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Article: How to Style Winter Boots in 2024

How to Style Winter Boots in YEAR_TO_CHANGE

How to Style Winter Boots in 2024


Winter boots are our essential companions when the weather calls for it and snow starts to cover the streets. Their practicality, without any doubt, has stood the test of time and made them a must-have staple. Although their practical qualities are not the only ones that matter for us. Outfits with winter boots are also incredibly stylish! Thanks to the numerous fashion houses and their various boot designs, we are able to choose from an almost endless list of styles, materials, colors, shapes, etc. Ankle, knee, or thigh-high, suede, rubber, or leather, combat or duck boots — variations are unlimited. Though, to style winter outfits with boots properly, you should be aware of some general rules. We will share some fashion tips that, maybe, will help you create a unique look. Should we pair dark with dark and light with light? Should we tuck the pants inside the boots, or is it better to cuff them? Which boots suit dresses and skirts better? Can you wear rubber boots in the winter? We will answer these questions below.

We also want to show you a couple of fail-safe outfit ideas with boots to give you some inspiring insights for your future experiments. Let’s take a step into the broad world of winter footwear!

Oversize leatherette down jacket PEGGIE

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Fine-knit ribbed trousers KAREN

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Types of winter boots

To give a clear answer on how to style boots, we should consider different types of this seasonal footwear. It differs mostly by shape, length, and material. Some of them are more versatile than the others; some are more fancy and elegant. To help you pick the right pair, we suggest taking a look at these variations. These are surely not all, but they are the most common ones that you will encounter while searching for a new pair.

Ankle-high boots

These boots extend up to the ankle. They can be slim Chelseas with an insulation layer or Chukkas with a fur lining. Ankle-high boots are probably the most versatile type; they can be mixed with any garment, from jeans to dresses, and still look cool. Choose those if you value comfort and versatility, and don’t worry about the styling. These pieces will do the job as well as the rest.

Knee-high boots

These boots rise to the knee, or slightly thereunder or over. They are usually tighter around the leg shaft and the ankle than at the top, but they can also have wide ankles and folds around the leg. Consider these boots as a nice match for your dress and skirt outfits. High boots are always stylish when paired with midis or minis and short jackets or puffers.

Thigh-high boots

Also called over-the-knee, those boots extend above the knees to at least mid-thigh. They can also be as high as full-leg length. This type is sometimes considered to be erotic, but it depends on the general style of the outfit. With these ones, you should be careful if your height is below average, as they can optically shorten you.

Shearling snowboots

Shearling is a skin shorn from sheep that is tanned and then dressed in the wool left on. This type has a unique design of suede or leather on the outside and a wool clipped inside. Extremely warm boots that are usually waterproof and provide great insulation. A very warm and trendy solution for your everyday errands.

Hiking boots

Made to conquer the cold of the mountains, these boots tend to be thick enough to retain warmth and can be lined with insulation. They are usually heavier and grippier, but more supportive. For urban life, they might be a bit extreme, but if the climate is harsh enough, you should give them a try.

Rubber boots

They are usually considered rain boots but can be worn during mild wet winters as well. They are waterproof and ankle- or knee-high to keep the water away from your legs. It might not be the warmest option, but for some occasions, these work much better than common winter ones.

Duck boots

Practical and durable, these boots were designed specifically to keep your feet warm. They feature a classic boot shape with a rubber shoe sole and covering for the foot and a lace-up boot midway to the ankle or the calf. They can be easily recognized by the distinctive rubber sole. This type is a good stylish option to enhance the winter outfit in a very smart way and to stay comfortable.

Lighweight padded jacket BANKHEAD

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Denim maxi skirt HILLA

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Fundamentals of styling winter boots

When it comes to rules for styling outfits with boots, there aren’t too many, and they aren’t that strict. Although knowing some fashion tricks will allow you to create an outstanding look without any effort and will definitely help you to avoid some common missteps. So here are some basic dos and don’ts to make your styling as seamless as it is exciting. We hope that it will allow you to feel more confident and daring, and you will discover your personal fashion style to follow. Remember that these are only suggestions, and your job here is to add your unique touch to the look. 

  • Wear tall boots with a midi or a mini dress. But be careful with this outfit if your height is below average, as this particular shape can shorten the silhouette. If you are petite, try to combine ankle boots with midis and minis; they will give you more length.
  • Cuff your straight or slim-fit jeans slightly when wearing ankle-high boots. If the hem hits at the top of the boot, then you’ve matched your pieces well. Don’t go for too wide-leg trousers, as they can spoil your polished look, but also avoid the super skinny ones.
  • Don’t hesitate to experiment with trendy cropped jeans and mix them with heeled above-the-ankle boots. Be aware not to leave your skin uncovered, and try to make a long, neat silhouette. Don’t combine such a slim look with oversized tops or voluminous sweaters; go for more tailored shirts and tucked tops.
  • Try not to break your visual vertical line with contrasting colors of tops, bottoms, and shoes. Some bright combos work really well, but they have to be styled quite thoughtfully. To make it easier but keep chic and trendy, go with neutral tones with close hues to elongate the whole look.

