How To Wear Knee High Boots: Cute Outfit Ideas in 2023 (2023)

While boot trends are constantly changing, knee high boots are a wardrobe staple that can instantly elevate any outfit. Knee high boots are classic footwear that can be versatile and chic, and women can wear these boots with everything from dresses to skinny jeans, skirts, leggings, and shorts. Whether you’re styling your boots for a night out with the girls or dressing up for a date with a formal black dress, there are many cute outfits with knee high boots to consider.

Some women will casually wear long boots with heels and jeans, while others may prefer shirt dresses with flat knee-length boots. When deciding on your style, you should think about different types of materials and colors. Black and brown knee high boots are the most popular, and often come in leather and suede. As a closet must-have that you can dress up or down, it can be a challenge knowing what to wear with your boots for a stylish ensemble.

For inspiration and outfit ideas, we’ve compiled this guide on how to wear knee high boots to create an effortlessly trendy look. From cute dresses and skirts to casual jeans and leggings, explore all the best knee high boot outfits to find fashionable styles you’ll love this fall and winter.

Knee High Boot Styles

Black Knee High Boots

Timeless and stylish, you can always wear black knee high boots and achieve that chic city look. Luckily, you don’t have to be walking down the streets of New York City in the winter to rock stylish long black boots. Whether you prefer leather or suede, black boots instantly make a fashion statement and are a must-have for your closet.

If you’re going with leather boots, choose ones with a pointed toe and skinny heel. For suede, a rounded boot and stacked heel is your best option. With pleather or patent boots, you have more variety, as they look great no matter the toe shape or heel height. Black knee high boots are extremely versatile, so you have a lot of styling choices when deciding what to wear.

For a highly fashionable and sleek look, go with an all black outfit with suede or leather boots. If you’re wanting to go for a more trendy casual style, try some knee high lace-up combat boots. Mixing white and black provides a contrast that will get you noticed, but if you want to play it safe, pair your black knee high boots with darker solid colors like gray, deep green, or burgundy.

Brown Knee High Boots

Cute and popular with so many different outfits, there’s nothing quite like a pair of brown knee high boots. While you can effortlessly wear this boot style in the fall and winter, you can still rock long brown boots in the spring and summer. In the colder months, pair knee high boots with skinny jeans and oversized knit sweaters for a casual look you can pull off going anywhere. Layer with a neutral-colored trench or plaid pea coat to complete the outfit. To make the right style choices in the warmer seasons, you’ll want to wear your boots with leggings, a chic dress, mini skirt, or some light wash cut-off jean shorts.

Tan Knee High Boots

Tan knee high boots are evidence that you don’t necessarily have to stick to the standard dark brown or black boot colors. A lighter neutral boot in a taupe, beige, or cream color is a great option as well. Long tan boots are the perfect transition piece for integrating with warmer clothing, providing a softer and more casual look that works well with spring styles. For a cute and chic outfit, you’ll want to wear lightly washed denim, wrap dresses, and silky blouses with your tan knee high boots. When in doubt, you can’t go wrong with a white shirt dress, a mini-skirt and shirt, or blue denim jeans with a sweater or button-down shirt. Choose accessories like a purse or simple gold jewelry to complement your boots.

Black Riding Boots

Black riding boots typically provide a lower heel and rounded toe. While it’s simple to pair them with equestrian-style pieces like riding pants, a white button-up blouse, or a blazer, riding boots can easily be styled with some black tights and a knit dress or with your favorite sweater and a mini skirt. For the ultimate casual outfit, try adding your black riding boots with distressed or acid wash jeans, a plain t-shirt, and a flannel shirt or chunky oversized cardigan on top. Easy to wear and simple to style, you can always pair your riding knee-high boots with leggings for a relaxed look.

Suede Knee High Boots

As a winter outfit favorite, suede knee high boots are a trendy and cozy option for the colder months, and something you definitely want to show off. Suede boots come in many different styles and colors, ranging from black to brown, grey, beige, cream, and white. Truly versatile and always fashionable, you can style suede boots to match any look.

For a casual outfit, wear this boot style with a knitted dress or denim jeans. Go for an edgy vibe by pairing your boots with a black mini skirt, a loose midi dress, or a long coat. Women can also pull off a knee-length skirt or dress in a lighter fabric, such as cotton, silk, or satin so their boots are the focus. Slouchy suede knee high boots are the epitome of comfort, but if you want a more fitted style, shop for a straight leg.

Leather Knee High Boots

While genuine leather products tend to be more on the expensive side, splurging on leather knee high boots is an investment you won’t regret. From casual get-togethers to winter weddings to holiday cocktail parties, leather boots are essential footwear to have in your closet and can be worn on many different occasions. The great thing about leather knee high boots is you don’t just have to stick to black and brown colors.

For a true statement piece, you can pick out a pair of leather boots in red, blue, white, or even a metallic color. Another bold option is going beyond the traditional calf and lambskin material and choosing a snake or alligator print instead. No matter which leather you choose, you’ll surely turn some heads with your leather boot outfits.

