate tomboy look back in ‘95 at the premiere of Tommy Boy in Los Angeles, opting for a striped sweater with black low-rise jeans and boots.

Wearing a satin white mini dress with black T-strap heels to the 1995 Indiscretions premiere in New York City.

Barrymore channeled her inner Marilyn Monroe at the 1995 MTV VMAs in a head-turning strapless black gown and a platinum blonde wig with daisies.

Barrymore switches it up in New York City rocking a white blouse paired with corduroy pants, a fleece jacket, embroidered scarf, and brown boots.

Rocking a white slip dress with a silk floral jacket and black heels at the 1996 From Dusk Till Dawn premiere in Los Angeles.

Barrymore wore head-to-toe black with a studded floral handbag during the Los Angeles premiere of Beautiful Girls in 1996.

The actress gave peace signs at MTV’s Choose or Lose event in 1996 wearing a black and navy outfit with floral motifs.

Barrymore was spotted at the Gala Evening in Los Angeles wearing a pale yellow maxi dress.

The then-22-year-old actress attended the 1997 Scream premiere in London donning a strappy chevron-printed gown.

In 1997, Barrymore was photographed at “A Time For Heroes” Elizabeth Glaser Pediatric AIDS Foundation Benefit wearing a blue button-down top, bootcut jeans, and blue slides.

Barrymore was rocking the sparkly mini bag trend even in 1998 at Premiere Magazine’s “Women In Hollywood” luncheon in Los Angeles. She also wore a gray top with a velvet midi skirt and black heels.

Wearing a black floral-embroidered dress to the 1998 premiere of The Wedding Singer in New York City.

Barrymore wore a floral wrap dress and black pumps while attending the Rolling Stones concert held at the Hard Rock Hotel.

The Ever After actress attended the 1998 Oscars in a black maxi gown with white flowers pinned to her hair.

Wearing a paisley midi dress with an oversized blazer and black sandals to the 1998 Kids’ Choice Awards in Los Angeles.

In 1998, Barrymore wore a stunning printed gown to the Ever After Gala held in Florence.

The actress arrived at the premiere of her film Home Fries wearing a strapless scarlet-colored gown and black sandals.

In 1998, Barrymore was spotted at the Premiere Magazine’s “Women In Hollywood” luncheon wearing a white button-down short tucked into a black midi skirt and paired with platform heels and a leather handbag.

Barrymore’s boho-inspired look at the 1999 Kids’ Choice Awards included a black quarter-sleeve top with a denim maxi skirt, a red scarf, and a headband.

The actress made an appearance at the 1999 Blockbuster Entertainment Awards opting for a fitted long blazer and pants set, styled with a white top and strappy sandals.

In 1999, the Never Been Kissed star attended the “Women in Film” Crystal Awards rocking a green midi skirt, which she paired with a white blouse, oversized blazer, and platform strappy heels.

While attending the premiere of Blue Streak, Barrymore wore a black see-through long sleeve shirt with a gray midi skirt, black sandals, and a leather bag.

The actress arrived at the red carpet premiere for Dog Park wearing a gray long sleeve top with a black skirt, sandals, and a leather handbag.

Barrymore was captured hand-in-hand with actress Molly Shannon at Saturday Night Live’s 25th Anniversary celebration, wearing a crochet poncho top with a tank underneath, a shimmery periwinkle skirt, and blue metallic flats.