Pinstripe blazer

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Leather chealsea boots BETHEL

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The 6 Best Winter Outfits with Boots

We’ve promised to show you some of our can’t-fail winter looks that can rock the streets, so we will. Whether you are a fashion-forward person looking for insights or you are a businesswoman who wants to simplify her styling routine, we have got you covered. So let’s have a look at how to style those boots after all.

Leather Chelsea boots with straight cropped jeans

A little bit rock-ish with a hint of vintage aesthetics, this mix is as timeless as it is trendy. Blue Straight cropped jeans RILEY paired with black Leather chealsea boots BETHEL are a classic must-have for everyday go-tos. Cropped jeans cut add a modern twist to the ensemble that can be enhanced with a relaxed sweater and a short puffer. Complete the outfit with matching bold accessories, and you are all set.

Ankle leather boots with a leather midi skirt 

To make a considered relaxed look with a street style touch, be bold and pair a button-detail leather skirt with Ankle leather boots HELIA. Duck leather boots make this combination work in an unexpected way — black leather skirt becomes less formal and more daring. An oversized sweater of light hues will perfectly complement this ensemble; you just need to throw a voluminous parka or puffer on top to hold on to the heat. Wool scarf, ribbed beanie, and let comfort follow you on the way into the cold. And don’t forget about the tights! Black tights will add a classy feeling to your look, while beige seamless ones will keep you warm without being noticed.

Suede ankle boots with knitted cashmere dress

A dress is a decent piece of clothing to become a part of a winter outfit. It might not be so obvious and require a bit more thinking and matching, but the result is usually much more impressive than a simple jeans-sweater combination. The Knitted cashmere dress from Erika Cavallini is the perfect elegant attire to be worn with warm coats and jackets. It features a slim, minimalistic silhouette and midi length that will allow you to pair it with different types of boots. Suede ankle boots TWEED is a perfect match to add some rebellious twist to the delicate dress. A long parka will complete this ensemble and will keep you toasty, while a short puffer can add more contemporary aesthetics.

Leather boots with fur lining with Gold-detail down parka

Stay warm in a Gold-detail down parka WATERSHED and mix it with a pair of Fur-lining leather boots ALTO BEAR to strike a balance in your winter outfit. Get this right, and everything else will fall into place—any in-between top and trousers will do well, as this combination is extremely versatile. Golden details on the parka ideally complement the tan cuff leather of the booties. Made to protect you from the lowest temperatures, this outfit is also water and wind resistant, which will come in handy if you are going to encounter some elements.

Roundneck bouclé sweater

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Knitted bouclé skirt

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Leather boots with fur trim with Oversize double coat

Black ankle-high fur-trim leather boots are undoubtedly a wardrobe staple as they are versatile, comfortable, and fashionable. Such items never leave the fashion trend lists due to their pragmatic and neat appearance. And as long as they are considered to be basics, they are able to match almost any garment and style. We are offering you an unexpected but trendy combination with an Oversize doublé coat from House of Dagmar. Its unusually light hue will add a fresh touch of sophisticated elegance to the outfit. Keep in-betweens simple and monochromatic to achieve even more impressive results, and complete the look with an oversized scarf and a sweet beanie hat.

Suede boots with lightweight parka

A Lightweight parka coat BELLE COTE has great protection against the cold ability, slim-fit silhouette, and a modern, fashionable design. Its versatile black hue can be successfully paired with any other color, and as an example of a good color accent, we suggest a pair of Ripple-sole suede boots ROC. Its deep brown shade will give a hint of tasteful gracefulness to the look. And as stylish as it is, this ensemble is also extremely comfortable and warm. Walks in the park can be long even during the winter if you have such attire. Outings with friends will become as pleasant as ever when the cold is not going to bother you. As an extra warm layer, you might use a wool scarf in the same color palette and a ribbed beanie. Gloves are a good idea, too, if the weather calls for it.


Our ideas are just the basics to help you start creating your unique approach to boot styling. At some point, the task might seem easy, but due to the numerous variations of footwear, the room for mistakes is also quite large. The key to success is to match shapes, colors, styles, and proportions. You don’t want your legs to look short or large, but you also don’t want your outfit to look out of trend and style.

Remember that each wardrobe needs a couple of pairs of well-made, sturdy boots for winter. Even if you are living in a mild climate, you will easily find a type of winter footwear suitable for your weather. Short or tall boots, dark or light, neat or bulky—any preferences can be satisfied with the amount of exclusive products that prominent fashion designers offer us.