Ways to Wear Boots The Definitive Guide [35+ Boots Outfits]

Do You Love Boots?

Do you love wearing ankle boots with your favorite spring outfit and over the knee boots right when it gets chilly enough to bring them out of your closet? Well, this boots style guide is for you! If you love wearing boots or want to wear boots more often but need inspiration on the different ways to wear boots throughout the year, you’re going to love this post!

In this definitive boots outfit guide, I’ll share with you the different types of boots, how to wear booties, how to wear a dress with boots, over the knee boots outfits, and of course a roundup of the must-have boots and shopping tips!

Let’s get started!

Types of Boots

Before we get into wearing different types of boots let’s first review the variety of boots you have available to buy. This section will cover the different types of boots, which styles are essentials, and what to look for in each different type of boot.

There are two ways you can approach boot shopping. Either you are looking for a pair of boots that will last you a decade and you can wear over and over again, or you’re looking for trendy boots that you might only keep for a season or two. Trendy or classic, each style comes in a variety of prices so in the following sections, you’ll see shopping options for both trendy and classic. If you’re looking for a trendy boot, it’s best to find a more affordable option, unless you have a very high shopping budget, and invest in the classic boots that you’ll wear for many years.

Ankle Boots and Booties

These are probably the most popular type of boots to wear on a daily basis. They are generally easy to pair with lots of outfits and they are my favorite type of boot.

First, let’s go over what is the difference between booties and ankle boots. Booties end right at the ankle while ankle boots can end one to four inches above the ankle. If the boots go any higher than that, they would be a mid-calf boot. It’s easy to remember, wherever the boot ends on that part of your leg is what the boot is called. Ankle, mid-calf, knee, and thigh-high or over-the-knee boots are the main types of boots.

Classic Ankle Boots

Ankle boots and booties are definitely a shoe essential! If you’re looking for a classic ankle boot opt for a brown and a black pair. For your classic brown ankle boot look for it in leather or suede. Something like the forever popular Marc Fisher Alva Boot in brown. This is a great classic option because it has a slightly pointy toe instead of a round toe, for classic boots that you’ll wear a lot always go for a pointy toe as they are more flattering. That boot has a thick stacked heel, which means you can walk a lot in them and not get as tired. And the side detailing on the boot bring some interest and dimension to it without being too much. This same boot is also available in black leather, black suede, and black embossed leather.

I’ve linked some of the best brown ankle boots I’ve found below!

Shopping for Classic Brown Ankle Boots

These boots will cost $200+ and remember they are meant to be classic and timeless. You’re paying for quality and you want to be able to wear them a lot so they do not get ruined right away which is why they will be more expensive.

For your classic black ankle boot, look for high-quality black leather without all the bells and whistles. A chic style that you could wear to an evening date, hanging out with your friends on the weekend, or even to work! When you put on these boots they need to make you feel like I’m ready to take on the day! I’m here and don’t f-with me because I’m wearing my chic black boots today! Boots like the Gianvito Rossi Pointy Toe Bootie or these Marc Fisher LTD Ulani Pointy Toe Bootie, or the Saint Laurent Kate Pointed-Toe Zip Booties.

Look for sleek black ankle boots that don’t have any crazy studs, contrasting zippers, or any accents that cause the leather to “break.” Simple clean lines are the goal.


Again these boots will cost a shiny quarter so they typically will cost $200+.

Trendy Ankle Boots

Now that we’ve gone over the two classic ankle boots let’s review the trendy styles. When looking for fun trendy ankle boots look for styles that are colorful, printed, patent, with studs, zippers, or even with sequins.

These boots are fun and bring that pop to an outfit and show your personal style. These trendy boots will be influenced by trends from the runway and are mostly seasonal. Some trendy boots do last multiple years, like the Valentino Rockstud styles, but that is not the case for most trends.

If you have money to burn on boots then go ahead and splurge on trendy designer boots but if you are on a budget I would recommend spending less than $200 on this category of ankle boots.

Here are some of my favorite trendy ankle boots that I would love to have in my shoe closet.

