7 Great Ways to Wear Midcalf Boots
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  • Writer's pictureBrenda

7 Great Ways to Wear Midcalf Boots

Updated: Feb 21

As we get ready for our second big snowstorm up here in Canada, I’m inspired to write up this blog post. When the snow starts to pile up on the sidewalks and drive ways, ankle boots tend to be a thing of the past and our taller boots get all of our attention. Who wants to be caught in 5 inches of snow with short boots?

Mid calf boots are a great in-between boot in terms of tall boots. They’re still easy enough to put on and tall enough to walk through inches of snow. This makes them a great option when you’re wondering which botts to throw on for a quick run or a day out. They can be easily styled with jeans, skirts, pants and leggings to create chic warm looks during the winter season.


In today’s blog post, I would be showing you different ways to style your mid calf boots with pieces you probably already own. These are looks you could rock in the winter or fall season, depending on your choice of layers and outerwear. I would also be sharing options of mid calf boots for women with larger calves, like myself. I know the struggle to find boots that can accommodate thick calves.

Before we dive into the world of mid calf boot outfits, I think it’s important to know where you can shop for a good pair of mid calf boots. I would be sharing some of my favorite boots at the moment in case you’re on the hunt for the perfect pair. ‘Tis the season to pull out the tall boots.

Disclosure: This post may contain affiliate links, which means that I get a commission if you decide to make a purchase through our links, at no cost to you.

Where to shop for mid calf boots

i) DSW

You’ll come to see that when it comes to my posts about shoes, DSW is a recurring name. That’s just because they offer probably the widest selection of shoes from various brands. Their price range is also very impressive with something in everyone’s budget. If you are looking for a pair of proper winter boots to trample the snow with, THESE Columbia boots are a great choice.

You could easily slip them on top of a pair of jeans to shovel the snow. They are your classic boots you could wear everyday to run errands without worrying about snow getting into your socks. The top of the boot is wide, ensuring a smoother fit for women with big calves.

ii) Nine West

Nine West is known for their elegant shoes in classic cuts and colors. When you’re off to a formal event during the winter, you want your pair of mid-calf boots to compliment your outfit. That’s where a pair of heeled mid calf boots like THIS ONE come in.

The heel height is perfect for special occasions where you want to look more glamorous without struggling to stay on your feet. Pair them with a midi or maxi skirt for an elegant look.

iii) UGG

We all know someone who must wear their Uggs everywhere, even during the summer months. This is because are known for their softness and comfort. Their mid calf boot options are also impressive and are great to create a casual look with. THESE Victoria boots might be a little taller than mid calf length but they’re close enough.

They would look great with denim jeans and an oversized sweater. To read up some more on Ugg boots + jeans outfit inspiration, check out my post: How to wear Ugg boots with jeans.

iv) Journee Collection

Remember how I mentioned earlier that I had your back if you have wide calves? Here’s the proof. Journee Collection makes it possible for those of us with wider calves to wear mid-calf boots with THESE heeled boots. You could wear them for a cocktail party with a cute dress or for date night with a shorter skirt.

v) Mia Raylyn for DSW

One of the most popular types of mid calf boots is the cowboy boot. Cowboy boots are a great way to make your mid calf look more interesting. They’re also a hit at farm weddings so don’t be in a hurry to toss them to the back of your closet once the weather starts warming up. THIS riding boot would look great paired with skinny jeans and a blazer. You could also pair it with a midi summer dress for a dressier casual outfit.

vi) Dr. Martens

Doc Martens are on the lips of all millennials and Gen Z-ers. Although most of their boots are considered ankle boots, some of them are slightly taller and close enough to the calves to be on this list. If you feel you own too many pairs of black boots, I invite you to make your shoe collection more interesting with THIS PAIR of blue Dr Martens. They would look great with a pair of black skinny jeans or cropped trousers.

vii) Mix No. 6

Not all Chelsea boots are made the same. Although your classic Chelsea boots are known to reach your ankles, they do come in different styles. Taller Chelsea boots are a great option when you’re trying to create a semi-casual outfit.

