Sarah Michelle Gellar Revives Platform Penny Loafers in New York

Sarah Michelle Gellar pulled one of the ‘90s’ most durable shoe silhouettes back into view in New York on Monday night, pairing a short white dress and oversize black jacket with black patent platform penny loafer pumps. The silhouette nodded to a late-’90s formula that never fully disappeared: part prep staple, part oddball statement shoe, now back in rotation at full height.

Gellar wore a loafer pump that kept the upper close to the classic penny shape, with a strap across the vamp, apron stitching and a rounded square toe. The front sat on a thick platform, while a tall block heel gave the silhouette additional lift. The patent finish made the shoe read slicker and more dressed than a flat campus loafer. In one close-up, the top edge of the vamp on one shoe appeared slightly folded inward, but the rest of the shape came through clearly: glossy, chunky and squarely planted.

She styled the pair with sheer black tights, a white mini-length dress and a roomy black jacket cut long over the hips.

The timing made the reference land harder. Just days after the planned “Buffy the Vampire Slayer” revival was scrapped, Gellar walked out in a silhouette that read less red carpet polish than a wink at the late-’90s prep-meets-oddball dressing that once orbited Sunnydale, with a little Willow Rosenberg in the mix.

Both the penny loafer and the platform have been having a moment since the fall. traced chunky and heeled loafers back to the 1990s in a broader look at the decade’s returning shoe trends, and the category kept resurfacing through 2025 in flatter and higher versions alike. Amanda Seyfried wore her Miu Miu penny loafers repeatedly last fall, leaning into the silhouette’s more classic side, while Taylor Swift took the loafer idea in a taller direction with Gucci platform slingback pumps in SoHo.

Gellar has been working a platform streak of her own. In February, she wore towering gold Casadei sandals to Netflix’s “Star Search” finale in Los Angeles. While those shoes leaned overtly red carpet, her Monday night pair read more day-to-day.