Then and WOW: Regina King

Since making her screen debut in 1985 with the hit TV sitcom 227 Regina King has built one of the most exciting and varied careers in Hollywood. King spent decades developing a solid resume with films like Boyz In The Hood, Poetic Justice, Friday, Jerry Maguire and Ray, as well as the acclaimed TV drama Southland. However, it wasn’t until her two-time Emmy Award-winning turn in the critically celebrated anthology series American Crime in 2015 that the star became an award show mainstay.

Since then, King has gone on to win two additional Emmys, a Golden Globe and an Academy Award. With trophy-grabbing projects like If Beale Street Could Talk, Watchmen and Seven Seconds under her belt, it’s safe to say she is now one of the most praised actresses of her generation. As a result, you’d be hard-pressed to find a major red carpet without her on it. King has always shined at events with her modern style, but now she regularly makes ‘best dressed’ lists for rocking stunning designer goods. 

With the help of stylists Wayman Bannerman and Micah McDonald—who also tout Tessa Thompson, Logan Browning and Lizzy Caplan as clients—the star has become synonymous with structured, shoulder-baring gowns. As her style has become more streamlined, so has her use of jewelry. Pretty, minimal pieces have given way to massive, dazzling items that complete her looks. “Regina sends a message of strength,” Bannerman told People in 2019. “Regina is a force and we believe she exudes that on the carpet.” With the star garnering numerous accolades for her directorial debut One Night In Miami, fans are enjoying another award season chock full of show-stopping fashion moments from King.

Check out these Regina King looks that highlight just how much her style has upped its wow factor over the years.

WOW: Old Hollywood Glamour at the 2020 Academy Awards

If there’s ever a time to make a red carpet splash, it’s at the Academy Awards. A presenter at the 92nd annual ceremony, Regina showed up looking like the night’s biggest star, clad in a stunning single-strap powder pink Versace gown embellished with silver and pink crystals that glistened under the flashing lights. Of course, because you can never go too big at the Oscars, it came with a lengthy train that swayed over the star’s Stuart Weitzman shoes and down the arrivals line. While King may have refrained from decorating her neck, that doesn’t mean she skimped on the jewels. In fact, the actress paired over $500,000 worth of Harry Winston jewelry with her fitted gown, including the jeweler’s quintessential five-row diamond tennis bracelet with a tasseled centerpiece and matching diamond cigar band.

THEN: Luminous in Lavender at the 2012 Screen Actors Guild Awards

‘Classic simplicity’ seemed to be the motto for Regina’s older looks. The A Cinderella Story actress looked radiant in her tiered lavender Alberta Ferretti gown as a presenter at the 2012 Screen Actors Guild Awards. With a sweetheart neckline and large asymmetrical ruffles, the color worked as a perfect contrast to King’s glistening skin. Unfortunately, her muted gold and color stone earrings and clashing costume bracelets lacked much of the personality and edge the star now consistently brings to every red carpet; there is no denying that King has now tapped into a more elevated level of style that leaves her competing with the cream of the Hollywood fashionista crop.

WOW: Dark Edge at the 2019 American Music Awards

While she may not be a recording artist herself, Regina had no problem stealing the show as presenter for Taylor Swift’s Artist of the Year trophy at the 2019 American Music Awards.  It all began with Regina’s arrival in a black sequined Ashi Studio Fall 2019 Couture gown. The dazzling garment featured an open keyhole front and off-the-shoulder straps, which flaunted her toned physique, while the shimmering fabric looked like liquid when the light bounced off of it. A beaded headpiece resembling asymmetrical bangs was only the start of her incredible accessories. The 50-year-old wore shoulder duster diamond earrings from Japanese designer Niwaka’s Umeutage collection, paired with a petal-shaped Niwaka’s Suiren diamond ring and a duo of matching diamond cigar bands from their Kuon collection. The bright bling served as the perfect contrast to the pitch black dress.

THEN: Cocktail Chic at the 2011 NAACP Image Awards

Long before she showed up at events decked out in six figures worth of diamonds, Regina kept it far more simple. The Legally Blonde 2 starlet attended the 2011 NAACP Image Awards in a sophisticated silver Enzoani cocktail dress complete with a crystal brooch shining on her hip. While the frock is still unquestionably chic, it’s a far cry from the stunning floor-length gowns she has become more accustomed to in the years since. Likewise, her pear shaped drop earrings and matching ridged cuff bracelet were a tad dull compared to the diamond sparkle we have come to expect from her more recent looks.

WOW: Hair-Raising Baubles at the 2019 LACMA Art + Film Gala Presented By Gucci

At an event where every celebrity is weaning the same designer, standing out can be a challenge. But Regina’s petal sleeve deep v-neck gown wasn’t the only part of her look to catch the eyes of fashion’s elite at the 2019 LACMA Art + Film Gala presented by Gucci. Featuring a crystal and sequin embroidered top and contrast belt with jeweled brooch detail, the Leftovers actress carried the jersey piece with style and grace. She heightened the outfit with a sky-high braided updo for her incredible purple-hued hair, a move which allowed for her Bulgari jewelry to take center stage; taking center stage, were her classic diamond Bulgari  chandelier earrings, and  not one but two of the jeweler’s iconic Serpenti diamond rings.

WOW: Multi-Million Dollar Slayage at the 2021 Golden Globe Awards

Regina kicked off the current award season with a bang! The Best Director nominee may not have won a trophy at the 78th Golden Globe Awards, but she still showed up to the virtual ceremony like she owned the place. Even over Zoom, there was no missing her sparkling Forevermark diamond drop earrings, which shimmered brightly on camera. She also sported baubles including a five-stone flower diamond ring set and eternity band. The entire look, which also included a gigantic oval diamond halo ring and sheik two-stone, was said to be valued at a massive $2,000,000.