50 of The Best Boots for Winter

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Stylist Team
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Stylist has waded through this season's boots - from the finest slim-fitting flats to the wildest wedges - to bring you the best selection of winter footwear, whatever your budget.

Compiled by Charlie Anderson

  • Flat riding boots

    Tally ho! Equestrian inspired fashion is a huge trend for AW. From the high street up, there are winning interpretations of the classic riding boot to be found. The genius of this style is how utterly polished it makes any outfit.

    The longer ‘over the knee’ length riding boot long is a stronger statement, play with proportions by teaming with a voluminous cape coat.

    £220, by Somerset by Alice Temperley at John Lewis /

  • Flat Riding Boots

    This black boot goes with anything, but the real magic happens when you pair it with the new Jodphur trouser silhouette in dark gothic shades.

    £55, by Debenhams Collection /

  • Flat Riding Boots

    The influence of Downton shooting parties is clear in these colour-blocked riding boots. Wear them with heritage tweeds but choose unusual colour knits or logo jumper to keep your look modern.

    £95.00, by Monsoon /

  • Flat Riding Boots

    These beautiful conker brown boots work well with layers of autumnal shades.

    £150, by Banana Republic (020 7758 3550)

  • Flat Riding Boots

    Edgy and directional, try this clear plastic version over thick black tights with a masculine shirt dress and jacket.

    £990, by ACNE /

  • Knee High

    The leg length of winter boots has come down an inch or two this season - now it's all about the knee high. Channel the nouvelle vague look by pairing them with a wafting 70s dress, or just slip them over your fav skinny jeans.

    Get ahead of next summer’s emerging snakeskin trend with these knee high boots.

    £395, LK Bennett /

  • Knee High

    These boots are so amazing that the rest of your look can stay simple; mid blue denim, a tucked in blouse and a great jacket.

    £159.99, Mango /

  • Knee High

    These are the 70’s look entry-level boot, oxblood with a suitably chunky heel.

    £100, Topshop /

  • Knee High

    Layers of colours, block heels and a lace-up finish combine for a full-on retro boot, style them up with mixed prints and eccentric layering.

    £895, Bally /

  • Knee High

    An elegant yet strong choice and perfectunder simple winter shift dresses.

    £468, Diane Von Furstenberg /

  • Dainty Day/Night Crossover

    Take inspiration from days of old and select a boot whose dainty toe looks chic under a daytime trouser but will be a statement when paired with a dress for the evening.

    A sheer take on the Victorian boot.

    £225, Kurt Geiger (

  • Dainty Day/Night Crossover

    This sculptural wedge would look amazing with a waisted full skirted dress or suit.

    £425.00, McQ /

  • Dainty Day/Night Crossover

    To capture the orient trend perfectly wear this boot with a stream-lined silhouette.

    £845, Bionda Castana /

  • Dainty Day/Night Crossover

    This elegant boot is perfectly neutral and will work with most day to night looks.

    £482.00, SW1 /

  • Dainty Day/Night Crossover

    This feminine boot would look stunning with this winter’s strong floral trend.

    £665, Viktor & Rolf /

  • Chelsea Boots

    A boot that used to go in and out of fashion is (like Breton stripes) a seasonal standard. This bread and butter style is great with any kind of denim or even better, this season’s statement trousers.

    With a slim line sole and shiny brown hue this is an essential everyday boot.

    £85, Dune /

  • Chelsea Boots

    The elasticated ankle of this wedge boot blends into dark stocking’ed legs to give an illusion of length.

    £120 French Connection /

  • Chelsea Boots

    This boot has an earthy appeal with a wooden sole and natural leather colour.

    £69.99, Limited at New Look ( 0844 499 6690)

  • Chelsea Boots

    The rough brushed leather of these boots add another texture to an all black look.

    £195, Comptoir des cotonniers /

  • Chelsea Boots

    This boot has an elegant and streamlined evening silhouette with the brown suede toning it down - a great day to night option.

    £290, Boss Black/

  • Chunky Heeled Day Boots

    It’s time to store those spike heels for a while, this season’s heeled day boot is a chunkier affair with buckle details and coloured leather adding interest.

    Navy is once again the new black. This more rustic style will work well with a sock under a wool blanket skirt.

    £74.95, GAP /

  • Chunky Heeled Day Boots

    This boot deserves to be seen and its harder styling is perfect to set off the soft edges of the over-sized trend.

    £195, Reiss /

  • Chunky Heeled Day Boots

    A khaki parka is the perfect accompaniment to this zingy red boot.

    £225, Russell and Bromley (020 7629 6903)

  • Chunky Heeled Day Boots

    A double breasted coat would be a smart choice with this day boot.

