Ballet Flats! Loafers! Boots! This Week's Best Celebrity Looks Showcased the Season's Best Shoe Trends

Between the new Airbnb.org Gala, the 2026 WSJ. Magazine Innovator Awards, and the Time100 Next Gala, the celebrity red carpet circuit was buzzing this week. But beyond the lights, camera, action of it all, A-listers saved their best October outfits for last—and for seasonal, street style step-and-repeats.

One thing the red carpet didn't get? Cool-girl looks from not one, but two Hadid sisters. Early in the week, Bella stayed true to her signature stovepipe jeans trend in (still available) Frame denim. She paired the '90s throwback with a fresh-from-the-box top-handle tote and leather jacket, both by Balmain.

Not long after Bella took her decadent leather duo for a spin, Gigi welcomed soft, slipper-style shoes to her ever-expanding collection of Miu Miu loafers. In New York City, the Guest In Residence founder stopped by her flagship store in her knitwear brand's best-selling Everywear Pants, Miu Miu's $8,200 Waxed Leather Jacket, and the Ruches Suede Loafers. The next day, Gigi celebrated the opening of her label's new Madison Avenue location in her go-to Kookai tank (the same halter top she wore backstage at the 2026 Victoria's Secret Fashion Show) and a plaid pencil skirt from Guest In Residence.

Now, the Hadids weren't the only stars serving enviable late fall looks this week. Katie Holmes, Rihanna, and Jennifer Lawrence followed the Hadids' lead in layered seasonal style, too. For the best celebrity fashion moments from the final week of October (and ways to recreate them in November and beyond), keep scrolling.

Gigi Hadid

Gigi Hadid started Sweatpants and Slippers Season in a surprising amount of Miu Miu, including the intentionally weathered, Waxed Suede Leather Jacket. Then, for her "groutfit," Gigi color-coordinated a light gray cardigan and Guest In Residence's Everywear Pants, a relaxed sweats-adjacent style she's worn on repeat since 2022.

As for her accessories, she sourced Miu Miu for the Pocket Top-Handle Tote and matching Ruches Loafers in chestnut suede.

Fast forward to the opening party of NYC's second Guest In Residence store, and Gigi traded the layers for her favorite (sold-out) Kookai tank top, a plaid, wrap-style skirt that she designed, and a chocolate leather biker jacket. To finish the fall look, the model carried a bucket bag with bright pink flowers and slipped on two-tone, cowboy-coded boots.

Bella Hadid

Meanwhile, in L.A., Bella went with black leather. First, she tucked a graphic tee beneath Balmain's peplum Signature Jacket, which complemented her belted, black Sphynx Bag. Embracing the '90s edge of the Balmain pieces, she sourced Frame for the low-rise, bootcut Rodeo Jeans. While Bella's beloved cowboy boots would've worked with the leather-and-denim look, she chose slingback vintage Prada pumps instead.

Katie Holmes

Katie Holmes, a Banana Republic loyalist, sampled the brand's newest designer collaboration on her NYC stroll: Banana Republic x Zankov. She stacked a striped, sold-out sweater beneath a leather jacket and traded her beloved Icon Classic Wide-Leg Jean for dark denim. She then accessorized with soft suede loafers and a Toteme top-handle bag. Fun (fashion) fact: The actor wore the same tote with another full Banana Republic 'fit in 2024.

Jennifer Lawrence

One year after Jennifer Lawrence walked the red carpet in Conner Ives's celebrity-beloved Demi Couture Robe, her off-duty winter outfit tested a different take on the duster trend. The actor chose Colleen Allen's velvety chartreuse, sidewalk-sweeping style, which matched her Miu Miu cardigan. Channeling the housecoat's retro charm, Lawrence swapped sneakers for the indoor-outdoor slipper trend in black suede. Her finishing touch? A month-old basket bag from Tory Burch's Spring 2027 collection.

Rihanna

This week, Rihanna added the most autumnal color combination to her early-winter wardrobe. Looking fresh from a pumpkin patch, the pop star zoomed from CVS to Giorgio Baldi in a cool-toned brown sweater from Phoebe Philo and olive green bottoms.

While her security carried one of her monogrammed Louis Vuitton Speedy Bags, RiRi accessorized with bug-eye sunglasses, supersized hoop earrings, and the high-vamp heels trend.

Sienna Miller

Take it from Sienna Miller: The London girl look isn't always prim and proper. While walking around London with her daughter, Marlowe, Miller made her baggy denim overalls less Americana-coded with high-vamp Phoebe Philo flats (the same sold-out slippers she wore on the red carpet this summer) and Bottega Veneta's $9,100 Small Cabat Bag. While her Polo Ralph Lauren bibs aren't available to shop anymore, Gap slashed 50 percent off a similar pair.