When she's not competing on courts like the US Open's, Naomi Osaka is a fashion girl to watch. She can't help it: Even her off-season vacation style serves looks. Two weeks before Madison Square Garden's Garden Cup, where she'll take on Aryna Sabalenka, Osaka treated herself to a private tropical getaway with a suitcase full of opulent vacation outfits instead of tennis skirts.
On November 24, Osaka blessed her followers' Instagram feeds with another mid-vacation photoshoot. This time, a Jaded London backless mini dress appeared front and center. The early-2000s-inspired dress—named the Alula—began with a haltered, bubble-hem bodice and kimono-style split sleeves. Each shoulder featured a flirty cutout, teasing the entirely open back. Sequin-embellished straps connected the top to each shoulder, before delicately-draped chainlinks filled the negative space.
Naomi Osaka turned her tropical getaway into a resort-wear showdown.
The beadwork motif returned atop the thigh-grazing mini skirt, which could've been plucked straight from Mariah Carey's Y2K costume rack. Brown, bronze, and gold beads revived the beloved butterfly top of yesteryear, except along her plunging skirt's waistband. Carey wore a similar silhouette at 2000's VH1 Divas Live concert alongside low-rise jeans. According to Osaka, butterfly beadwork has emerged from its cocoon, ready to rejoin the cool-girl circuit.
Give it up for the back of the dress.
Osaka's accessories only upped the nostalgia, beginning with strappy metallic gold heels from Sienna Rossi. Faux three-dimensional flowers decorated each peep toe, while matching straps cascaded up her ankles. Blink and you'll miss the tennis star's matching anklets and toe rings, both in yellow gold.
Even her heels followed the nostalgic theme.
Osaka first arrived in the Caribbean on Nov. 5, wearing a gingham butter yellow cover-up. She's stayed loyal to of-the-moment colors and prints since then. More recently, on Nov. 17, she styled an under-$200 zebra-print dress from Delfi Collective for an after-dark dinner. Every element, from the cowl neck to the ruffled side slit, complemented current runway trends. Even Osaka's kitten heels seemed to be inspired by Spring 2026 footwear.
Another serve for the look books.
Osaka's exact location remains a mystery, but wherever she is, it certainly brings out the best fashion in her. In two weeks, she'll return to center court, well-rested, re-energized, and ready to ace another custom tennis outfit.
