Heeled Boots in Winter? Only if You’re Brave!

Key Points

  • Wear heeled boots for certain occasions during the winter months.

  • Take extra precautions when wearing boots with heels to stay safe on ice and snow.

  • Certain factors will influence your choice of heeled winter boots.

Picture this: It's December and you've been invited to a holiday party. You've got the cutest new dress to wear and really want to pair your favorite heeled boots with it. But the forecast is calling for snow and you're thinking about ditching the whole outfit in favor of pants.

There are many different kinds of boots on the market, and they all have different purposes. You buy snow boots for the cold winter days and winter boots for errands and everyday wear. But how do you wear heeled boots in the winter?

Boots with heels are fashionable and functional. There are many occasions to wear boots of this nature. Before you decide how to wear them, consider when you might wear them.

When To Wear Heeled Boots

Face it: Boots with heels are not the most practical winter-weather footwear. Like any pair of boots, they have their purposes. You don't want to wear them to sled or shovel, but there are good reasons to wear heeled boots in winter.


When invited to a winter wedding, it's often hard to figure out what to wear. You need warmer fabrics, more layers, and the right colors. Footwear is also important to consider. You don't want anything with an open toe. Heeled boots are a good fit for a winter wedding. They have style and class, but keep your feet warm and cozy from the car to the venue and back.

Heeled boots on steps


Depending on the dress code at your office, heeled boots may be a great idea for work. Wear them with a dress or pantsuit to give your outfit some extra style and keep your feet warm all at once. Keep a few pairs in classic colors like brown and black, and you have boots for any work attire.


You want your feet to remain warm and protected on a date with your spouse or a prospective suitor, but you don't want to wear snow boots to accomplish that task. Instead, boots with heels help you dress up while remaining practical about the temperature outside.

A Night Out With Friends

You may enjoy dressing up for a night on the town with your friends. Whether going to a bar, singing karaoke, or having dinner, dressing up and showing off your style when your friends gather is fun. Heeled boots keep you warm and looking good while you trek from place to place.


It is not as practical as wearing winter boots, but high-heeled boots keep your feet warm and dry if you need to run errands between meetings. Beware of the slick spots and get those errands done looking fly.


You want your feet to be comfortable as you honor someone's life, but you need to look nice and dress respectfully at the same time. Heeled boots fit the bill. You dress elegantly and stylishly, but your feet are warm when you travel to the cemetery for the burial portion of the service.

What To Wear With Heeled Boots

If you have boots with heels, what goes with them? High-heeled boots are popular and stylish. Thankfully, there are many outfits they complement.


Pair high-heeled boots with a dress and wear the get-up to a wedding, work, or other formal occasions. If you have a long dress, ankle boots with heels keep you warm and elegant. Wearing a shorter dress, like knee or calf length, calls for taller boots. Find heeled boots that raise to the mid-calf or even to the knee. Your legs remain warm and the heels look great with the dress.

Shirts and Skirts

Like a dress, heeled boots also work well with skirts. Pair the right colors with each outfit, and wear the boots to dress things up further. Keep skirt length in mind, as you would with a dress, and choose boots that help you avoid too much leg exposure in the cold weather.

Jeans and Sweaters

Dress up even a casual look with heeled boots. Wear the outfit on a date, a ladies' night out, or casual office gatherings. The boots fit in with many options and elevate the outfit from casual to dressy for the right occasions.

Heeled boots with jeans and bag

Different Heel Styles

Heeled boots, like high-heeled shoes, have different kinds of heels available. Choose based on appearance, comfort level, and safety. Any boot with heels is more of a danger in the winter weather; keep that in mind as you look at heel options.


Wedge heels are safer than other options as they offer height without putting balance into question. Wedge boots have a block of material throughout the bottom of the shoe. Your whole foot is higher off the ground than usual, but the heel is higher than the rest of your foot. Since your whole foot elevates from the ground, you have a balance advantage.


When you think of high heels, this is likely what comes to mind. This heel on a boot is thin and precarious in the snow. Your toes are close to the ground, and your arches rise so your heel elevates above the rest of your foot. Balancing is hard — especially in the snow and ice. Boots with stiletto heels are stylish and attractive but are dangerous.

Heeled stiletto boots


Get the look of a heel without as much danger when you choose block-heeled boots. Boots like cowboy boots often have a block heel. The heel is higher than the soles and arches, but it's a block of material and easier to balance in wintertime.


Platform boots are similar to wedges because there's material on both the shoe's front and back sides. The difference is that the wedges contain a complete block of material, while platform boots have a space between the shoe's front and the higher-heeled portion. This heeled boot is safer than a shorter heel, but wearers still turn their ankles with a wrong move.

Staying Safe in Heeled Boots

As you look outside and notice the snow and ice, recognize that heeled boots are not the safest or warmest option. You're a smart cookie. But you also want to be a cute cookie.

There's a time and a place to wear heeled boots. Keep yourself safe when doing so; these tips help you stay upright and stylish each time.

Park Close

If you have heeled boots on, it's no time to park as far away as possible in the parking lot like you might on a nicer day. Instead, park close, or have the driver drop you at the door if you're sharing a ride. You don't want to have to walk over any more snow or ice than necessary. Heeled boots keep your feet warm, but they're a hazard when it comes to slipping, sliding, and falling.

Walk Slowly

You may need to reach your destination by a certain time, but that's no reason to rush when walking in heeled boots. It's a better idea to walk slowly and carefully so you stay upright. If you rush and fall because of your speed, you are even later to your event! Taking careful steps makes all of the difference.

