These might shock you, but hear me out.Winter 2027 ShoesBetter Than Stilettos: By Anthropologie Slingback Wedge Heels, $178My Favorite Shoe Brand: M.Gemi The Gilda Boots, $498Like *Those* Designer Shoes: Quince Italian Leather 65mm Cap Toe Slingbacks, $94These Are a Work of Art: Jeffrey Campbell Trustee Genuine Calf Hair Pumps, $180Your shoes are probably making your outfit look dated.
Sorry, but I’ll always be that blunt friend you want to have on speed dial when you’re in an outfit bind. They dish the truth! They’re straightforward! They know the solution! Often, there’s no time for tiptoeing around the topic, especially when you’re running 20 minutes late for your very important holiday dinner. So, here’s the thing: It’s usually the little details that kind of, sort of ruin an outfit.
Bags, shoes, jewelry—when these pieces are perfect, the whole look is perfect. When they’re not, it just feels off. Given I’m the resident shoe obsessee on the team, I did a deep dive into the latest street-style looks and runway moments to create a concise guide to all the winter 2026/2027 footwear trends.
Ahead, read on for your in-the-know list of the shoes that will be huge in the next three months—and the styles that are out and, thus, making you look dated. Some of these might feel like a slap in the face, but hey, like I said, I’m honest. Happy shopping!Love these picks?
Shop our fall shoe wishlist on Picksy, then create your own wishlist to keep track of and share everything you want.Dated: Stiletto HeelsIn: Wedged HeelsI’ve never been a stiletto fan for the simple reason that they’re entirely impractical for my day-to-day life in New York City.
I think if a shoe is easy to wear in the city, it’s worth it, and the heeled style that checks all the boxes—not to mention was all over the street-style scenes I studied—is wedges. Yes, the good ol’ style of the early aughts is back, but it feels so fresh and modern for 2027. Think: structural wedges that don’t look like your granny’s shoes.
What’s more, wedges pass the subway grate test, and the fact that they distribute weight equally is so much easier on your feet.
These are a no-brainer to me.By Anthropologie Slingback Wedge Heels$178 at AnthropologieDolce Vita Hanie Wedge Boots$150 at NordstromPaige Kian Wedge Pumps$298 at NordstromFrench Connection Shia Slingback Wedge Heels$89 at NordstromDated: Boring Black BootsIn: Deep, Rich-Colored BootsOkay, listen: Black boots will always be a classic, but you can’t disagree with me that they feel a bit boring after a while.
So, styles with a similar level of versatility that feel a bit more luxe are taking their place for now: I’m talking yummy, deep colors like chocolate brown and a full-bodied burgundy (like fine wine) that you can easily style with jeans, skirts, and dresses.
It’s a small footwear shift, but trust me—it makes a huge difference when it comes to your outfit.M.Gemi The Gilda Boots$498 at Mgemi.comQuince Italian Leather Heeled Ankle Boots$150 at Quince.comDolce Vita Karlie Booties$180 at Dolcevita.comCoach Margot Boots$295 at Coach.comDated: Monochrome StylesIn: Two-Toned ShoesI’m not telling you to ditch your all-black shoes altogether; I’m simply saying there’s a reason you
should put them on pause for a minute—and that’s because two-tone styles are officially taking over.
Chanel’s iconic slingbacks probably come to mind first, but I get that we don’t all have the budget to dish out upwards of $1,000 (I certainly don’t). Luckily, plenty of brands have dropped their own versions, be it with an elegant cap-toe or a cool multicolored design, that feel more exciting than monochrome.
This season is all about subtle shifts, but these are enough to take your look from dated to in-the-know.Quince Italian Leather 65mm Cap Toe Slingbacks$94 at Quince.comScarlett Chase Anna 55 Pumps$640 at Scarlettchase.comReformation Natasha Pumps$298 at ReformationCourrèges Two-Tone Kitten Heel Embossed Toe Slingback Pumps$990 at NordstromDated: Studded ShoesIn: Zebra-Print ShoesThis might be my favorite style on the
list—and for good reason.
Zebra-print shoes are obviously eye-catching; they take a simple outfit from zero to 100 real quick, and that styling power is reason enough to invest in a few pairs. But the printed calf-hair also oozes wealth; it’s a shoe I’d expect someone living in a Park Ave. penthouse to own in multiples. And, given I’m trying to manifest that wealth in my next life (a girl can dream!), I might as well start by