Shop Trendy Ankle Boots

Classic Booties

Like I mentioned booties end right at the ankle, so let’s talk about some classic booties. I love to wear booties with skinny ankle jeans or with a long flowy dress in the spring. You can also wear booties with sleek trousers and a button-down for the office.

When looking for classic booties again leather or suede in black and brown are the best options. You’ll get the most use out of them and you can even get away with wearing them year-round. There are two main types of heels I mostly see in booties. Most booties come in the skinny high heel or the low block heel.

You could go for these Christian Louboutin Leather Red-Sole Ankle Boots or Saint Laurent Kate Pointed-Toe Zip Booties. Black booties are more dressy than brown ones so keep that in mind. If you dress up often or also want booties that you can wear to events or work then invest in black ones.

If you are often dressed in casual attire and don’t dress up often then I would recommend brown casual booties as your essential. These Vince Brannen Leather Ankle Booties are a great option if you want a bootie with a high heel. If you prefer a low heel then these Acne Studios Leather Ankle Boots are pretty stylish.

Shopping for Classic Booties

When shopping for classic booties search for high-quality leather or suede material. The stitching and seams are perfect and the quality of the sole needs to be top-notch! Yes, these booties will cost over $150 but look for sales! Try to never pay full price, always look for deals! You can find designer booties for 30% to 60% off! I love finding a good deal!

Shop classic Booties

Mid-Calf Boots

The mid-calf boot! These are my least favorite type of boots. They end right at the thickest part of your calf and if not worn correctly they can make you look short, stumpy, and like you have large legs. You usually want boots or clothing to end at the slimmest parts of your body, doesn’t mean they can end elsewhere, they are just more difficult to wear, doesn’t mean you can’t.

Cowboy boots, rain boots, ugg boots, and the popular Frye Harness boot are amongst the most popular styles of mid-calf boots. From these popular mid-calf boots, I’ve only ever owned the harness boots. I do want to get a pair of cowboy boots! I do live in Austin, Texas!

If you’re going to get a rain boot, of course, go with the Hunter boots in a neutral color. Or if bright colors are part of your personal styles then get rain boots in yellow, green, or even pink.

If you want some boots for the winter and to actually keep your feet warm, then you have to get a pair of Uggs. I have never personally owned a pair of Uggs, but I didn’t buy some for my little sister. The Bailey Button Shearling boot in Brown is the most popular of the styles.

Lastly, the cowboy boots! I do love a stylish cowboy boot and I wish I could confidently pull them off but it does take an extra little panache to wear these on a weekly or even monthly basis. I live in Austin and I see so many stylish outfits with cowboy boots that I seriously can’t wait to add these to my wardrobe. Cowboy boots in brown or black of course are classic! Ariat boots have some great classic styles that you can wear for years! If you want cowboy boots with lots of patterns and colors get some Heritage Boots! These are fun, funky and I freakin’ love them! I want some brown boots with floral embroidery print! Yes, please!

Shop Mid-Calf Boots

Knee Boots

I think the higher the shaft of the boots the sexier the boots get. Now we are up to knee boots. Knee boots are a big thumbs up for me. I love a sexy pair of knee boots. Wearing them with super skinny blue jeans or a skirt creates a very stylish and sexy look. My favorite type of knee boots, you guessed it, are brown and black suede or leather boots.

A super straight and stiff shaft with minimal design and no slouching of the fabric. The sleeker the boots and the straighter the lines the better. I perfect a thicker stacked heel with knee boots instead of skinny heels. The thick heel balances the high shaft of the boot and looks balanced. These Naturalizer Kalina Boots are a great option for a classic black knee boot.

You’ll also find that with knee boots you’ll see a lot more options with a low heel, one or two inches. If you like low heel knee boots are a great option. But if you want a high heel knee boot it will take some searching. But there are some very great options. Like these Kenneth Cole Edina Knee High Boot in sleek black leather, they are so gorgeous!

