6 Ways to Wear Tall Boots With Different Outfits
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  • Writer's pictureBrenda

6 Ways to Wear Tall Boots With Different Outfits

Updated: Feb 13

One of my favorite types of footwear to spot during the cooler months is tall boots. I also really envy those who can easily shop for knee-high or over-the-knee boots because I unfortunately cannot. Thanks to my much-larger-than-average calves, I have a really hard time finding stylish boots that go past them.

This makes me stick to ankle boots for the most part. I would love to be able to see a pair of thigh-high boots on sale for $50 and just click order when chances are, I would need to return them.


You can therefore imagine how ecstatic I was to discover the wide calf section on DSW which offers tall boots that accommodate women with larger calves, like myself! They have hundreds of stylish boots in different colors and with different heel heights and I am super grateful to have this option available.

If you have wide calves, I suggest you check out their selection of boots that can go past your calves. I do feel like tall boots are at least a fall wardrobe staple and now I too can partake in this trend.

In today’s blog post, I would be showing you some of the best ways to style a pair of tall boots across different seasons. It is during the colder months that we tend to wear boots in general and so you would notice a focus on outfit ideas for these months.

Before we jump into the various outfit ideas I have lined up for you, I would love to share some of my favorite websites to shop for taller boots.

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

i) DSW: Of course, I had to start the list off with good old DSW. They really come through when it comes to offering a wide selection of shoes at reasonable prices. As mentioned above, they offer a dedicated section on their website of boots for women with wide calves. In addition to this, their regular section of boots boasts an impressive array of mid-calf boots and higher prices at $150 and below.

My favorite pair have got to be these Journee Collection over-the-knee boots that are made extra wide for women with big legs. They are heeled slouchy boots you could dress up or down with the burgundy one being my favorite color.

ii) Nordstrom: If your budget is a little higher, I invite you to check out the selection of tall boots on the Nordstrom site. The best option of leather knee-high boots I currently see on the site are these Elliott boots by Naturalizer.

I love the rich Fall color along with the fact that it comes in both a regular width as well as a wide one. They also have a nice chunky heel which should be easy to walk in. An easy way to style them would be with a pair of skinny jeans and a simple top. These tall Ugg boots are also highly reviewed and worth checking out.

iii) Steve Madden

Steve Madden is already a globally recognised shoes brand and I am happy to report that they also pass the tall boots test. If you’re not one to be shy of the spotlight and heel height is not a concern for you, then these thigh high boots have your name written all over them. They would look great paired with a sweater dress, mini skirt or jeans.

Now that you’ve gotten idea of wear to shop for tall boots, let’s talk about the different ways to create chic looks with them. Remember that you don’t have to wait until the winter to try some of these looks. Boots can be stylishly worn in the warmer months as well and I would be showing you how to do so.

1) Tall boots with skinny jeans

This is probably the most popular way to style tall boots. You can choose either pair of black skinny jeans or blue ones and still achieve a chic look. During the warmer months, you could opt for a pair of distressed denim and a graphic tee for a more casual look.

Skinny jeans work best here because they are the easiest jeans to tuck in and would not cause unwanted bunching. In the winter, you could pair your jeans with a chunky sweater or with a light sweater and a black leather jacket for a sleek casual look.

Image source here

2) Tall boots with sweater dresses

A sweater dress look is a great way to style tall boots during boot season. You could add a pair of black tights or leggings underneath for an extra layer of warmth or show some leg if it’s a warmer Fall Day. Knee boots or OTK boots are both great options to go with depending on your preference. Play around with sweater dresses in different colors and prints to make your outfit more interesting.

Choose a pair of heeled boots to make this a chic but warm date night look. Complete your look with a long coat and simple accessories. To fully understand why sweater dresses are such a wardrobe staple and how to wear them, check out my post on how to wear a sweater dress.

Get the look HERE

Image source here

3) Tall boots with pencil skirts

The best way to style tall boots for the office has got to be by pairing them with a midi pencil skirt. I have several blog posts on how to wear pencil skirts but this one may be the most insightful for styling a pencil skirt with boots. You can pair your midi skirt and boots with any type of sweater during the fall or winter. When it starts to warm up outside, swap your sweater for a white blouse or any other work-appropriate top.

Complete your professional look with a structured blazer to really elevate your overall look. Tall black leather boots would look especially stylish with a pencil skirt and they could be heeled or not. Just complete your look with a trench coat and you’re good to go.

Get the look HERE

4) Tall boots with mini skirts

It’s unfortunate how mini skirts can get a bad rep. They make an outfit sexier but not necessarily trashy. The rick is to balance out a sexy skirt with a more conservative top. For example, you can pair your mini skirt with a tank top and a leather jacket for a sleek and sexy look that would not be trashy.

I love the play on prints in this look.

You could also pair your mini skirt with an oversized sweater to take some attention away from your legs. Another option is to wear a pair of tights underneath to cover some leg. Try pairing a mini skirt with a cropped sweater and a pair of black riding boots for some everyday wear with a touch of sexy.

Image source here

5) Tall boots with shorts

During the summer, my favorite look to wear to an outdoor concert is a pair of shorts with tall boots and a top. You could wear this to a festival or for games night with friends. Pair It with an oversized tee, a crop top or even an old t-shirt. The taller the boot, the more attention-grabbing your look would be. Don’t forget the sunglasses and fanny pack to complete your look.

If you want it to look like you’re wearing a full pair of jeans, go for a pair of shorts that end right at the top of the boots. This would make it look like your jeans are tucked into your boots. Tall black boots work especially great to achieve this look.

Get the look HERE

6) Tall boots with oversized shirt

If you want to look like an 80’s or 90’s rockstar, this is your best option. All it takes is 2 items: an oversize shirt + a pair of over the knee boots. I love how you can build on this look to add some warmth or make this look more business casual.

You could throw on a pair of jeans underneath your shirt and you could also wear a long coat for some warmth if it’s cold outside. Instead of jeans, leggings could also be worn. Shirt dresses could also be worn in the place of an oversized shirt if you’re seeking something slightly longer.

Image source here

I hope you have gotten lots of outfit inspiration in this brief post. Regardless of our body type, we can pull off tall boot styles. You most likely already own the clothing items mentioned in this post and so I invite you to try as many as these looks as possible.

I invite you to check out my post: how to wear thigh-high boots without looking trashy.

For inspo on which shoes to wear with dresses in the winter, check out THIS POST.

Until the next post,



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