6 Heeled Shoe Trends to Wear in Winter 2025

Okay, maybe I don’t hate flat shoes—but I’ll admit I’ll choose heels over them any day. As a five-foot-tall woman, I love how a good heel—whether it’s a micro heel, kitten heel, or a stiletto—adds those extra inches and instantly makes me stand a little taller with my shoulders back and confidence up.

Over the years, I’ve curated quite a collection of heeled shoes. But as with most things in the fashion world, shoe trends come and go. This really hit me over the weekend while I was reorganizing my closet. Some of my older pairs—with rounded toes or chunky block heels—suddenly felt a little dated and less refined than they once were. So I made a donation pile, opened up the Pinterest and Instagram apps to get inspired by what’s trending now, and did a little online browsing to see what pairs caught my eye. Along the way, I noticed even more heeled-shoe trends that feel “out” for 2025—and the fresh styles worth swapping them for.

So keep scrolling to see the six heeled shoe trends to wear this winter—and six to skip—especially if, like me, you love the way a great heel can instantly elevate your outfit and your mood.

Skip: Round-Toe Kitten-Heeled Ankle Boots

Buy: Pointed-Toe Kitten-Heeled Ankle Boots

Shay wears a trench coat, black shirt, blue jeans, black belt, black kitten-heeled boots and a black khaite bag.

Disagree with me all you want, but pointed-toe boots feel more 2025 than rounded-toe ones. Additionally, they’re sleeker, as they make legs appear longer. However, don’t just pick any pointed-toe boots; choose ones with an elongated toe box, a thin kitten heel, or a uniquely curved shape, and an ankle design that hugs the foot like a sock. This style is perfect for pairing with jeans or trousers. When it comes to fabrics, there are numerous options, including croc-effect, calf-hair, suede, patent-leather, and smooth-leather.

Shop the trend:

MANGO

Faux-Croc-Leather Pointed-Toe Ankle Boots

Toteme

Slim Glossy Leather Ankle Boots

Skip: Ankle-Strap Pumps

Buy: Ballet Pumps or High-Vamp Pumps

A woman wears khaki pants with black eel high-vamp heels.

Ballet pumps and high-vamp pumps are two trendy shoe styles that are similar in that if you removed the heel, they would still look like chic flats you could wear. The ballet pump is exactly what it sounds like—a ballerina silhouette with a block heel attached. High-vamp pumps are similar in that many have a block heel, but the front of the shoe comes up a bit higher on the vamp. These shoes look adorable with dresses and skirts, but what I love is that when paired with pants or jeans, they conceal any skin showing at the top of the foot, creating a sleek, covered look similar to that of a boot, without covering your ankle.

Shop the trend:

Gap

Vegan Patent Leather Heels

AEYDE

Gabby Leather Pumps

ZARA

Low Heeled Leather Ballet Flats

Skip: Low-Vamp Pumps

Buy: V-Cut Pumps

Marilyn wears a miu miu hat, fur-trimmed leather jacket, black pants, and v-cut vamp heels.

V-cut pumps are a type of heeled shoe where the design cuts off toward the middle of the foot and extends further up the sides, forming a V shape. These shoes reveal only a small part of the skin, directing attention upward toward the ankle and shin and creating a longer visual line. They slim the foot and give the illusion of added height. This style is already part of the wardrobes of some of the fashion icons I look to the most. For example, Elsa Hosk is a fan, as is London-based content creator Marilyn, as seen here. Instead of opting for standard ballet flats or pumps, Marilyn’s choice of V-cut heeled shoes makes her outfit feel fresher and more polished.

Shop the trend:

Anthropologie

Classic Pointed-Toe Pumps

Emme Parsons

Veneto Leather Kitten-Heel Pumps

Skip: Block-Heeled Knee-High Boots

Buy: Thin-Heeled Knee-High Boots

Eliza wears a white dress, black shoulder bag, and black patent stiletto heeled boots.

Knee-high boots are a must in any fashion person’s winter wardrobe. For flat styles, riding boots and low-profile sock boots are perfect options. When it comes to heeled knee-high boots, there’s only one you should invest in this winter if you’re aiming for a polished and sophisticated look: knee-high thin-heeled boots. Thin-heeled boots, whether kitten, stiletto, or mid-height, give off a delicate yet sharp vibe that pairs well with trousers, pencil skirts, and dresses.