Gabrielle Union’s Style Evolution: From 10 Things I Hate About You Cheerleader to Prada Wedge Sophisticate

In 1999, Gabrielle Union made one of her earliest on-screen impressions as Chastity Church, the confident, quick-witted cheerleader in 10 Things I Hate About You. Though she played a high school student and Bianca Stratford’s (Larisa Oleynik) best friend, Union was already 25 when the film was shot in 1998.

By the time the teen romantic comedy premiered in March 1999, she had become part of a cultural touchstone that perfectly captured the fashion spirit of the late ’90s—think platform sandals, cropped cardigans, and flirty satin dresses.

That same playful yet polished aesthetic would later evolve into the red-carpet sophistication for which Union is now known. From early Y2K staples to statement luxury pieces like her metallic Prada wedges, she has consistently embraced footwear that blends confidence, comfort, and modern femininity. This signature continues to define her style both on and off screen.

“We spent all of our downtime together and loved it, [and] perhaps I got some fake IDs,” Union recalled in a 2019 interview with ET. “It was just such a special, special time, and I could never recreate that.”

Larisa Oleynik as Bianca Stratford, Gabrielle Union as Chastity Church, and Joseph Gordon-Levitt as Cameron James in the 1999 American teen romantic comedy film 10 Things I Hate About You (Credit: Buena Vista Pictures)

The film also starred Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik. David Krumholtz, who played geek Michael Eckman in the movie, later reflected on how much fun they had filming Heath Ledger’s first American movie.

The Fashion of “10 Things I Hate About You”: Late-’90s Footwear and Teen Style Defined

Before Gabrielle Union’s breakout fashion moments on the red carpet, 10 Things I Hate About You offered a nostalgic snapshot of late-’90s teen style. The movie’s costume design perfectly reflected the era’s footwear trends—from Kat Stratford’s chunky platform sandals to Bianca’s knee-high lace-up boots, each look helping define their contrasting personalities and social roles.

Larisa Oleynik and Julia Stiles capture the essence of late-’90s teen fashion in 10 Things I Hate About You, pairing lace-up suede boots and platform sandals with their contrasting preppy and grunge styles (Credit: Buena Vista Pictures)

“Work was fun, and after work we were inseparable. We laughed, we partied, we rapped. Joseph Gordon-Levitt turned me on to Phish, and I turned him on to Wu-Tang. Gabrielle Union had us in stitches, Julia Stiles brought her own brand of Soho-bred artistic intellectualism (at only 17, mind you), Larisa Oleynik’s laughter filled the room, and we marveled at the tonedness of Andrew Keegan’s muscles (a great sport!),” David Krumholtz wrote in Vulture in 2015.

The same year, Gabrielle starred in the 1999 American teen romantic comedy film She’s All That. Following her success in 10 Things I Hate About You and She’s All That, Gabrielle Union continued to captivate audiences with her charm and talent.

While she has built an impressive career on-screen, Union has become a style icon, consistently turning heads with her fashion choices. One such occasion was in June 2016, when she stepped out in a stunning ensemble that perfectly showcased her sophisticated style.

A Night of Style: Gabrielle Union’s ASOS Jumpsuit and Prada Wedges

Gabrielle Union stuns in a chic navy blue jumpsuit adorned with gold grommets at the launch of the new Jaguar XE on June 16, 2016, at The Collection in Coral Gables in Miami, Florida (Credit: Johnny Louis / WENN)

Gabrielle Union supported her husband as he launched two new Jaguar models in Miami, Florida. She married NBA star Dwyane Wade in 2014. They met in 2007 while cohosting a sponsored Super Bowl party.

Gabrielle Union stuns in a plunging navy ASOS jumpsuit paired with metallic gold Prada wedges at the Jaguar XE launch event

Gabrielle attended the launch event in a sexy $55 navy blue jumpsuit from ASOS. The trendy (and affordable!) piece featured a plunging, grommet-adorned neck, waistline, and subtle cutouts at the arms.

Gabrielle accessorized her look with a yellow embroidered clutch and a pair of metallic, perforated Prada wedges.

The Bring It On actress spent the entire evening by her husband’s side, sporting a giant smile as she supported him in his business endeavors.

Gabrielle Union supports her husband, Dwyane Wade, as he launches the new Jaguar XE at The Collection in Coral Gables

👠 More Prada Wedge Moments to Explore

Prada’s wedge heels have long balanced bold design with timeless sophistication. From flame-detailed statement pieces to everyday suede platforms, these celebrity looks showcase how the Italian fashion house keeps wedges effortlessly stylish season after season.

Gabrielle Union’s feet shine in metallic gold Prada wedges, featuring a bold perforated design, at the Jaguar XE launch event

Prada’s Perforated Wedges: A Fashion Must-Have

Prada always creates the most exciting wedge styles, even though we have to pay homage to Chanel for first creating the gun-themed heels. You can check out this perforated metallic pair at Nordstrom and Farfetch.

Prada Perforated Metallic Wedge Sandals, $447

Before You Go: Dive Into Gabrielle Union’s Signature Footwear Looks

From her early acting days in 10 Things I Hate About You to her sophisticated red-carpet appearances, Gabrielle Union has proven that great style—and even greater shoes—never go out of fashion. Dive into more of her standout looks below.