The Caribbean’s finest were dressed to impress on Hollywood’s biggest night of the year.

The 2023 Academy Awards honored the very best in cinema worldwide, but like every year, it was the fashion causing some of the most memorable aspects of the ceremonies. In a banner year that finally lauded another woman besides Halle Berry in the Best Actress category (congratulations Michelle Yeoh!), the red carpet this year was a champagne color, breaking from tradition and ushering in something new.

Trends emerged too throughout the telecast, with white seen across several stars, feathers, plunging V-necks, and sheer bodices abounded. With visual interest brimming from start to finish during the presentation, Caribbean Posh covers some of the best dressed at the Oscars representing the region.

Winnie Harlow in Armani Privé

Recognized as one of the world’s elite models, Winnie Harlow dazzled at the 95^th Academy Awards when she descended upon Ovation Hollywood in a light yellow gown from designer Armani Privé. Harlow decided to sift through the annals of fashion history with a dress created for the label’s 2005 spring couture collection. The vintage dress featured a sleeveless silhouette and curved neckline, fitted bodice, and draped train. The 28-year-old modernized the look with a black side bodice zipper and a large sequined black corsage over one shoulder strap. Another element the catwalk queen incorporated was diamonds: a set of thick diamond rings, dangling diamond earrings, and a matching necklace. To cap off the look, the Jamaican-Canadian opted for a swept updo paired with a slim black clutch to produce an elegant, understated Oscar look.

Cardi B in Robert Wun

Hailed for working with new and up-and-coming designers, Cardi B again took an unconventional approach to her latest red carpet look when she appeared at the annual Vanity Fair Oscar party wearing a stunning design from Robert Wun. In an unexpected change, the designer’s signature pleats and peplum were not front and center, but instead, the hip-hop queen was decked out in a floor-length, red ruched dress in six-inch heels. Featuring a red veil, asymmetrical bodice, and form-fitting skirt, Cardi was draped to perfection. Always one to bring her style squad to every big event, her hair was slicked down and placed into finger waves with two loops framing her face, and stylist Kollin Carter kept the red theme going across her fire engine red lipstick, cat eyes, long lashes, and custom jewelry from Azature to complete her Oscar look in peak form. But her best accessory? Her husband, the rapper Offset, posed for the cameras in a classic black tuxedo.

 

Rihanna

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The woman with arguably one of the biggest and most ambitious appearances of the night was none other than Barbados’ Rihanna, who changed outfits three times over the course of the night, and with each ensemble proving why she continues to be one of the most influential women in entertainment.

When arriving at the Dolby Theatre, Rihanna began the night in a dark chocolate brown gown by famed designer Alaïa. The futuristic look incorporated a halter crop top, black leather skirt with a detailed train with cutouts around the thighs, paired with a mesh turtleneck and strappy heels. With her hair in a bun and tendrils falling delicately to frame her face, the entrepreneur went for a bit of bling with diamond, emerald, and ruby teardrop earrings and a few baubles on her fingers. She kept the makeup natural and light with a red lip from her own Fenty Beauty collection.

For her second look of the telecast, Rihanna took to the stage to perform her nominated song ‘Lift Me Up’ from the Black Panther Wakanda Forever soundtrack in a bejeweled, sheer ensemble from fashion house Maison Margiela. The look included a black tulle embroidered top with silver beading, jacquard pants, and embellished black leather opera gloves. Designed exclusively for Rihanna by John Galliano, she completed the look in a dazzling array of diamonds from De Beers, including a set of necklaces, drop earrings, and an assortment of rings and bracelets over her gloves. With hair blown out and light eyeshadow, Rihanna gave a standout performance combined with a powerhouse aesthetic.

For her last look of the night, Rihanna took a more classic approach in a two-piece outfit from Bottega Veneta. The mint green strapless bustier was paired with a matching silk skirt, shearling stole set, and matching leather gloves. She completed the look with tresses falling to her shoulders, circular emerald-hued earrings, and custom-made Area x Sergio Rossi sandals. Her greatest accessory the past two years – boyfriend A$AP Rocky – was just as stylish in a classic black tuxedo. Paired with a cream-colored blazer and black lapels, the musician was seen several times during the night hugging Rihanna’s baby bump.

With three amazing looks in one night, Rihanna made an unforgettable impact with each outfit that had everyone talking around the world.

Naomi Campbell

Never one to be counted out of any fashion event is the supermodel of the world, Naomi Campbell, who brought the glamour as only she could for Vanity Fair’s yearly party. With a decidedly surreal take for her red carpet-presentation, the model decided on a dreamy Schiaparelli dress. The gleaming creation from their 2023 haute couture collection was designed by Daniel Roseberry and featured a high-waisted skirt coated with tiers of squared vanilla cream-hued sequins. The matching bodice was composed of two sculpted cups attached by thin straps and adorned with gold accents. To complete the look, stylist Carlos Nazario chose gold earrings, gold collar necklaces, and several rings to elevate the bling factor. She also wore a band of multicolored beaded bracelets that added another level to the ethereal ensemble.

Emerging Celebrity Style Trends and Honorable Mentions

With New York and Paris Fashion Week still a recent memory, the next stop on the worldwide fashion train was the Academy Awards, and there have been several trends that are sure to be fixtures for the upcoming seasons.

Skin Is In!

Several celebrities were spotted in sheer and nude dresses on the red carpet this year, and Janelle Monáe stood out from the pack in a sheer bodice embroidered with black beads and nude cutouts on the skirt. Not to be outdone, singer Ciara opted for a sparkling chain mail dress that she paired with opera gloves, black underwear, and black sandals – a daring look only those in peak physical condition could pull off.

The Big Sleeve

As seen on several high-profile actresses at the show, voluminous sleeves are back in a big way, thanks to a few fashion houses, notable Elie Saab, Valentino, and Tony Ward.

Return of the Roses

Flower power returned to the red carpet this year as several stars chose florals as accessories, most notably on Tessa Thompson in Moschino, Yara Shahidi in Bottega Veneta, and with Halle Berry featuring floral appliqués on a revealing white dress.

Angela Bassett Did The Thing On Red Carpet

Nominated for her second Oscar after nearly thirty years between nominations, Angela Bassett looked regal in a voluminous royal purple gown by Moschino. The stunning dress featured diagonal draping at the waist and torso, a mermaid silhouette, and a flowing train. Bassett blinged her gown out with diamond stud earrings, a matching bracelet, and a serpent necklace from Bulgari. With her tresses free-flowing past her shoulders, she completed the look with Sarah Flint shoes and a small circular sequined black bag. Win or lose, Angela owned the red carpet and our hearts!