Shop Knee Boots

Over the Knee and Thigh High Boots

Over the knee and thigh, high are like ankle boots and booties, the only difference is a couple of inches. I haven’t seen this definition be exact but after much research, my definition of the difference between over-the-knee boots and thigh-high boots is this: over-the-knee boots have anywhere between a 20 and 25-inch shaft while a thigh-high boot is a boot shaft over 25 inches.

You can also tell the difference between how the top of the boot ends. In thigh-high boots, the shaft gets larger towards to top so they truly go up to your thighs.

These uber-sexy boots are not for everyone so I wouldn’t classify these types of boots is essential. They are a fun style of boots that bring a whole lot of attitude to a look. If you want to add this style of boot to your boot collection then l00% black is the best option. No brown here. Black is sleek and chic. Seeing that they cover your entire leg, black is the best color for looking tall and lean. But look for a non-shiny black leather or suede. No patent boots here!

Shop Over the Knee Boots

Boots Outfits

The cute outfit possibilities with boots are endless and this will give you plenty of boot outfit inspiration throughout the year.

This is an outfit roundup of my favorite boot outfits that I’ve worn on the blog; everything from booties with jeans, over-the-knee boots outfits, brown and black boots outfits.

Depending on your style and your personal preference, a classic black or brown riding boot might just be the only boot you need. But if you’re a boot enthusiast, like I am, then you’ll want to wear flat embellished ankle boots, heeled ankle boots in black and brown, some furry boots for the snow, and black suede over-the-knee boots.

Below you’ll find over 30 boot outfits with an explanation of why each outfit works. If you want to see more photos of the outfit just click on the image or the link in the outfit title. By clicking, you’ll be directed to the original outfit post.

How to Wear Booties with Jeans

This might be one of the most researched ways to wear booties or ankle boots, with jeans! This is one of the simplest and easiest ways to wear booties. So if you’re wondering how to wear booties with jeans there are many ideas for you below!

Booties with Jeans

One of the most popular fall outfits on my blog features a pair of gorgeous and perfect brown ankle boots from Sole Society (no longer available). I wore an oversized turtleneck, matching brown blazer, belt, and distressed jeans. Overall this outfit is very cozy and can be worn on a casual date or hanging out with friends. The blazer balances the distressed jeans, so there is an outfit that has a relaxed feel but not too casual. The oversized sweater is soft and relaxed, so the blazer works to bring structure to the look.

Note that the brown booties end near the thinnest part of my leg, this creates the illusion of longer and leaner legs. You don’t want booties to cut you off any higher than a couple of inches above your ankle because they can make you appear shorter.

Also, since the turtleneck is so large in this sweater, I pulled my long hair back in a side french braid bun. It keeps the outfit look looking! If you need some braid ideas or tutorials make sure to view: 21 Braids for Long Hair with Step by Step Tutorials!

Black Jeans and Black Booties Outfit

In this boots outfit, I channeled the menswear-inspired trend and paired black ankle boots with menswear accessories, in this case, a boyfriend blazer and a men’s watch.

The blazer has a looser fit and a cute polka dot print on the inside. The feminine touch I added to this outfit was the white silk blouse, as I didn’t want this look to be entirely masculine.

Flat Brown Booties and Jeans Outfit

For a relaxed booties with jeans outfit, I wore cuffed denim jeans with flat brown boots and a matching bomber jacket. A perfect outfit for a weekend outdoors. I wore this outfit while exploring Point Lobos State Reserve in California. If you haven’t been there you need to check it out; that place is fantastic.

I expanded on the white t-shirt and jeans look by adding a brown leather jacket and brown ankle boots. Overall this is a comfortable and stylish casual outfit.

Black Jeans with Embellished Booties Outfit

Embellished boots don’t need much reinforcement when it comes to the outfit; these beauties are the center of this look. I kept the blazer, jeans, and long sleeve shirt very simple with no additional embellishments or prints. Taupe flat ankle boots paired with bright green, tan, and black make the perfect fall outfit combination.

