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How to style winter boots

A woman walks through a snowy, frosty field wearing a winter coat, winter boots and jeans.

It can be easy to feel as though style is the last consideration when you’re dressing for winter weather, with other factors like warmth, waterproofing and safety at the forefront of your mind. However, there’s no reason why you can’t be practical and fashionable when you dust off your winter boots. Below, we’ve explained how to style winter boots for both men and women.

What to wear with winter boots

The first step to styling any item of clothing is to choose your non-negotiables. These tend to be the types of clothing you only have one or two of. In this case, that might be your winter boots and thick winter coats. As you don’t have much choice in these less flexible areas, you’ll want to choose your other items of clothing to match these, rather than vice versa.

It’s also a good idea to consider warmth. Although you might automatically reach for the thick layers in winter, it’s worth thinking about what you’ll be doing when you’re out and about. If you’re going to be standing or sitting still, you’ll need plenty of insulating layers to keep you warm, but if you’re going for a hike, you’ll generate some body heat as well. Remember, it’s easier to shed a layer of clothing than it is to add one if you’ve gone out insufficiently dressed.

Finally, think about how long you’ll be spending outdoors. If you’re travelling between indoor locations, where you’ll spend most of your time without your winter coat, it’s important to consider how your outfit will look with and without your outerwear layer. A stylish scarf that matches your boots is fine, but remember that you’ll likely take it off when you go indoors.


The traditional elements of feminine style might be hard to showcase outdoors in the winter, with blouses, dresses and knitwear usually tucked away underneath a thick winter coat. However, this doesn’t mean you can’t be stylish with the items of clothing that are on display – and choosing the right trousers can be a great way to show off your winter boots.

How to wear winter boots with skinny jeans

If you’re looking to stay warm and cosy, jeans can be a good way to do it. If possible, choosing skinny or slim fit jeans is best, as this allows you to tuck the jeans into your boots easily. If your jeans are a wider leg style, opt for a pair that ends just above ankle boots, as this saves you having to tuck excess fabric in. It can also prevent the hemline of your jeans from getting snowy or muddy as they might if worn over your winter boots - cropped casual trousers are another great option for this reason.

How to wear hiking boots with leggings

For more exercise-intense winter activities, you might choose to wear leggings instead to avoid overheating on a wintry walk. Like skinny jeans, these easily tuck into any kind of boot and provide a layer of warmth close to your skin. You could also layer leggings if you need a little extra insulation, or choose a warm fabric such as wool.


For men, winter boots can be an excellent way to enjoy the great outdoors safely in the colder months. With icy and snowy conditions more common at this time of year, it’s more important than ever to wear shoes with a good grip and a thick sole. This will make it easier for you to maintain your balance and avoid slips, as well as helping to keep your feet warm.

Men’s boots tend to be chunkier than women’s, which can cause your outfit to look unbalanced if the rest of your clothes are slim fit. To remedy this, always try to pair chunky winter boots with a thick padded jacket - which is also great for keeping you warm. And don’t forget to give any leather or suede boots a coating of protective spray to keep them waterproof in rain or snow.

How to wear winter boots with jeans

As with women’s boots, jeans are a great option to wear with men’s winter boots because they’re warm, comfortable and versatile. Where possible, try to wear jeans that end just above the hem of the boot – this keeps the hemline clean and prevents the ruckling that occurs with too-long trousers. Slip on a pair of thick walking socks to keep your ankles cosy - and if you’re worried about cold air travelling up your trousers, you can always layer them with a pair of thermal leggings.

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