Drew Barrymore was a rising Hollywood star at the start of the ‘90s. She first garnered fame for her role in
E.T. the Extra-Terrestrial (1982) and has been featured in some of the following decade’s cult classic films, like Poison Ivy (1992), Scream (1996), and Never Been Kissed (1999). Barrymore even became a fashion favorite around the same time, starring in coveted campaigns for Guess in 1993 and Miu Miu in 1995, just to name a few.
Her style has always embodied a sense of confidence and following her own fashion rules, as she’d arrive at the industry’s biggest events in a leather jacket and ripped denim shorts, paired with statement accessories and a cigarette in hand. She also was a prime example of ‘90s-era grunge, sticking with her favorite wardrobe staples like combat boots, chokers, and baggy jeans with her go-to choice of dark lipstick. But Barrymore also put a girly spin on her off-screen outfits, as she remained a fan of silky slip dresses, mini bags, and her signature daisy floral accents by the end of the decade.
Take a scroll through Drew Barrymore’s ‘90s style evolution, ahead.
1990, Longtime Companion Screening Jim Smeal/Ron Galella Collection/Getty Images
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. 1990, Total Recall Party Jim Smeal/Ron Galella Collection/Getty Images
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. 1990, The Freshman Premiere Ron Galella/Ron Galella Collection/Getty Images
Wearing a red polka-dot crop top, straight blue jeans, and black Converse sneakers to the 1990 premiere of
The Freshman. 1990, Marked For Death Premiere Ron Galella/Ron Galella Collection/Getty Images
The teen actress attended the 1990
Marked For Death premiere rocking a floral mini dress with a leather jacket and black velvet oxfords. 1991, Guilty by Suspicion Premiere Ron Galella/Ron Galella Collection/Getty Images
Wearing a cropped ivory cardigan and ripped light-washed jeans to the 1991
Guilty by Suspicion premiere. 1991, E.T. Adventure Ride Grand Opening Celebration Ron Galella, Ltd./Ron Galella Collection/Getty Images
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. 1991, The Indian Runner Premiere Ron Galella/Ron Galella Collection/Getty Images
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. 1992, Rita Hayworth Gala Images Press/Archive Photos/Getty Images
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.
1992, Cannes Film Festival Pool ARNAL/GARCIA/PICOT/Gamma-Rapho/Getty Images
Barrymore was spotted at the 1992 Cannes Film Festival opting for a ‘60s mod-inspired color block mini dress with black flats.
1992, CBS Press Tour Ron Galella/Ron Galella Collection/Getty Images
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.
1992, Reservoir Dogs Premiere Jim Smeal/Ron Galella Collection/Getty Images
Barrymore attended the 1992 premiere of
Reservoir Dogs in Los Angeles wearing a black blazer with cuffed denim shorts and heeled oxfords. 1993, Golden Globe Awards Ron Galella/Ron Galella Collection/Getty Images
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.
1993, Golden Globe Awards Frank Trapper/Corbis Historical/Getty Images
Barrymore channeled Hollywood glamour in a simple yet stunning black maxi gown with matching heels and a white choker necklace.
1993, Sliver Premiere Steve.Granitz/WireImage/Getty Images
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. 1993, Billboard Music Awards Ron Davis/Archive Photos/Getty Images
Barrymore looked darling at the 1993 Billboard Music Awards in a silver slip dress, a white choker, and black heels.
1994, Street Sighting Michael Ochs Archives/Michael Ochs Archives/Getty Images
In 1994, Barrymore was photographed wearing a black button-up jacket over a green mini skirt, paired with knee-high boots and a backpack.
1995, Tommy Boy Premiere Jim Smeal/Ron Galella Collection/Getty Images
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. 1995, Indiscretions Premiere Ron Galella/Ron Galella Collection/Getty Images
Wearing a satin white mini dress with black T-strap heels to the 1995
Indiscretions premiere in New York City. 1995, MTV VMAs Ron Galella, Ltd./Ron Galella Collection/Getty Images
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.
1995, New York City Ron Galella, Ltd./Ron Galella Collection/Getty Images
Barrymore switches it up in New York City rocking a white blouse paired with corduroy pants, a fleece jacket, embroidered scarf, and brown boots.
1996, From Dusk Till Dawn Premiere Steve.Granitz/WireImage/Getty Images
Rocking a white slip dress with a silk floral jacket and black heels at the 1996
From Dusk Till Dawn premiere in Los Angeles. 1996, Beautiful Girls Premiere Jim Smeal/Ron Galella Collection/Getty Images
Barrymore wore head-to-toe black with a studded floral handbag during the Los Angeles premiere of
Beautiful Girls in 1996. 1996, MTV Choose or Lose Event Michael Ochs Archives/Michael Ochs Archives/Getty Images
The actress gave peace signs at MTV’s
Choose or Lose event in 1996 wearing a black and navy outfit with floral motifs. 1996, Gala Evening Frank Trapper/Corbis Entertainment/Getty Images
Barrymore was spotted at the Gala Evening in Los Angeles wearing a pale yellow maxi dress.
1997, Scream Premiere Tom Wargacki/WireImage/Getty Images
The then-22-year-old actress attended the 1997
Scream premiere in London donning a strappy chevron-printed gown. 1997, “A Time For Heroes” Elizabeth Glaser Pediatric AIDS Foundation Benefit Steve.Granitz/WireImage/Getty Images
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.
1998, Premiere Magazine’s “Women In Hollywood” Luncheon Jim Smeal/Ron Galella Collection/Getty Images
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. 1998, The Wedding Singer Premiere Ron Galella, Ltd./Ron Galella Collection/Getty Images
Wearing a black floral-embroidered dress to the 1998 premiere of
The Wedding Singer in New York City. 1998, Rolling Stones Concert Frank Trapper/Corbis Entertainment/Getty Images
Barrymore wore a floral wrap dress and black pumps while attending the Rolling Stones concert held at the Hard Rock Hotel.
1998, Oscars Frank Trapper/Corbis Entertainment/Getty Images
Ever After actress attended the 1998 Oscars in a black maxi gown with white flowers pinned to her hair. 1998, Kids’ Choice Awards Jeff Kravitz/FilmMagic, Inc/Getty Images
Wearing a paisley midi dress with an oversized blazer and black sandals to the 1998 Kids’ Choice Awards in Los Angeles.
1998, The Ever After Gala Eric Robert/Sygma/Getty Images
In 1998, Barrymore wore a stunning printed gown to the
Ever After Gala held in Florence. 1998, Home Fries Premiere Frank Trapper/Corbis Entertainment/Getty Images
The actress arrived at the premiere of her film
Home Fries wearing a strapless scarlet-colored gown and black sandals. 1998, Premiere Magazine’s “Women In Hollywood” Luncheon Steve Granitz/WireImage/Getty Images
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. 1999, Kids’ Choice Awards Jeff Kravitz/FilmMagic, Inc/Getty Images
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.
1999, Blockbuster Entertainment Awards Frank Trapper/Corbis Entertainment/Getty Images
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.
1999, “Women in Film” Crystal Awards Steve Granitz/WireImage/Getty Images
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. 1999, Blue Streak Premiere Denny Keeler/Hulton Archive/Getty Images
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. 1999, Dog Park Premiere Sam Levi/WireImage/Getty Images
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. 1999, Saturday Night Live’s 25th Anniversary Celebration Ron Galella/Ron Galella Collection/Getty Images
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. See more ‘90s fashion moments from Janet Jackson, Pamela Anderson, and Winona Ryder. Style + Culture, delivered straight to your inbox.