50 of the Best Cute (But Comfortable) Boots Perfect for Fall/Winter Travel

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With winter coming up, I’ve been on the hunt for some non-fugly winter boots. Here I’ve rounded of 50 of the best cute (but practical and comfortable) boots to see you through the winter, wherever you’re going.

For properly practical winter wear it’s best to look at outdoors and winter specialist brands, and embrace the fact that they’re going to be a bit chunkier than summer weight footwear.

The perfect travel boot for winter keeps your feet warm and comfortable, and looks stylish teamed with jeans (ideally with tights and a dress too.) Don’t skimp on waterproofing and insulation if your climate requires it.

A few tips for winter boot shopping:

  • don’t wear cotton socks, don’t layer socks. one pair of heavyweight wool socks like these ones will keep your feet the warmest.
  • storing your rubber boots somewhere too hot and dry or with big fluctuations in temperature can cause the rubber to become brittle and crack; keep them indoors rather than the garage.
  • with insulated boots, there should be space for air to circulate around your foot; don’t go for a super tight fit
  • boots for icy climates require heavy duty (and sticky) treads; research is required.

So, let’s get cracking with the list.  I hope you find your perfect boot for winter. Enjoy!

Not quite winter where you are? Check out 50 cute but comfy flat shoes or sandals. Or I’ve got 50 perfect travel handbags for you.

TIMBERLAND CLASSICS

Kicking off this list is classic Tims – the iconic all-weather boot that never goes out of style. It’s a rugged and comfortable boot that will see you through the winter (providing you don’t live anywhere too cold and snowy). Team with chunky socks and leggings or skinny jeans. Somehow simultaneously practical and fashionable, and comes in lots of colours..

Check the latest prices and review on Amazon.

ROCKPORT COBB HILL BETHANY

The Bethany boot is a premium combat-style boot from a brand which blends beautiful vintage styles with modern ergonomics for happy feet. That means anatomical molded footbeds with arch support.  And in 8 different colours, hooray.

Check the latest prices and reviews on Amazon.

COBB HILL CAROLINE

It’s black, it’s leather, and it’s a little bit more suitable for city living than some of the boots on this list. The Caroline boot from Cobb Hill is work-appropriate but stil features seam-sealed waterproofing to see you through the fall and winter.

Check the latest prices and reviews on Amazon.

TAOS CRAVE BOOT

I love this mid-height lace-up boot from Taos. A brand who are known for their ultra comfy shoes which are great for walking. The suede collar gives it a hint of western styling. I love the brick boot which comes with a red suede collar, but the Crave boot comes in 17 different colours in total, including red and a glittery bronze.

Check the latest prices and reviews on Amazon.

TAOS RINGER BOOT

Slightly shorter than the Crave, the Ringer also has a slightly chunkier workboot feel with its metal D-rings and suede collar. Another solid boot from Taos, particularly in the versatile camel colour leather.

Check the latest prices and reviews on Amazon.

TAOS CONVOY

This cosy ankle boot from Taos has a microfibre lining plus a removable footbed for those of you who need to consider arch support. It also comes in cognac and grey, but I like the biker feel to the black version with its chunky buckle.

Check the latest prices and reviews on Amazon.

TEVA DELAVINA

This gorgeous low-slung leather boot from Teva, those purveyors of comfortable sandals, will prove a hardy companion for winter trips to milder climates. The rustic look (which comes in black and brown) looks great teamed with jeans or leggings and a dress.

Check the latest prices and reviews on Amazon.

TEVA DELAVINA SUEDE BOOTIES

I love that Teva are making practical boots in cute styles appropriate for everyday wear. The Delavina also comes in a suede bootie version with wraparound braid detail. There’s a medial zip to help get them on, a decent rubber tread and waterproofed suede to keep your feet dry.

Combined with Teva’s legendary comfort, these would be great for a winter city break or Europe trip. There’s also an option with geometric cutouts available.

Check the latest prices and reviews on Amazon.

TEVA DELAVINA DOS BOOT

Slightly higher than the previous boots, the Delavina Dos boot is a great option if you’re looking for a mid-height casual boot. It can be dressed up or down, zips on and off and is made from waterproofed leather lined with canvas. These should be comfy right out the box (be aware fit runs narrow though).

Check the latest prices and reviews on Amazon.

VIONIC LOGAN ANKLE BOOT

If you’re looking for a lightweight ankle boot that’s comfortable enough to take you around new cities but can be dressed up with ease then check out the Vionic Logan. Vionic shoes are known for their ergonomics; great orthotic arch support. No waterproofing (so suitable for dry winter climates only) but makes up for it with build quality.