Flat Knee High Boots

If you’re looking for a style you can wear all year round, flat knee-high boots are perfect for all kinds of outfits. While riding boots tend to be a popular type of flat boot, you can also find knee-length versions of rain boots and lace-up combat boots for a cool look. You can style flat knee high boots with jeans, a white t-shirt and a jacket, or pull off a chic outfit with a dress or skirt. Whether you want to dress it up or down, flat boots are worth having for days you want to look fashionable but feel comfortable.

Heeled Knee High Boots

When you need dressy boots that offer some height, get knee high boots with a heel for a sexy style that will stand out. From a stiletto to a standard, block or wedge heel, high-heeled boots can take your outfit to the next level with ease. These boot styles come in leather and suede as well as a variety of prints and colors, including black, brown, tan, beige, red, blue, and grey. Depending on your desired aesthetic, you’ll want to choose different heel heights and shapes.

For something more alluring and sleek, style your formal ensemble with tall black leather boots. Perfect for first dates and classy occasions, high-heel black boots look great with midi dresses or mini skirts and chic tops. Create a smart casual look by pairing heeled brown suede boots with a maxi dress, or skinny jeans and a button-down shirt. Another comfortable and casual option is a heeled knee high cowboy boot, which works with either a pointed or rounded toe.

Knee High Boot Outfits

Knee High Boots with Jeans

As one of the most popular fashion styles, you can always wear knee high boots with jeans for a flattering look. Simple and easy to style, you can pair all types of jeans with boots and pull off a flawless finish. Generally, you’ll want to choose black or blue skinny jeans with your knee-length boots, giving you a range of options on top. Wear your brown suede boots with black jeans and a sweater to brunch, dark denim with black wedged-heel boots and a button-down shirt for a casual day out, or blue skinny jeans and a t-shirt with a jacket and tall knee highs for a chic look.

While skinny jeans and jeggings are preferred, you can also opt for a straight leg cut as long as you tuck your pants inside your boots. Avoid flare and wide-leg cuts because they can look frumpy when tucked into your boots, and will otherwise hide your fashionable footwear if worn over.

Knee High Boots with A Dress

No matter the length, pairing your knee high boots with a dress will ensure you exude femininity. There are many different types of dresses you can wear for a stunning and classy look. Most women have a favorite black dress that would be perfect with black knee high boots. You can choose leather, suede, or snake print boots and decide between a high and flat heel.

For a sexy outfit, combine your boots with a mini slip dress for a modern vibe or try a maxi or midi dress with your knee-high boots peeping out from underneath for a more sultry and timeless choice. Showing a little leg will give the illusion of height, especially when paired with a high-heeled boot. If you’re going for a more relaxed style, try a long dress with a flat heel, such as a pair of riding boots.

Knee High Boots with A Skirt

Dressing knee high boots with a skirt allows you to play with different styles and outfits. Like a mini-dress, wearing a mini skirt with high boots and a bit of leg exposed is a sexy choice that will make you look taller. During the colder months, pair your skirt with tights for warmth and comfort. Midi and maxi skirts are great transition pieces, and depending on the fabric, can easily be worn any time of year. For professional women who want a slimming silhouette, wear a pencil skirt with a blouse, sweater or button-down shirt and long boots. Feel free to experiment with different materials in your outfit, like combining a leather skirt with a cashmere sweater and some suede knee high boots. No matter your style, there is a length of skirt to fit your desired look.

Knee High Boots with Leggings

Leggings are wardrobe essentials that pair perfectly with knee high boots. While casual and comfortable, legging can still be dressed up and look fashionable when styled properly. Bundle up in the fall by combining leggings, long tunics, sweaters, oversized cardigans, scarves, and tall boots for maximum warmth and coziness. Although black leggings are popular with most outfits, you could try branching out to other solid colors like navy, cream, or grey. Make your outfit pop with a pair of brown, black or beige suede knee high boots and leggings with a thick knit sweater. You can always change it up with classic leather riding boots.

Knee High Boots with Shorts

You can rock knee high boots with shorts throughout the year for a casual look you can wear around town. Whether you’re styling leather, denim or suede shorts, your knee high boots will create a fashion-forward and chic appearance. Complement your high-waisted denim shorts with a loose lace or silk blouse and finish the ensemble with a belt. If you don’t have the right pieces to make the perfect outfit, opt for a short skirt or dress to achieve a similar aesthetic.

What To Wear with Knee High Boots

• You can wear knee high boots with jeans, dresses, leggings, skirts, and even dress pants to suit your style and the occasion.
• Black and brown boots are the most versatile and work with the widest range of outfits, but there are many colors to choose from.
• Black leather knee high boots are sleek and timeless, while long suede boots will give you texture and contrast.
• Knee high boots with heels are great for elevated styles, while flat boots offer a comfortable and casual yet stylish look.
• An all-black ensemble provides an instantly chic look and is the perfect choice for formal wear.
• Add transition pieces to your outfit so your knee high boots can easily evolve from fall and winter to spring.
• Show off your boots by being sure to wear jeans and leggings that tuck nicely into them, or easily put them on display by pairing your footwear with mini skirts and dresses.
• Have fun and experiment with different heel heights, colors, and fabrics to build your favorite looks.