They could be paired with mom jeans or a pencil skirt to create a chic look. THESE Gamey Chelsea boots are the perfect choice for this. The best part? They cost less than $35 at the time of writing this post.

viii) Steve Madden

When it comes to creating a sexy outfit with mid calf boots, it doesn’t get better than sock boots. Just as the name suggests, the top part of the boot looks like a sock. You want this detail of your boots to show and so I suggest pairing sock booties with a mini skirt or any dress above your calves.

Steve Madden’s sock boots are some of the most popular and these REVENGE BLACK boots are a classic.

Now that you have an idea of some of the best boots when it comes to mid calf styles, let’s dive into the different outfits you can create with them. This list should serve as a guide you can refer to the next time you want to wear your favorite mid-calf boots. Feel free to remix them to better suit your personal style.

How to wear a pair of mid calf boots

1) With a mini skirt

Stand out in your mid calf boots by pairing them with a short skirt. Yes, this looks works during the winter months if you add a pair of thermal leggings underneath your skirt to keep your legs warm. Opt for a turtleneck sweater for an extra layer of warmth. Complete your look with a longline coat or a black leather jacket and you’ve got yourself a chic look.

Choose a pair of heeled boots if you’re headed for a night out with the girls. For more formal occasions, opt for a knee-length skirt.

You could pair your ankle boots with knee socks or shorter ones to create a look like THIS ONE above.

2) With a pair of skinny jeans

Probably the most popular way to style a pair of boots is with a pair of jeans. Skinny jeans work best because they’re easy to tuck into your mid calf boots. You wouldn’t have to worry about the potential bunching that occurs with wider jeans. A great way to style your jeans is with a warm sweater in a bold color.

Complete your look with a bomber jacket for a more casual look or a long coat for a dressier look. An easy look anyone could pull off would be a pair of black skinny jeans with a black knit sweater. This monochrome look is slimming and chic.

Image source here

3) With an oversized sweater

‘Tis the season for chunky knits and hot chocolate. Oversized sweaters are known to go with thigh-high boots but they can also be paired with mid calf boots. I would suggest going for a longer oversized sweater if you wish to pair yours with black leggings. This would ensure you stay warm in the cold weather. Add a pop of color to your look by choosing an oversized sweater in a fun color or bold print.

Image source here

4) With a sweater dress

Sweater dresses are a recurring clothing item in my Fall wardrobe. I’m always drawn to them when I have semi-formal events to attend during the cold months. The right sweater dress could be paired with all types of boots from knee-high boots to ankle boots. Add a pair of black tights to your sweater dress for an extra layer of warmth. Long-sleeved dresses are best for really cold days. Complete your look with a long coat and tote bag.

Get the look HERE

5) With a pair of mom jeans

I had to add mom jeans to the list because I find them the easiest to roll up for a cropped jean look. They’re also really comfortable, which is something we could all use during the cold winter days and nights. Pair your mid calf jeans with your mom jeans for a casual outfit you could wear to the store, mall, or dinner with friends. Complete your look with a cropped sweater or even a hoodie for an extra casual vibe.

Get the look HERE

6) With a pair of culottes

Culottes can be paired with mid calf boots thank to their already cropped nature. They’re also professional enough to wear to the office and so you can create chic office-appropriate looks with your boots. Choose a sweater during the Fall or winter months. Pair your culottes and boots with a blouse and blazer for a chic office look in the early Fall. Sock booties would look especially cute to create a trendy look.

Image source here

7) With a midi dress

Here’s another outfit choice you could wear to the office or for drinks after. Midi dresses are the best option to pair with mid calf boots because they’re short enough to show off your boots (unlike a maxi dress) while being long enough to wear everywhere. You don’t have to worry about dress codes in this outfit.

Image source here

For a professional setting, choose a midi dress in a neutral color. If you’re dressing up for a birthday party, try a midi dress with animal prints for a fun outfit. Throw on a pair of leather boot and a long jacket or coat

It’s ultimately up to you to decide what is the best way to style your mid calf boots. This post should give you some guidance however, especially as you most likely already own the items mentioned. Whether you’re working with biker boots, sock boots, Chelsea boots or any other style of boots, you can easily create a fashionable look with your mid calf boots.

You should check out my post: How to wear flat ankle boots with jeans for some more ideas on styling boots with jeans.

I also have a post titled: How to wear ankle boots with straight leg jeans which further demonstrates how to style boots with jeans. This time with a focus on straight-leg jeans.

Until the next post,



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