Check the latest prices and reviews on Amazon.

SOREL TOFINO

Sorel are the undisputed queen of chic-but-hardcore winter boots.  And this is the classic style that they’re known for. These tough boots have a quilted upper made from a breathable waterproof canvas, topped with faux fur and lined with fleece. The footbed is molded and covered with microfleece for warmth. If cold is your enemy, these boots will be your best friend

Check the latest prices and reviews on Amazon.

SOREL TIVOLI III SNOW BOOT

With a slightly more streamlined snow boot look, the Tivoli II is made from suede and has an Ortholite footbed. Stylish and comfortable, and it comes in 7 different colours. You may wish to add additional waterproofing to the suede upper for true winter protection though.

Check the latest prices and reviews on Amazon.

SOREL JOAN OF ARCTIC

With its trademark shaggy top, the Joan of Arctic is another Sorel classic much-loved by cold weather fashionistas. Chunky lace-up D-rings and a volcanized seam-sealed rubber lower complete the look. Comes in a multitide of colours (including versions with funky neon laces or a knit top rather than faux fur)

Check the latest prices and reviews on Amazon.

SOREL CONQUEST CARLY II

It’s no surprise that this list has been dominated by Sorel so far. Here’s another great choice if you like your boots high and dry. Made from leather and canvas, he Conquest Carly II has a small chunky heel and jersey lining. I particularly like the Redwood and Umber versions which would look great with denim.

Check the latest prices and reviews on Amazon.

SOREL MAJOR CARLY

If you don’t need the full-on protection of a snow boot but still want to keep your feet warm and dry over the winter then the Sorel Major Carly has a combat/biker chic look and looks cute styled with black skinny jeans and contrasting textures. These are a super sturdy city shoe made from canvas and leather that will stand the test of time (and weather).

Check the latest prices and reviews on Amazon.

SOREL PHOENIX ZIP BOOTIES

If you want performance but don’t want to look like you’re hitting the slopes, these leather lovelies should do the trick. Cunningly disguised as normal boots, they have a seam-sealed waterproof construction and good traction on the sole, but you wouldn’t guess from the appearance.

Check the latest prices and reviews on Amazon.

SOREL EMILIE CONQUEST

These gorgeous boots are the ultimate combat boot. Same Sorel seam-sealed waterproof construction, perfect for the rainy season, teamed with a memory foam footbed and microfleece topcover.

Check the latest prices and reviews on Amazon.

SOREL WINTER CARNIVAL SNOW BOOT

Completing the line-up of Sorel icons is the mid-height Winter Carnival Snow Boot with its seam-sealed waterproof nylon upper.  These boots are warm and practical and available in some funky colour option.

Check the latest prices and reviews on Amazon.

UGG ADIRONDACK II

These hardy UGGs are another winter boot popular with folks in cold climates. A A cute and comfortable lace-up boot with sheepskin top, seam-sealed waterproof leather and suede construction, and a Vibram outsole, these with keep your feet snug.

Check the latest prices and reviews on Amazon.

UGGS ADIRONDACK

The original Adirondack is for tall-boot lovers. Same lace-up leather and suede contruction, and fold-down sheepskin top (which you can fold up to make the boot even taller). Fit does run small around the calf though, and it’s worth bearing in mind that they have a separate tongue making them less suitable for extremely cold climates.

Check the latest prices and reviews on Amazon.

UGGS ELVIA

In a similar vein you have the Elvia, which is a tall lace-up constructed from leather and textile with a wool lining. This is a further step away from the snow boots above; it’s perfect as a smart winter city boot. The styling (particularly on the chesnut colour) gives it a riding boot vibe.

Check the latest prices and reviews on Amazon.

UGGS AZARIA

These cosy UGGs keep it simple with a low leather ankle boot which is super versatile for styling with different outfits. The boots are seam-sealed and lined with shearling for warmth and comfort.

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UGG KESEY

Probably the smartest boot in the UGG winter collection, the Kesey is a stylish leather lace-up with textile panels, a buckle detail and shearling lining. These are on my Christmas list.

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UGG KILMER

UGG take on the classic workboot style with the Kilmer. Crafted from water-resistant leather and suede, the Kilmer is also lined with shearling as with other UGG boots. A great casual (but warm and practical) winter boot).

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UGG BETHANY

For something a bit different, the UGG Bethany is channelling a mid-top desert boot with its flat sole and minimalist suede design. Same great warmth and durability from UGG. Also available with canvas panels.