    £70.00, Oasis /

  • Chunky Heeled Day Boots

    A lower heel makes for a more comfort driven boot but the amount of detail keep it fashion forward.

    £330.00, Tommy Hilfiger (020 3144 0900)

  • Chunky/Biker Boots

    If one was to create a model handbook then undoubtedly the Number 1 item in the uniform section would be the biker boot - alongside the listing would be guidance to wear them with skinny worn denim, knitted layers, a leather jacket and a slouchy bag.

    These are the perfect length for maximum leg flattery.

    £70, Next /

  • Chunky/Biker Boots

    The go to ‘it’ label for biker boots.

    £360, Fiorentini + Baker /

  • Chunky/Biker Boots

    Why stop at a buckle when you can add studs, and a whole heap of studs at that!

    £279.00, Ash /

  • Chunky/Biker Boots

    It’s a biker boot but it’s also a bit of a cowboy boot and it’s very fabulous.

    £213.07, Chiara Ferrangini /

  • Chunky/Biker Boots

    The more refined biker. So neat and short it would even work well with a skirt.

    £344, Marc by Marc Jacobs /

  • Natural Tan Boots

    Scotchguard at the ready! Natural tan boots with their complete colour impracticality scream luxury. Wear with cashmere. That is all.

    While these are a totally modern shape the fringing on these boots nods to the cowgirl trend.

    £155, Nine West /

  • Natural Tan Boots

    Embrace the earthy look by wearing these nubuck boots with a textured colourful knit and a fedora.

    £95, Office /

  • Natural Tan Boots

    It’s the colour that keeps this faux snakeskin cowboy boot understated, perfect with a burgundy jean.

    £380 Zadig & Voltaire /

  • Natural Tan Boots

    First seen on the catwalk at Victoria Beckham’s AW show this is a major boot for a major look.

    £1,395, Christian Louboutin /

  • Natural Tan Boots

    The sheepskin detail on these chunky day boots adds great texture and is glammed up by the gold details.

    £595, Mulberry /

  • Slim Fitting Flat Boots

    They’re a bit mod and a bit modern. The very slim fitting foot hugging boot is great with mini looks as it doesn’t cut the leg too much.

    Try the slim style in one of the season’s strongest colours - indigo.

    £40, Aldo /

  • Slim Fitting Flat Boots

    Choose these black boots with gold details then mirror the gold in the rest of your look for an

    opulent feel.

    £265, The Kooples /

  • Slim Fitting Flat Boots

    These boots can be worn with little more than a skinny jean and simple knit to scream fashion.

    £90, River Island /

  • Slim Fitting Flat Boots

    Animal print boots could be just the start of a look comprised of mixed prints and layers.

    £177.00, Sam Edelman /

  • Slim Fitting Flat Boots

    This is super mod and simple hence great with a slim black cigarette trouser.

    £230, Belle by Sigerson Morrison /

  • All Weather

    For the last few winters designers and retailers have been one step ahead of the weather game and there is now no excuse for dull ‘sensible’ wet or snowy weather boots.

    This is the crème de la crème of traditional shaped wellies. The straps add a subtle fashion edge without looking too considered.

    £99.95, Barbour /

  • All Weather

    Carry the look upwards with a winter white tonal outfit when wearing these boots.

    £135, Timberland /

  • All Weather

    This is one tough mother of a boot yet the textured panels and brass eyelets keep it looking


    £190, Sorel /

  • All Weather

    When a wellie masquerades itself as a riding boot as well as this one does it is smart enough to wear all day.

    £109, MICHAEL Michael Kors /

  • All Weather

    The natural hue of this snakeskin printed rubber boot make tone on tone dressing effortless.

    £125 Hunter /

  • Wild Wedges

    Wedge boots are fabulous - not least for their sturdy base. And if the heel is taking on a macrocosmic proportion then why not let the fashion elements dominate as well. These are strong styles to build a look around.

    Textural black and sheerling boots are perfect for a sleek tonal look.

    £1080, YSL /

  • Wild Wedges

    The proportions of these fringed wedges teamed with very slim trousers offer a striking silhouette.

    £1,100, Casadei /

  • Wild Wedges

    Wear these chunky tan boots with bare legs and a knitted jumper dress for seamless luxe.

    £330, Lacoste /

  • Wild Wedges

    Pick up on the chunky details of these wedges by teaming them with a sporty puffer.

    £79.99, Zara /

  • Wild Wedges

    Another ‘it’ boot from Isabel Marant. Create a rock & roll hippy look by wearing it with old denim, a worn t-shirt and tonnes of jewellery.

    £630, Isabel Marant / net-a-porter