I'm Convinced: This Overlooked Boot Is Suddenly Cooler Than Anything Else in My Winter Wardrobe
Wondering how to wear this season's pointed-toe boots? We've rounded up six outfits so good you won't want to wear round toes this winter.
It was during one of my recent wardrobe clear-outs that I noticed the evolution in my shoe roster. Where once I would collect miscellaneous heels of varying heights, colours and finishes, I've been spending the last couple of years focusing on comfortable flats that I can run around in. The truth is, though, some styles get a bad rep and are written off as uncomfortable before we've even tried on more than one pair, and a case in point (no pun intended) is the pointed-toe boot. With their sleek silhouette and leg-lengthening appeal, pointed toe boots were the kind of '90s wardrobe staple that dressed up everything from everyday denim to more considered evening looks. But as heels began to fall out of favour after the rise of the ballet flat and loafer, so too did this sculptural style. And granted, whilst pointed-toe boots can come in all heel heights, there was something about the exaggerated silhouette that told everyone that the wearer took their outfit very seriously, something that throw-on-and-go minimalists baulked at the very thought of. That is, until now.
With fashion fully in its dressed-up era, the pointed toe brings a sharper, more confident edge to everyday dressing. Trainers, loafers, and leather slip-ons will always have their place in a well-curated wardrobe, but a pointed-toe boot draws and holds the eye rather than hiding in the background, perhaps why the fashion set is readopting the angular finish for autumn/winter 2026. Just think of the boot's versatility after all—black leather pointed-toe boots with straight-leg jeans, suede boots with relaxed leather trousers and a tailored blazer or a knee-high boot styled with a knitted midi dress? The options are endless. But if you're still not convinced that a pointed toe could work for you, keep scrolling to see six outfits that may well change your mind.
1. Leopard-Print Pointed Boots + Jeans + Faux-Fur Coat
Style Notes: In full preparation for freezing temperatures and icy winds, you'll always find a fluffy faux-fur coat in my wardrobe for bundling up against the cold. Great news then: Elsa Hosk (pictured above) has an outfit idea for making cuddly coats feel even cooler: by teaming them with easy denim and a statement animal-print boot, probably the only style strong enough to hold its own against such an eye-catching coat. Talk about taking a walk on the wild side...
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2. Suede Pointed Boots + Trench Coat + Dark Denim
Style Notes: You don't have to be subversive to show you have fashion credentials, and Anouk's classic ensemble of a thick trench, dark jeans and suede boots is a masterclass in how to style up staples. Everyone I know owns a trench coat, and for good reason. Whether you're in the office or on the go, throwing on a longline coat always looks impossibly stylish, especially when paired with a great pair of suede boots that come at an affordable price but always look expensive.
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3. Leather Pointed Boots + Leather Skirt + Colour-Pop Turtleneck
Style Notes: Looking for an outfit that really celebrates the season? See Coco's turtleneck and leather skirt. No, I don't just mean the colours (although this is a fabulous take on 50 shades of pumpkin spice); the choice of a high-neck jumper, maxi skirt and tall boots is all kinds of practical when the temperature eventually drops. It's also a good reminder that pointed-toe boots don't need to be spindly stilettos when there are plenty of tougher, more substantial heels on the market, so you don't have to worry about buying extra insoles.
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Massimo Dutti
Massimo Dutti Wool-Blend Turtleneck Knit Sweater
£50
Arma
Arma Meeka Leather Croco Skirt
£595
Anonymous Copenhagen
Anonymous Copenhagen Valle 50 Stiletto Vegetal Soft Calf Cinnamon
£325
4. Patent Pointed Ankle Boots + Trench Coat + Jeans
Style Notes: Just like Anouk, Marilyn knows the power of a good trench coat. What I love most about this outfit, though, is how she has elevated a tonal, matte outfit into something really special by swapping classic leather for a high-gloss, patent pair. If you've got a pair of boots this good, you're going to want to show them off, and whether you wear them with jeans or swap for a midi skirt or cigarette trousers, this "business on the top, party on the bottom" look is a low-maintenance, high-impact wonder.
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Burberry
Burberry Long Castleford Trench Coat in Juniper Green
£1995
With Nothing Underneath
With Nothing Underneath Crawford Jeans: Straight Leg
£150
Dear Frances
£550
5. Pointed Knee-High Boots + Jumper + Long Skirt + Leather Jacket
Style Notes: Knits are coming into their own this season, and a midi- or maxi-length tailored skirt feels like the elegant way to elevate wool, but particularly with a sleek knee-high boot. Ready to go from day to night at a moment's notice, Leia's black-and-grey look is screenshotted in my Saved folder for days cold enough to require knits and leather, but mild enough to get away with a skirt and not having to rely on tucked-in jeans.
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Whistles
Whistles Black Short Leather Trench
£499
Quince
Quince Mongolian Cashmere Crewneck Jumper
£50
Kookaï
£125
Dune London
£199
6. Pointed Logo Boots + Funnel-Neck Jacket + Shorts
Style Notes: Looking for a bolder way to make the most of boots? You've probably got a couple of weeks left to risk a bare leg à la Emili Sindlev, so lean into a maximalist boot trend so attention-grabbing that the boots could be considered the entire outfit. Logomania isn't dead; it's just rebranding, and rather than head-to-toe styling, let a tonal palette be the base that allows a standout boot to do its job. There's something delightfully noughties about this whole ensemble, and who doesn't love a little tongue-in-cheek throwback?
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