Check the latest prices and reviews on Amazon.

INKKAS SUEDE CAMPING BOOT

I’M IN LOVE! These might just be the sensible shoes I’ve been looking for all my life. Made in Europe from leather and Peruvian textiles, Inkkas suede boots are water resistant and super cute. Bonus – Inkkas also plant a tree for every pair you purchase. Also available in a few different colour (including black) and height variations.

Check the latest prices and reviews on Amazon.

INKKAS MUSTANG

If you don’t want to go the whole hog on winter boots, but need something a little more robust than you Chuck Taylors, check out the Inkkas Mustang. Beautiful brown conker-coloured leather with a vulcanized rubber sole (I’m not really sure what that means but it sounds coooool) and waxed cotton laces, these are perfect for a mild fall and winter.  There’s also the Cusco which is similar but replaces some of the leather with Peruvian patterned fabric.

Check the latest prices and reviews on Amazon.

BLUNDSTONE SUPER 550

Blundstone are a legendary Aussie unisex boot and fans around the world rave about their comfort and durability. With its rustic and hardy take on the Chelsea boot style, the leather Super 550 is a versatile winter boot. Look after them well and these boots will last you for years.

Check the latest prices and reviews on Amazon. 

CATERPILLAR ALEXI COMBAT

A classic design, Caterpillar are known for their hardcore workboots. The combat-style Alexi has the same styling but minus the steel toe-cap and other features you won’t need if you’re not on a construction site (or similar). They’re made of leather so will need waterproofing if you intend to be in the wet frequently. There’s a couple of different shades available (I like the Dark Snuff which is a chestnut tone).

Check the latest prices and reviews on Amazon.

UNDER ARMOUR NEWELL RIDGE HIKING BOOTS

These boots are so great if you’re in the market for a hiking boot that looks edgier and more modern than a traditional hiking boot. The GORE-TEX construction is 100% waterproof. These are lightweight (though not the warmest) and super-grippy.

Check the latest prices and reviews on Amazon.

TIMBERLAND BANFIELD MID-LACE BOOT

A classy mid-height classic leather lace-up boot from Timberland, the Banfield has a slender silhouette and looks great with jeans. Slim but sturdy, it looks though is not quite as durable as some of the winter brands listed above.

Check the latest prices and reviews on Amazon.

AHNU CHENERY

Here’s a sensible combat-styled boot from Ahnu. It’s seam-sealed to keep the water out and has a medial zip to make them easier to get on and take off (the bane of so many lace-up boots, particularly in stiff leather). Practical, versatile boots that should last you for years to come.

Check the latest prices and reviews on Amazon.

AHNU HELENA

For something a bit more glam, check out these knee-high Helena riding boots from Ahnu. Quality construction, waterproof leathers with a memory foam footbed mean these winter appropriate. Fit runs narrow though, especially in the toe box.

Check the latest prices and reviews on Amazon.

L.L. BEAN BOOT

The original duck boot with a hunting heritage, L.L. Beans are a great cross-season outdoors boot. The construction (leather and waterproof rubber) is top quality but bear in mind they have little insulation so aren’t suitable for really snowy or icy places (unless you can track down the versions lined with shearling or Thinsulate).

Check the latest prices and reviews on Amazon.

KODIAK WOMEN’S SURREY II

Retro hiking vibes with bright red laces make the Surrey II a winner. Rich seam-sealed waterproof leathers, microfibre lining and a felted wool collar, this boot is a classic that you’ll keep coming back to.

Check the latest prices and reviews on Amazon.

SPERRY TOPSIDER SALTWATER MISTY

The name is a bit of a mouthful, but these duck-style rain boots from Sperry have some features which make them a great winter boot. Check out that vulcanised rubber lower and leather upper topped with faux fur and lined with microfleece. There’s a buckle for added detail, but a medial zipper means you can get these on with ease.

Check the latest prices and reviews on Amazon.

HELLY HANSEN VANIR GALLIVANT

Fans of modern performance footwear will dig these HH boots which offer an edgy contemporary vibe (and extreme comfort). These boots will take you up mountains.

Check the latest prices and reviews on Amazon.

BOG’S SUMMIT KNIT WATERPROOF INSULATED BOOTS

I’m a biiiig fan of BOG’s boots for winter wear. Cute, comfortable, practical and warm. The Summit is a pull-on casual boot that is waterproof and insulated and looks cute with skinny jeans. Basically they’re giant socks but more useful. Or like waterproof UGGs. Plus, the whole boot is washable. BOG’S boots have a unique hole handle so you can easily pull them on over your socks and jeans.

