Olandria’s Vintage ‘Who What Wear’ Party Look Merged Many of Our Fave Current Trends

Reality TV sensation, model and 2026 SI Swimsuit rookie Olandria attended the Who What Wear 20th Anniversary party this week in a dazzling designer look we’ll be dreaming about for the foreseeable future.

On Thursday, Oct. 15, the star-studded event welcomed tastemakers in the fashion and beauty industries to celebrate the magazine’s special day at Hollywood’s Chateau Marmont. According to the outlet, “The party also celebrated the debut of Who What Wear’s first print issue, a special anniversary edition featuring Iris Law and Whitney Peak as cover stars.”

As noted above, the Love Island USA Season 7 breakout was among those in attendance, rocking a vintage Roberto Cavalli number from the designer’s Spring/Summer 2003 collection.

Olandria—who made her SI Swimsuit debut this year with a fashion-forward rookie shoot on Captiva Island, just off the coast of Fort Myers, Fla.—channeled several top trends in her night-out ensemble, particularly highlighting the growing focus on Y2K-inspired aesthetics. The stunning silky set featured a black, red and floral color palette, and the unique pattern on the top matched the handkerchief-style skirt’s hem for a cool, cohesive, coordinating fashion moment. Her accessories also matched the overall vibe, with the star sporting strappy black heels and a bright red handbag.

Of course, this isn’t the first time Olandria has teamed up with the beloved designer for a headline-making outfit. Most recently, the model wore a fabulously feathered ensemble to Cavalli’s Womenswear Spring/Summer 2027 show during Milan Fashion Week in late September. There, she paired the edgy ensemble with glittering jewelry and a daring, on-trend mullet hairstyle.

Speaking of “on-trend hairstyles,” Olandria’s striking early-2000s-inspired ensemble was far from the only trend the model embraced for the Who What Wear party. She also switched up her tresses for the millennial-adjacent look, rocking a dramatic bob with blunt bangs. Her makeup was equally incredible, spotlighting the model’s signature blush-centered glam: a look the star has become known for over the past few months.

And we weren’t the only ones absolutely obsessing over this gorgeous vintage moment. After a video of the model enjoying the party’s photo studio was shared on social media, many fans stopped by the Instagram comments to praise Olandria’s elegant fashion choices.

“Love this bob and Cavalli combo!!! 😍😍😍,” one user penned.

“She’s a real life doll the way she can look good in anything,” another fan quipped.

“Olandria is such an ICON. I’m obsessed with this whole look,” a commenter concluded. “Olandria in Cavalli always makes sense 😍.”

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