White Jeans with Booties

I love this unexpected pairing, especially during the fall season. If I want to wear ankle boots with white jeans consider the color palette of the clothes and the color of the booties. In this outfit, I kept the color palette very light with a light gray turtleneck and matching white and gray scarf. The booties are a light brown with cute buckle detail. The only pop of color comes from the crossbody bag. If you want more white jeans outfit ideas make sure to check out: What to Wear with White Jeans: Your Ultimate Guide.

How to wear Booties with Skinny Jeans

The base of this fall outfit is very simple, black skinny jeans and a black tank top. The take this outfit from simple to cute, I first added a large Aztec printed cardigan. The larger style of the sweater brings a beautiful balance to the look because the tank top and jeans are so form-fitting. Then I wore embellished booties that have a lot going on to bring interest to the bottom half of the outfit. Lastly, a black bucket bag, bracelets, and hair in a bun completed these booties with a jeans outfit.

How to Wear a Dress with Boots

If you need some outfit inspiration on how to wear a dress with boots, below are a few ideas that you can wear throughout the year. In the outfit ideas below I included a variety of boot styles and dresses that you can pair together. From ankle boots with form-fitting or lose dresses to a sweater dress or chambray dress with mid-calf boots.

When putting together these dress and boots outfits, remember what I mentioned about balance and looking styling every day. It’s about balance and coordination. The goal is to have your boots in coordination with your outfit and achieve the style you are going for.

Ankle Boots with Dress

You can be a little more daring with your fall outfit and go bare-legged and pair your favorite black ankle boots with a form-fitting dress. This long sleeve dress and leather jacket was the perfect companion to these very cool ankle boots. The leather jacket plays on the black leather boots, and I kept the color scheme of the outfit pretty dark.

I love that these black ankle boots have a thick stacked heel and little tie accents near the top. The added accents bring personality to the ankle boots.

Casual Fall Outfit – Dress with Ankle Boots

Again, I like to have fun with my fall outfits so for this look I went a little trendy and wore a pair of flat embellished booties with a dress.

I paired this black dress with a long sweater, scarf, and coordinating gray hat. If you like the style and can get away with it, I think pairing a dress with booties is a pretty awesome combination. It’s a little contradictory but is stylish when the outfit is balanced.

Sweater Dress with Boots

Suede boots and tights go hand in hand so why not pair them with a neutral sweater dress and cozy cardigan. These slouchy suede boots have a naturally casual feel, so instead of trying to dress them up, I wore them with a sweater dress and layered a long cardigan over them. A sweater dress with boots is a great fall outfit combination.

Knee High Boots Outfits

When wearing knee-high boots the most important thing to remember when putting an outfit is that whatever you wear underneath the boots needs to be form-fitting. This means wearing skinny jeans, leggings, tights, or nothing under the knee boots. You’re looking for clean lines when wearing knee boots so you don’t want whatever bottoms you’re wearing underneath to bunch up at the top of your boots or in your boots, it looks sloppy and it’s very uncomfortable.

I love a variety of these styles of boots, from brown suede knee boots to black flat knee boots. If you’ve been trying to put together a brown boots outfit but lack ideas, there are many below. A couple of years ago I bought a pair of brown suede knee boots from Ugg that I wore a lot! You’ll see the variety of ways you can wear brown boots below!

Black Flat Knee High Boots Outfit

These boots are a combination of biker boots and flat riding boots. I like that they are a little tough-looking but stylish. I paired these boots with black skinny jeans because I wanted to create one fluid line to make me look taller and leaner. Since the bottom half is form-fitting, I was able to wear a looser sweater and top off this cute fall outfit with a gray boyfriend beanie.

Note the color coordinating in this outfit. Black, burgundy, and gray, not a lot of colors but they look great when paired together.

Knee Boots and Jeans Outfit

If you’re wondering what to wear with brown boots, then I’ve got the simplest answer for you. Pair them with dark wash jeans and add a splash of color to your outfit.

