How to Look Stylish in Your Winter Boots

How to Look Stylish in Your Winter Boots

You have to love winter boots. They can keep you warm and looking great at the same time. For many of us, however, they can be just a bit tricky to style. With all of the different options for boot height, style, and function, how do you look stylish in your winter boots? Here are a few tips.

Keep the Casualness or Formality Consistent

Some boots are so casual they practically ask to be paired with your favorite women’s jeans and a casual top. Others would look out of place with that comfy denim and would work better with a nice tweed skirt and a women’s white blouse. You can spot the level of formality of a pair of boots in several ways.

Most Western-style boots are more casual. Although you can probably dress them up with a casual skirt and sweater, any topstitching or fringe promotes a casual look. Completely smooth leather (like women’s riding boots) is a bit more formal, although they can be dressed up or down. Most high-heeled boots or boots made from patent leather are on the formal end of the continuum. You might be able to wear them with jeans, but you would want a more tailored-looking blouse or a fun dress to go with them.

Keep the Silhouette Even

Chunky-looking boots (anything from hiking boots to chunky booties to cowboy boots) typically look good with heavier-looking fabrics and women’s sweaters . By pairing chunkier boots with chunkier clothing, the silhouette will remain even looking. Likewise, more delicate-looking boots would pair well with light- to medium-weight fabrics and a more delicate silhouette.


Booties are one of the most flexible kinds of boots. With the boot shank at or just above the ankle, they look great under jeans or casual pants or with tights and a long skirt and sweater. Booties will give you instant insulation against cold weather while still being easy to wear both indoors and out. Booties are also great for commuting or running errands in snowy or icy weather. If you know you will be out in the elements, make sure to choose a pair with a non-slip sole and a low heel. A classic Chelsea bootie is always a nice choice.

Knee-High Boots

Every woman needs a pair of knee-high boots. You can wear them with knee-length or longer skirts with a blouse or sweater, pair them with your favorite jeans tucked in, or even wear them under casual pants for extra insulation on a frosty day.

When shopping for knee-high boots, keep both the height and width of the boot in mind. Typically, the shank should come up to about an inch below the knee. The calf of the boot should be comfortable—neither too tight nor so loose that you feel like you are floating around in them. Just like with the clothing in your wardrobe, your footwear including knee-high boots should fit you. A well-made, properly fitted pair of boots can last for years. If you are shopping in a brick-and-mortar store, ask for assistance if you need it. If you are shopping online, measure before you buy (sometimes calf diameter is included in the descriptions of boots for instance) as well as make sure that the return policy is generous in case you need to return them.

Over-the-Knee Boots

Over-the-knee boots are becoming increasingly popular, and you don’t have to end up looking like a pirate while wearing them. Simplicity is key with over-the-knee boots. They are dramatic all by themselves, so you don’t need a lot more to make a great outfit. They look great with shorter dresses and women’s skirts if you want to show off those gams. The hem should be at least as high as the top of the boot itself, perhaps a bit higher.

Proper fit is also key with over-the-knee boots. In addition to the proper size of the footbed, you also need boots that fit through the calf and up over the knee while allowing you to move comfortably. Many over-the-knee boots have zippers that run the length of the boot to help with this. Make sure to try them on and practice walking (or dancing!) in them before you buy. This is one of the advantages of shopping online.

Snow Boots

Winter snow boots are necessary for everything from winter sports to running errands to commuting to work in the snow. When choosing snow boots, consider how and when you will be wearing them. Are they just for shoveling snow or making snowmen or will they be more transitional footwear taking you through your commute and into your working day? Choose the level of casualness, waterproofing, and color to match your anticipated activities. You will probably feel more comfortable commuting in neutral-colored boots. If they are just for play, choose any fun color that you like. Form should follow function on this one.

Whether you’re going out to play in the snow, going out to a show, or just running errands around town, the right boots can make your outfit both comfy and stylish.


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