Hold the Ankle Boots for a Minute—Every Rich-Looking Winter Outfit I’ve Saved Features This Boot Trend Instead

There’s no doubt about it: when winter comes around there are some core pieces in our wardrobe that we all lean on. The non-negotiable, hard-working styles that become our trusted go-tos year after year. And one such item is boots.

Much like a cosy knit or a great coat, boots play an integral role in our wardrobes year-round, but especially in winter. But this season, stylish people are pressing pause on their classic ankle boots and opting for something a little different. For winter 2025, the riding boot has re-emerged. First spotted on the autumn/winter 2025 runways at Hermès and Ralph Lauren, the trend has quickly gained momentum, taking over our feeds.

Its return comes as little surprise. Countryside influences have been steadily filtering into mainstream fashion, from barn jackets and printed silk neck scarves to equestrian-inspired blazers. Riding boots strike the perfect balance between polish and practicality: endlessly versatile, they pair just as effortlessly with miniskirts as they do with leggings. Sleek and sophisticated, their flat sole ensures comfort and functionality without sacrificing style.

In a bid to incorporate a pair into my own wardrobe and see how wearable they really are, I’ve compiled five different outfits including riding boots to give you all the inspiration you need. Enjoy!

5 Chic Outfits with Riding Boots:

1. Scarf Coat + Leggings + Riding Boots

Style Notes: The most obvious way to wear riding boots is with leggings, of course. Make the whole thing look polished by adding a sleek bag and scarf jacket.

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2. Cashmere Jumper + Mini Skirt + Riding Boots

Style Notes: This is a cosy yet stylish look that can work for the weekend and the office. French-tuck your knit into a leather mini skirt, before adding tights and boots. Top tip: I always keep a pair of sparkly earrings in my bag so that if I am heading out for a drink after work, I can give my look a little lift!

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3. Blazer + Jeans + Riding Boots

Style Notes: I think tucking your jeans into your boots is such a chic way to add something a little different to a classic denim outfit. A black blazer gives this look extra polish.

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4. Silk Dress + Riding Boots

Style Notes: A silk dress, coat and boots makes for the perfect Christmas Day look, don't you think? Just don't forget your tights!

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5. Chunky Jumper + Skinny Jeans + Riding Boots

Style Notes: I don't know about you, but I think this entire outfit is giving big Princess Diana vibes. Add a tote bag and you have the perfect weekend errand-running look that will also carry you through to any evening plans too (read: the pub).

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