When it comes to winter wardrobe staples, most of us default to the practical pieces—the warmest coat, the chunkiest knit, the boots we trust in bad weather. But lately I’ve been noticing how much impact the right-heeled shoe can have, especially at this time of year. A great heel instantly elevates simple winter outfits, making them feel intentional as well as practical. Plus, with party season literally around the corner, I've been thinking about heeled shoes more than ever before.
This season, I’ve found myself reaching for heels more often than usual—sometimes a walkable kitten heel to dress up jeans, sometimes a cute mule with a midi skirt, and sometimes a statement boot that transforms an otherwise minimal look. Heels have been the perfect reminder that winter fashion doesn’t have to be functional-only.
After spending some time scrolling through street style and the feeds of my favourite fashion people, five heeled shoe trends kept showing up. They’re wearable, they’re surprisingly versatile, and they offer fresh ways to breathe life into the winter basics I rely on year after year.
Below, I’m breaking down the winter heeled shoe trends that are worth trying this season.
5 Heeled-Shoe Trends to Try in Winter 2025:
1. Pointed Toe Slingbacks
Style Notes: Sharp, minimalist and endlessly versatile — pointed slingbacks are the classy shoe of choice this winter. They bridge the gap between day and night, pairing just as well with tailored trousers as they do with dresses.
Shop the Trend:
A classy stiletto if ever I saw one.
The styling possibilities are endless.
I think these would look cool with a pair of low-dernier tights.
These are timeless.
2. Leopard Heels
Style Notes: Leopard continues its quiet reign as fashion’s favourite print. A classic pair of printed heels or boots instantly livens up winter layers, adding a confident, playful edge to polished outfits.
Shop the Trend:
Zara's party shoes should not be overlooked.
Two trends in one.
I'm picturing these with a black midi.
The boots with the power to transform a look from drab to dazzling.
3. Chunky Toes + Ankle-Strap Heels
Style Notes: Chunky ankle-strap heels are offering a fresh alternative to delicate pumps. Their bold silhouette feels both modern and grounded—perfect for balancing out sleek 'fits.
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These also come in a fun metallic colour.
New Year's Eve shoes? Sorted.
Brown will always be my favourite shoe colour.
I'm a fan of the classic black, but these also come in gold and silver.
4. Brown Heeled Boots
Style Notes: Brown is officially rivalling black this winter. A rich-toned heeled boot feels both timeless and elevated, and works as well with chunky knit dresses as it does with straight-leg jeans.
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Wear with jeans, skirts, dresses... anything you own.
Style with your favourite jumper dress for a smart casual event.
For an elevated take on the trend, opt for suede.
So many gorgeous brown boots to choose from.
5. Embellished Heels
Style Notes: Embellished shoes are here to add a touch of sparkle to otherwise minimal looks. From studded crystals to pretty buckles, this trend (can I even call it that?!) proves that even the simplest outfit can be party-ready with the right pair of heels.
Shop the Trend:
The ultimate elegant party shoe.
No occasion is too special for these.
In a word? Obsessed.
Subtle, but pretty.
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All the Coolest Women I Follow Are Wearing This "Dated" Shoe Trend With Jeans, Dresses and SkirtsGive your pointed-toe heels a break.
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Sorry to My Heels, But I'll Be Wearing These 5 Winter Flat-Shoe Trends From Now Until Spring 2026The runways have spoken.
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Bootcut Leggings Can Look Strange With the Wrong Shoes, But These 5 Styles Look ChicNever doubt yourself again.
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Everyone Is Searching for These Expensive-Looking M&S Shoes—9 Pairs to Shop Before They’re GoneBe quick.
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Not Pointed Toes, Not Slingbacks—This Is the Partywear Shoe Trend the Chicest Dressers Will Be Styling This DecemberI'll follow their lead.
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Not Socks, Not Boots—Chic People in New York and London Can't Stop Wearing This Strange ShoeStep into the season in style.
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Alexa Chung Officially Kicked Off Party Season With the Exact LBD-Outfit Formula We're Spotting Everywhere Right NowI'm bookmarking this.
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Not Leather, Not Suede—Victoria Beckham Just Styled the Elegant Shoe Trend the Chicest People I Know Are WearingA wardrobe-altering buy.