Check the latest prices and reviews on Amazon.

BOG’S ARCATA WINTER SNOW BOOT

For wetter climates these Arcata boots have a rubber lower and laces for extra adjustment.The top part of the boot has a furry interior. They’re perfect for snowy slushy weather.  These are relatively lightweight and have good grip to stop you from sliding over in that ice. The soles are contoured with a roomy toe-box, giving you plenty of extra sock space.

Check the latest prices and reviews on Amazon.

BOG’S SIDNEY CRAVAT SNOW BOAT

One for the city slickers, these lace-up snow boots have a rubber low and fabric upper and come in a range of different colours. I love the Dr Marten vibe and high-top design which give them a stylish contemporary feel for a snow boot. Come with the customary BOG’S grip hole.

BOG’S JUNO LACE-UP TALL BOOT

The upper is a waterproof quilted nylon. There’s no tongue (to keep the boot more insulated), but the bungee cord allows you to tighten the boots up. However if you have wide calves you might want to try these on before you buy. These come in a couple of different colours including a light grey for you snow princesses out there.

Check the latest prices and reviews on Amazon.

BOG’S CRANDALL SNOW BOOT

Half way between the Summit boot and an insulated welly (galosh), the Crandall has a rubber sole to see you through wet wintery weather. The pull-on upper is neoprene lined with plush faux fur for extra toastiness. The fabric upper helps to keep them lightweight and flexible compared with heavier boots. Great for puddles.

Check the latest prices and reviews on Amazon.

MUCK ARCTIC APRES BOOT

Muck are another iconic country brand who pride themselves on their waterproofing, insulation and comfort. The Apres boot (which also comes in black) has a faux-fur trim, a rugged sole and lightweight cushioning. The height is 15 inches. Great if you’re regularly out and about in cold weather.

Check the latest prices and reviews on Amazon.

AU&MU SHORT WINTER BOOTS


These snow boots have a super-cute style and are lined with real Australian shearling. Perfect if you’re looking to stand out from the crowd in something a bit more modern. They do come in more sensible colours like black and brown, but this bright pink pair stands out for obvious reasons.

Check the latest prices and reviews on Amazon.

COLOMBIA ICE-MAIDEN II SNOW BOOT

If you’ll be spending time in snowy climates this winter, Colombia’s Ice-Maiden II could be perfect for you. This insulated technical winter boot has an advanced traction rubber sole to keep you secure on ice. I love the cute touch of the contrasting blue laces on this version.

Check the latest prices and reviews on Amazon.

COLOMBIA HEAVENLY OMNI-HEAT KNIT

For some hardcore winter cosy feels, these Columbia boots combine faux-fur, quilted textiles and a warming knit. The breathable seam-sealed membrane bootie will keep your feet dry. Like duvets for your feet.

Check the latest prices and reviews on Amazon.

PALLADIUM PAMPA CHUKKA BOOT

These are perfect if you’re somewhere milder this winter. I love the styling of these Palladium boots, which are like a cross between Chuck Taylors and a leather combat boot. The knitted cuff is a nice touch too. These are the kind of boots I live in.

Check the latest prices and reviews on Amazon.

CONVERSE WATERPROOF BOOTS

Don’t want to give up your Chucks for winter? Me neither. But it’s worth knowing that Converse do produce their iconic hi-top in a few different waterproof versions. This one is waterproofed nubuck with a vulcanized rubber sole. It should stop the wet feet at least.

Check the latest prices and reviews on Amazon.

MANITOBA MUKLUKS SNOWY OWL

If you need a warm boot for winter but just can’t stand all those laces, the Snowy Owl from Manitoba might be your perfect fit. Inspired by Aboriginal hunting shoes and featuring a Vibram sole, these boots are great for the hardcore cold (although aren’t suitable for rugged outdoors use).

Check the latest prices and reviews on Amazon.

ARIAT CONISTON COUNTRY BOOT

Another category of shoes worth investigating to keep you warm and comfortable over the colder months is the country boot. Rugged footwear from outdoors lifestyle brands (equestrian, shooting, sailing) will protect your feet from wet and wild weather. These tall lace-up boots from Ariat are made from premium waterproof leather and come lined with Thinsulate. Ok, so super-tall boots are not the most practical for travel, but I’m throwing these in here anyway because they’re quite amazing.

Check the latest prices and reviews on Amazon.

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Brown boots with text overlay '50 cute (but comfortable) boots for travel'

Image credits: Terra Evans (Unsplash), Nate Dumlao (Unsplash)

 

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