Katie Holmes's Boat Shoes Add a Preppy Twist to Fall's Silk Skirt Trend

My silk skirts didn't get much street time last fall. This year, Katie Holmes is making sure I won't make the same mistake again, one dose of inspiration at a time.

Around lunchtime on September 4, Holmes soaked up the New York sunshine outside L'Artusi, an Italian hotspot in the West Village. She was photographed, to-go bag in hand, wearing the end-of-summer silk trend. (It's already been co-signed by Zoë Kravitz and Jennifer Lawrence, my favorite A-list New Yorkers.) Zoom in and you'll see her brown knee-length midi featured white polka-dots. Until now, I wasn't sure if summer's most popular pattern would stick around this fall. But,with Holmes's endorsement, it's certainly not going anywhere.

Always on board for an unexpected color combo, the Dawson's Creek star paired the slip with a sporty white-and-yellow long-sleeve.

Seeing Holmes in anything but ballet flats is a rare occurrence—like spotting a Hermès Birkin-less Jennifer Lopez. This time, she swapped her signature footwear for brown penny loafers. Instead of the structured styles in Dakota Johnson, Meghan Markle, and Gigi Hadid's closets, her leather flats mimicked boat shoes. Each elongated toe box featured a monochrome bow, as most maritime silhouettes do.

Holmes was in on the silk trend as early as Nov. 2024, when mine started hibernating for the winter. Before performing in Our Town on Broadway, she styled a slinky maxi skirt with a cashmere sweater from Falconeri. Both pieces were burgundy, one of fall 2024's most sought-after shades. She accessorized with a Tod's top-handle bag. Velvet Mary Janes, courtesy of Aeyde, made her polished separates feel ultra-festive.

September is just getting started, and already, Holmes's daily rotation has taken an autumnal turn. At this rate, she'll be wearing faux fur and plaid outerwear (style director Sara Holzman's favorite fall staples) before Halloween.

Shop Fall Styles Inspired by Katie Holmes