Katie Holmes Joins Kylie Jenner at the Forefront of the Round-Toe Shoe Trend's Redemption Arc
The time has finally come.
I'm just going to ask the question we're all thinking: Are round-toe shoes back?
The Millennial-coded fashion trend hasn't been seen en masse since 2012, but that doesn't mean it's been dormant. For months, the shoe style has been stealthy plotting to overthrow the pointed-toe kitten heels and slingbacks that have dominated fashion in the 2020s—whether we like it or not.
Round-toe shoes first quietly appeared on the Alaïa runway before Kylie Jenner swapped her sharper heels for a pair. It appears other brands have taken note and now, fashion is in the midst of a large-scale siege.
Kylie Jenner wore an archival Alaïa dress with round-toe pumps in January 2025.
Tod's has likewise been instrumental in the round-toe redemption arc. The luxury brand is famed for their quiet luxury-style sophistication and exorbitant price tags—two features they're now applying to fashion's resurgent shoe shape.
The label sent several circular styles down the runway during their Womenswear Fall/Winter 2025/2026 at Milan Fashion Week last February. Months later, said styles are beginning to hit celebrity wardrobes, like that of actor Katie Holmes.
On Tuesday, May 20, Holmes attended a star-studded evening at Tod's Madison Avenue storefront. She was outfitted in the brand's freshest styles, wearing a drop-waist leather dress that hasn't even hit stores yet. Her accessories were also Tod's creations, with the star sporting their T Timeless Shopping Bag and a pair of round-toe pumps. Made from Napa Leather, the espresso-colored pair costs $1,175 at retail.
Katie Holmes stepped out in a pair of her own at a May 20 event at the Tod's boutique.
Between these celebrity supporters and the relaunch of Tory Burch's Reva Flats (the patron saint of round-toe shoes), it won't be long until this trend returns to the top of the mainstream again.
Shop Round-Toe Shoes Inspired By Katie Holmes and Kylie Jenner