In this knee-high boots outfit example, I wore my knee-high brown boots with dark-wash skinny jeans, a brown sweater, a bright-colored scarf, and a burgundy hat. It’s always important to make your outfit interesting; this could be done with an accessory with some color or both. As you may know, I love wearing hats, so my personal touch in this outfit was the hat. This my pumpkin patch outfit for the holiday.

Leggings with Knee Boots

Like I previously mentioned, wearing form-fitting bottoms with knee or over-the-knee boots is best. In this knee boots outfit, I paired very casual brown knee boots with black leggings. I then added the slightly oversized Aztec cardigan, mustard yellow top, and olive green hat. This boots outfit would work for a fun fall weekend with friends or a casual afternoon lunch. I love the little color combination in this look and the patterned sweater adds a pretty balanced to the other solid pieces. If you need more style tips and outfit ideas with leggings make sure to read What to Wear With Leggings & 20 Style Tips on How to Wear Them.

Over the Knee Boots Outfits

Over-the-knee boots are the sexiest type of boot that you could wear, in my opinion. Like with knee boots, you either go bare-legged or wear something very form-fitting. Below I’ve shared three completely different ways to wear this type of boot. You can wear over-the-knee boots with black skinny jeans, a dress or a skirt. As you can see going bare-legged is easier to wear. Depending on the type of over-the-knee boots you get they can be a little difficult to put on at times and you definitely don’t want any cloth bunching up because that is very uncomfortable.

If you do opt to wear a dress or skirt, make sure that it’s not super short or too tight. You want to keep your outfit classy and a super short skirt and very high boots are the opposite.

Over the Knee Boots with Dress

This is one of my favorite dresses with boot pairings. The light shirt dress is a great contrast to the heavy over-the-knee boots. This outfit has an overall nice appeal because the shirtdress is more conservative and the boots are sexier. The balance between the two make for a very stylish look. Also, the vertical lines on the shirtdress create the illusion of looking taller.

To complete this over-the-knee boots outfit I added a large structured bag to keep this outfit of the dressier side.

Skinny Jeans with Over the Knee Boots

For an ultra-cool fall, look wear black over-the-knee boots with a black leather jacket and black skinny jeans. To soften up the outfit add just a tad of white or a soft fabric like a knit. I wore a white knit sweater to add contrast and balance.

Skirt with Over the Knee Boots

You can create a slightly sexy fall outfit if you combine the right pieces. I paired black suede over-the-knee boots with a black mini skirt, gray sweater, and long black coat. This outfit shows a little bit of skin, but it’s just the right amount. I didn’t pair thigh-high boots with this outfit because it just would have been too heavy with the long black coat.

Black Flat Over the Knee Boots Outfit

There is a classy way to wear over-the-knee boots and a mini skirt and it’s about staying conservative on the top half of your look and selecting the right pair of over-the-knee boots. In this over-the-knee boots outfit, I first started with the boots themselves. They are black suede boots with no heels, opting for flats boots instead of heeled boots drops the sexiness down a notch. Next, I added a thick, long sleeve, crew-neck sweater. I wanted to keep the top half completely covered. Pulled my hair back in a loose ponytail and added a forest green hat. By keeping these details in mind, I created a balanced and classy look while it is a little sexy. Do you love hats as much as I do? Check out, 40+ Outfits with Hats: How to Wear a Hat with Style & Ease!.

Sweater Dress with Over the Knee Boots

For this boots outfit, I kept the same style tips in mind as the previous outfit. How can I pair a mini dress with boots and not look inappropriate? Under the large sweater dress, I added a turtleneck in the same color palette. I was going for a monochromatic outfit. I then added a black leather belt to accentuate my waist because the sweater is very loose-fitting without it. The finishing touches were a gray hat and a black structured handbag. I love this outfit example of how you can pair a sweater dress with boots.

Wow! I know, that was a lot! I hope this post has inspired you to wear boots in a variety of ways throughout the year! I hope I have answered your question on how to wear boots with jeans, how to wear a dress with boots and the different ways to wear boots.

If you have any questions, please leave them in the comments below! Remember to pin your favorite outfits!

Stay Stylish,

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