I'm Wagering on It: 5 Designer Pieces Celebrities Will Sport This Holiday Season

      I experienced one of those oddly psychic fashion moments while writing this article. I was at my desk, organizing my thoughts about this story, considering who to include, and as I focused on the comeback of your beloved Tory Burch flats, Maude Apatow instantly popped into my head. It just made sense—her subtly chic, downtown-girl style is a perfect match for the shoes. I jotted it down in my notes, continued my work, and then—literally that same day—she wore them. I saw the picture, gasped out loud, and promptly messaged my coworkers. So yes, I take this little series of celebrity style predictions very seriously, and you should too. The holiday season is the ideal time for observing celebrity fashion. Everyone's out and about—attending premieres, moving between cities, going to charity galas, hosting cozy dinners in Aspen—and you can feel the overall wardrobe excitement intensifying. It’s the one time of year when even the most private celebrities are captured doing festive activities in equally festive outfits, and I can't help but speculate who will wear what next. So I compiled a list. These are the designer items I can already envision certain celebrities sporting before the year ends. Think of it as my fashion take on a holiday vision board.

      (Image credit: Getty Images) Alex has a talent for selecting cozy, high-fashion pieces and elevating them. I believe Prada’s knit bucket hat would seamlessly integrate into her relaxed wardrobe. It's understated enough to shine in street style when paired with one of her sculptural coats.

      Prada

      Mélange Knit Bucket Hat

      (Image credit: Getty Images) Who isn't excited about Kris after her extravagant 70th birthday celebration, which the police interrupted multiple times? She enjoys making a similar statement with her outfits—often selecting minimalist accessories that boldly convey “I own this space” without uttering a word. A structured Valentino newspaper boy hat seems perfectly aligned with her polished yet dramatic style (and yes, I can already envision her wearing it in Aspen).

      Valentino

      Vlogo Wool-Blend Felt Newsboy Cap

      (Image credit: Getty Images) There’s no one quite like Lori Harvey when it comes to stealth wealth glamour, and these Cartier frames were basically designed for her. The silver accents and sleek lines complement her consistently stylish travel and holiday outfits—whether she's on a yacht or enjoying brunch in L.A.

      Cartier

      Clash De Cartier 58MM Rectangular Sunglasses

      (Image credit: Backgrid) *Ahem* As previously mentioned, I predicted this one, and it materialized, so of course, I couldn't skip a dedicated section on these flats. Maude’s elegantly understated, slightly retro style makes Tory Burch ballet flats feel like a signature for her. They’re the type of shoes that subtly suggest “off-duty actress in New York.”

      Tory Burch

      Reva Travel Leather Ballet Flats

      (Image credit: Getty Images) Oprah has been spotted out and about more frequently lately, and since her wardrobe strikes a perfect balance between luxury and comfort, I immediately thought of her when I noticed these shoes. Calvin Klein’s satin mules capture that essence precisely. They're elegant enough for a holiday dinner but practical enough for her to wear while hosting a fabulous gathering at home.

      CALVIN KLEIN COLLECTION

      Kate Satin Slingback Flats

      Shop more designer items I’d love to see on my favorite celebrities:

      Aya Muse

      Tuli Wool-Blend Scarf Jacket

      The Row

      Hudson Suede Mules

      These are already quite a hit with Jennifer Lawrence.

      I'm focusing on enhancing my going-out wardrobe.

      Mackage

      Olive Down Belted Jacket

      A puffer coat that will make you feel incredibly stylish.

      This dress is straight out of a daydream.

      Tory Burch

      Reva Ballet Mule

      An adult version of the Tory Burch flats.

      Toteme

      Funnel Alpaca-Blend Neck Warmer

      I'm especially fond of scarves like this lately.

      Staud

      Liza Wool-Blend Sweater Minidress

      This dress is currently on my wish list.

      SIMKHAI

      Black River Small Suede Top Handle Bag

      As if I don't already have enough black bags, this one intrigues me.

      Polo Ralph Lauren

      Arctic Polo Bear Sweatshirt

      A cozy must-have I'm sure some celebrities will be sporting this holiday season.

      Gucci

      Alicia Interlocking G 85 Leather Mules

      I love when new Gucci channels the Tom Ford-era vibe.

      rag & bone

      Emilee Ballet Sneakers

      The ideal winter sneakers.