1 1989: Miss Firecracker Premiere
Steve.Granitz//Getty Images The voluminous hair, the oversized suit jacket, the barely-there bottoms—how cool is Roberts?
21989: Great Balls of Fire!Premiere
Steve.Granitz//Getty Images The Hollywood actress stepped out at the Great Balls of Fire! premiere in a cozy getup consisting of an ivory cable knit sweater, biker shorts, and knee-high boots. It's a look that's still trendy today.
31989: Back to the Future Part II Premiere
Ron Galella, Ltd.//Getty Images Hat's off to Roberts! The screen actor held hands with Alan Greisman in a velvet vest, pleated taupe pants, and an oversized hat. The look screams "late-80s," in all of the best ways.
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41990: Gray Suiting at the Golden Globes
Steve.Granitz//Getty Images Roberts mastered the art of suiting in the 1990s. The star held her Golden Globe award while wearing a grayish two-piece set, a crisp white blouse, and a purple patterned tie.
51990: Another Vest
Steve.Granitz//Getty Images Roberts always looks her best in vests. Here, she wore a tan one paired with a gray-green maxi skirt.
61991: Floral Frock
Ron Galella//Getty Images Roberts enjoyed lunch at The Morgan Hotel in New York City in a floral frock with thick white socks and patent leather loafers.
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71992: Traveling in Style
Tom Wargacki//Getty Images She even looked cool in transit. The star arrived at Heathrow Airport in the early '90s in faded denim jeans, a slouchy maroon cardigan, sunglasses, and a black beret.
81993: A Velvet Look
Ron Davis//Getty Images Roberts posed at the Screen Actors' Guild Awards in a green and floral-trimmed velvet number. The gold buttons and oversized cuffs provided the perfect amount of je nais se quoi.
91993: Pinstripes and Smiles
Ron Galella, Ltd.//Getty Images Another event, another two-piece set. The star smiled at the Short Cuts screening in a black and white pinstriped outfit with a button-down white blouse and pearls.
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101994: Tinted Shades
Ron Galella//Getty Images Roberts embraced another velvet ensemble when she arrived at the world premiere of Crooklyn in a velvet blazer with black slacks and shades.
111995: Out and About
Ron Galella, Ltd.//Getty Images The star always keeps it cool. She was snapped in New York City wearing striped pants, a white top, an oversized black sweater, and sunglasses.
121997: '90s Dressing
Kevin.Mazur//Getty Images Roberts flaunted '90s florals at a Rainforest Foundation benefit over twenty years ago. She also included some popular Y2K accessories, like platform sandals and a choker necklace.
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131998: Chocolate Brown Gown
TV Times//Getty Images She looked like a dream in a chocolate brown long-sleeved gown paired with loose curls and coral lipstick at the BAFTA Film Awards.
141998: Embroidered Elegance
Fairchild Archive//Getty Images Roberts stunned on the Golden Globes red carpet in a bold embroidered look accessorized with pointed-toe heels.
151998: Cat-Eye Shades
Jim Smeal//Getty Images Roberts and co-star Rupert Everett showed off their cool sides when they rolled up to the Blockbuster Awards in matching cat-eye sunglasses.
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161998: Stepmom Premiere
Ron Galella//Getty Images Between the pink strapless gown and the furry black stole, Roberts' look to the New York City premiere of Stepmom was pure glamour.
17 1999: Say it with Sequins
Fred Duval//Getty Images The star brightly stood out in sequins when she walked into the Notting Hill London premiere in a bedazzled pink dress.
18 1999: Elegant at the Emmys
Steve.Granitz//Getty Images That same year, she wore a strappy black gown and a chic updo to the Emmy Awards.
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192001: Patent Leather and Plaid
Steve Granitz//Getty Images Roberts proved more is, well, more, when she arrived at the L.A. Film Critics Awards in a patent leather pink jacket, plaid skirt, and shiny knee-high boots. The maximalist look was everything you'd want in a fun outfit and then some.
202001: Mexican Premiere
Jeff Kravitz//Getty Images How cool were the croc-embossed pants Roberts wore to the Los Angeles premiere of Mexican?
Brittany is a freelance writer based in her hometown of New York City. She writes about everything from fashion and beauty to food and wellness. When she's not writing, she can often be found at her local library, playing with her cats, or exploring the Metropolitan Museum of Art.
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