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Sasha Obama revives Y2K trend with toe jewelry in West L.A. sighting© Backgrid/The Grosby Group

Y2K Style

Sasha Obama brings back Y2K fashion with chic toe jewelry in L.A. outing

The former First Daughter leans into nostalgic 2000s style with flip-flops, a cropped tee, and sparkling toe rings


UPDATED JULY 31, 2025 3:20 PM EDT

Sasha Obama is embracing one of the boldest Y2K fashion trends: toe jewelry. The youngest daughter of former President Barack Obama was recently photographed arriving at a friend’s house in West Los Angeles. With her understated and bohemian signature style, her look was punctuated by glimmering toe rings that nodded to the early 2000s.

Sasha, who often sports 2000s fashion staples like chunky belts and a belly button piercing, was pictured wearing a navy maxi skirt paired with a cropped white baby T-shirt, aviator-style tortoiseshell sunglasses, a brown bag, and $26 Havaianas flip-flops.

Sasha Obama revives Y2K trend with toe jewelry in West L.A. sighting© Backgrid/The Grosby Group

She added an edge to her outfit with her jewelry selection, donning several beaded bracelets and silver accents on her feet that shone brightly against the neutral footwear.

She wore four toe rings in total: a thicker band and a small circle design on the index and middle toes of her right foot, and what appeared to be two silver bands on the middle and ring toes of her left foot.

Media Image© Backgrid/The Grosby Group
Sasha Obama revives Y2K trend with toe jewelry in West L.A. sighting© Grosby Group/BackGrid

Although toe rings have remained culturally significant in places like India, where they are often worn during wedding ceremonies, their popularity in Western fashion has faded since peaking in the late ’90s and early 2000s, a time when pop singers such as Britney Spears and Christina Aguilera and more wore one as part of their trending looks. 

Sasha and her older sister Malia, 27, were raised in the White House by Barack and Michelle Obama, and the former President has previously opened up about fatherhood and the nuances of raising daughters.

Speaking alongside Michelle on the IMO podcast, he shared, “I think we did a pretty good job of raising our girls, but I’ve said often that I think I would have had more difficulty raising a son."

Obama continued, "I think I might’ve been more judgemental, harder, and I would’ve tried to, I’d like to think I would have been more self-aware enough to combat that, but I just think father-son relationships, for me, particularly if I don’t have a dad around to show it to me, might’ve been more difficult.”

Suri Cruise also embraced Y2K aesthetic 

Sasha Obama isn’t the only famous Gen Z daughter turning heads with early-2000s-inspired fashion. Earlier this summer, Suri Noelle Cruise, the daughter of Katie Holmes and Tom Cruise was spotted several times in NYC sporting a cropped tank top that subtly revealed a belly button piercing, a style staple of the Y2K era.

Suri Cruise is spotted out and about in New York, keeping it casual in a white crop top and a patterned skirt, pairing it with sneakers, blue socks and a brown strap bag© Instar Images/The Grosby Group
Suri Cruise is spotted out and about in New York with a belly button piercing© Backgrid/The Grosby Group

While Suri has largely stays out of the spotlight, her recent public outings have drawn attention for their minimalist, vintage-inspired looks. Her pierced navel, much like Sasha’s, speaks to a larger wave of nostalgic accessorizing among Gen Z tastemakers embracing personal expression with a retro twist.

Together, Sasha and Suri represent a new generation reviving iconic elements of 2000s style, this time with an effortlessly cool, laid-back update that feels entirely of the moment.

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