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The Definitive Boots Outfit Guide [Dress with Boots, Booties with Jeans & More]
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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!


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.


These are probably the most popular type of boot 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.


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!


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.

< $1,095.00 $945.00 $198.95 $995.00 $450.00 $752.00 $366.40 $395.00>

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 Tory Burch Penelope Pointy Toe or the Christian Louboutin Adox Boot.

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 is the goal.


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

< $125.30 $306.86 $212.95 $188.95 $159.95 $945.00 $945.00 $995.00 $498.00 $71.40 $373.00>


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.

< $1,395.00 $99.95 $199.95 $906.00 $332.50 $1,095.00 $93.71 $595.00 $766.00 $446.00>


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 black booties from Michael Kors or Black Manolo Blahnik pointy toe booties. Black booties are more dressy that 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 Rag & Bone brown suede booties are a great option if you want a bootie with a high heel. If you prefer a low heel then these booties from Coach are freaking cool.


When shopping for classic booties search for high-quality leather or suede material. The stitching and seams are perfect and 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!

< $569.98 $140.00 $166.95 $452.98 $395.00 $1,245.00 $945.00 $1,345.00 $595.00 $179.95 $895.00>


The mid-calf boot! These are my least favorite type of boot. 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 amoungst 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 are 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 panche 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 has some great classic styles that you can wear for years! If you want cowboy boots with lots of patterns and colors get some Lane Boots! These are fun, funky and I freakin’ love them! I want some brown boots with floral embroidery print! Yes, please!

< $328.00 $169.95 $140.00 $159.95 $474.95 $219.95 $69.95 $169.95 $104.99 $159.95 $170.00>


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 me a sexy pair of knee boots. Wearing them with super skinny blue jeans or a skirt create 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 Gillian Knee High Boot from Rebecca Minkoff 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 a 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 Gianvito Rossi knee high boots in camel suede, I die, they are so gorgeous!

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