This winter, there are a lot of fall shoe trends that will carry over their popularity. Think: practical loafers and edgy biker boots. But don't be surprised if some elevated versions of classic styles—like flats with interesting grommet detailing and tall boots with the slightest kitten heel—make their way into your closet (or Pinterest board) as well. Some spring/summer 2025 runway trends are also starting to gain some traction now. Most notably, boxing boots and peep-toe heels.
Since it's only November and the chilly season is just beginning, you might as well do a deep dive into all of our winter fashion and accessory stories, including these shoe trends. Keep scrolling for the biggest winter footwear staples that'll allow you to step into the colder temps with an immensely cool aesthetic.
Glove Shoes
An elongated upper style on shoes (also known as a glove shoe) was quite literally all over the runways. I know for a fact that my grandmother had this style in her closet—and everyone knows grandmas have the best personal style. Can I get a round of applause for cyclical fashion?
Zou Xou Glove Flat in Marfil
Mango 100% Leather Square-Toe Shoes
Kitten Heel Boots
Every year we're plagued with the task of finding the perfect winter boot. But this winter, we have the most practical solution—an ultra-low-heeled boot! Wear this style on a night out, for work, or to elevate a casual outfit. Promise, it'll be just as comfortable as a flat boot with a little more sophistication!
Staud Wally Boot Tan Suede
Silent D Erena Kitten-Heel Boots
Grommets
2010 called, and studs are back in! We can partially thank Danish brand Ganni for the grommet revival with their viral buckle ballerina flats from this past year. But you'll be seeing many different takes on the sweet yet edgy little detail this winter, and we love how many options are out there.
Zara Metal Grommet Heeled Ankle Boots
Boxing Shoes
Like a basketball shoe, only taller, basically—and a little less chunk in the sole. If you're not sure you want to dive all the way into this one, though, you can try it on for size by simply opting for high-tops.
Free People Boxing Day Lace Up Boots
Reebok x Anine Bing Freestyle Hi Shoes
Title Boxing Speed-Flex Encore Mid Boxing Shoes
Peep Toes
Yet another blast from the past that is chicer than ever. This flirty, retro footwear was all over the Miu Miu and Tory Burch SS25 runway shows, and I have to say, I think they'd make the sweetest addition to any holiday party aesthetic.
fereshte fereshte Women's High Heels Platform Sandals Ankle Strap Slingback Dress Sandal Pump Shoes Matte Black 37 - US 7
Lauren Ralph Lauren Women's Kyla Crocodile-Embossed Leather Sandals
Devin Toolen is the Fashion Assistant at Cosmopolitan where she’s responsible for anything and everything that comes through the fashion closet doors. She preps ready-to-wear, accessories, and shoes for Cosmo photoshoots and assists on set. Devin also writes fashion stories for the Cosmopolitan website. Prior to Cosmo, Devin received her BA from Villanova University and her MA from Parsons in Paris, France. While she is passionate about fashion trends and current styles, she has a deep love for fashion history, heritage and archives. Follow her fashion journey on insta: @devintoolen.
Andrea Zendejas is the Senior Accessories Editor at Cosmopolitan, where she has worked for 5+ years. Andrea handles fine and costume jewelry, shoes, and bags for all cover and fashion stories in addition to overseeing the front of book shopping pages. She also styles beauty well stories and various fashion stories for digital. Andrea previously worked at CR Fashion Book, SELF Magazine, and Women’s Health and has contributed to digital sites Harper's BAZAAR and Marie Claire. Follow her on Instagram.