Watch for Ice

Ice glimmers in the sun, and you might not catch yourself before you step on it. Winter doesn't always have sunlight, so watch for ice that doesn't show. Try to avoid stepping on patches of snow that look hard. They hide ice beneath the fluffy parts of the snow. Step on it slowly and carefully if you cannot avoid the ice.

Avoid Snow

Heeled boots are not snow boots. They're stylish and elegant, but they're not supposed to protect you from the dangers of walking through the snow. Boots featuring heels slide easier, so avoid walking through the snow whenever possible. Wear these boots when the sidewalks are clear, and you do not have to worry about encountering as much snow.

Time The Occasion

You only want to wear heeled boots if the occasion calls for it. If you're sledding with your kids, snow boots are the right choice. Wear heeled boots for warmth, but at times when you're going to hang inside more than out. Heeled boots have their occasions; timing their wear keeps you safe.

Practice Keeps You Safe

No one is born knowing how to walk. Likewise, no one is born knowing how to walk in high heels. Practice walking in your heeled boots around your house so you're confident about how they operate. You don't want to turn an ankle when you walk in them outside. The more you wear them, the easier it is to walk cautiously but confidently.

Change Inside

There's nothing wrong with wearing snow boots from your car to the door. Put your heeled boots in a bag and switch them out when you're safely inside. Snow boots help you to get through the snow and ice safely, and the heeled boots look great upon arrival.


Heeled black calf boots

Finding the Best Heeled Boots

Feet are like fingerprints: No two are exactly alike — not even your own! What works for your feet does not work for someone else.

You need to find heeled boots that look good, suit your needs, and fit comfortably. Podiatrist Dr. Suzanne Levine, DPM admits that heels are not always good for feet, but there are occasions to partake: “It’s like having your cake but not making it a daily activity. It doesn’t have to be done every day or in excess, but there is nothing wrong with wearing a fabulous pair of heels!”

The key to your success is finding the right pair and wearing them on the proper occasions.

Start With Style

The ultimate reason to wear heeled boots is style. You want boots with a particular color, material, and look. When you look for snow boots, functionality is the most crucial aspect. With heeled boots, style is more important. Find styles you know flatter you and go from there.

Get The Proper Fit

You know your foot size, but not every shoe or boot has the same design. Before you assume your size and get boots that don’t fit well, try them on! Bring the socks you want to wear with them. You might wear thicker socks in the winter, and trying boots on with thin socks throws off the sizing. You might get boots half a size larger than usual to accommodate comfortable, insulating socks for warmth.

Choose Heels for Comfort

What kind of heels are you comfortable in? That is a huge question you must answer as you look at boot options. If you feel it's impossible to walk in them, don't get stiletto boots. Do they look great? Sure. Are they right for you? Not necessarily. Try on boots with different heels and walk around. If you have to walk slower than normal or feel your ankle turning every other step, you need different heel options.

Remember Versatility

Boots are an investment, and you may not be able to afford a different pair to fit every outfit you have. Instead, get versatile boots. Choose colors that go with many items in your wardrobe.

Black and brown are the most popular colors because they go with most outfits. If you have boots that look good with jeans but also help you to dress up with a skirt, you may wear them more often.

Have a Budget in Mind

Heeled boots are stylish and popular, and a wide variety of brands and prices are available. Before you fall in love with boots that are way out of your price range, set a budget and look at options only within that range. If you find boots that are too expensive for you, save up for them or get options that cost less so you don't regret your choice when you can't cover other bills.

Heeled knee length boots

Check Insulation

Since boots cover your feet and perhaps ride up your leg, they create more warmth than shoes. However, some boots are warmer than others. Heeled boots are not generally practical, but some have insulating qualities that help maintain heat and avoid moisture within the interior.

Insulation levels measure in grams starting around 100g and rising from there. If the heeled boots have insulation, they help keep you warm whenever you wear them. Heels of any kind are not practical for winter wear, but with insulation, you know they aid you in staying warm.

Consider Materials With Care

Even if you plan to sparingly wear heeled boots, they'll be out during the winter months, so consider their materials.

Suede boots, for example, don't stand up well against water. Winter has a lot of melting snow, puddles, and other things that damage boots of this kind. Fabric boots are okay with water, but they get dirty and stained.

Think about how you plan to wear the boots, how you need to care for them, and what mishaps could occur with certain materials.

Heel Height

Boots with heels come in a variety of heights. You might get boots that make you an inch taller than usual. Some boots give you five inches of height. Consider your comfort level, the style you want in the boots, and what you're comfortable with in heel height. Many folks start by wearing shorter heels and work up as they gain comfort through wearing boots.

Save Your Winter Style With Heeled Boots

You may get bored with your winter attire. You wear sweatpants, sweaters, jeans, and snow boots. You need to keep warm, and layering up is an intelligent way to go. But your style doesn't have to suffer because it's cold outside.

Instead, invest in a pair of heeled boots to dress yourself up for certain occasions. The boots are still practical, in some ways, because they offer warmth and coverage to your feet and parts of your leg. Be careful about when and where you wear them as they are also often a danger in the winter.

Putting on heeled black boots

If you have experience with heels, you'll be comfortable wearing heeled boots. Purchasing stiletto heels without a second thought is straightforward. If you don't have experience walking in heels, start with a platform or block heel until you get used to the different heights. Your safety is essential — especially in the winter months.

It's not uncommon for people to have multiple pairs of boots in their closets. Have a pair of snow boots for shoveling and sledding, winter boots for errands and everyday use, and heeled boots for work, weddings, and other elegant occasions. Take good care of any of these boot options and use them for years.

For more up-to-date info on the latest boot trends, styles, and purchasing options, subscribe to BootAuthority.

Was this article helpful?