Casual Boots

Casual Boots Ideas

How to Wear Knee High Boots

Fall and winter are the perfect time for knee high boots. I find myself reaching for them time and time again, which is probably why I have several pairs. I wear them with jeans, dress pants, leggings, skirts, and even dresses. If you’re wondering how to wear knee high boots continue reading because I’ll cover knee-high boots styles, outfit ideas and style tips.

First, let’s take a look at the typical styles of knee-high boots, and then I’ll go over how to wear knee boots, offering up some stylish knee high boots outfits for inspiration.


Knee high boots have a taller silhouette making you look long and lean and offering several cold-weather advantages over booties or even ankle boots. Because they come up higher on the leg, they tend to keep you warmer, and they’re much better at keeping rain, sleet, and snow from getting inside your boots (making for wet and uncomfortable feet).

what to wear with knee high boots - Love these outfit ideas and style tips on how to wear knee high boots

Classic Knee High Boots

The majority of the knee-high boots you find today are simple and classic; smooth leather or suede that reaches from toe to knee. They can have buckles or straps, are typically zippered, and come in a variety of colors, from your standard black and brown to tan, green, burgundy, and navy. Perfect for everyday wear with jeans, leggings, trousers, and skirts.

how to wear knee high boots- Love these outfit ideas and style tips on how to wear knee high boots

Riding Knee High Boots

This is a classic boot, fashioned after English riding boots. They come up to the knee, with a rounded top edge. They have a heel, usually 1-inch or less in height, which was used to prevent the foot from sliding out of a stirrup. Typically found in black or brown, and often two-tone, like the ones you see here. They may have buckles or straps and are usually zippered. Sleek and stylish, riding knee high boots can be worn anytime, and pair well with jeans and leggings.

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Motorcycle Knee High Boots

Motorcycle-style knee high boots are heavier overall, with a thicker sole, are either zippered or laced and usually adorned with buckles. This is a casual boot and, while stylish, is not appropriate for the office. Pair with jeans or leggings.

how to wear knee high boots with skirts - Love these outfit ideas and style tips on how to wear knee high boots

Dressy Knee High Boots

Dress boots are those with some height, be it from a standard heel, stiletto, chunky heel, or wedge. They come in leather, suede and synthetic materials, with or without embellishments. Dress boots, despite their name, can be worn with just about anything, from jeans, leggings, and trousers to skirts and dresses.

While there certainly are other styles of boots out there, most are not appropriate for everyday wear. Snow boots, Uggs, and moccasins are three examples. These more casual styles, while comfortable, are for more specific occasions, like snow adventures, wearing indoors, or for a more boho casual look.

How to wear knee high boots

You probably have one or more of the above knee high boot styles in your closet. Maybe they just sit in your closet, or you only wear them with jeans. The purpose of this post is to get those boots to see the light of day more often and help you style knee high boots outfits. So let’s get to it.


Jeans are the quintessential pairing with boots. Worn tucked in or out, they can be worn with classic, riding, motorcycle or dress boots, depending on the look you are going for.

Pair those blue jeans with a pair of black motorcycle boots, tee, and moto jacket on the weekends, black skinny jeans with black boots and an oversized sweater for a comfy brunch look, or dark wash denim with dressy wedged boots and button-down for Friday casual at work.

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I’ve even worn white denim jeans with tan boots, which I find to be a better pairing than the darker black or brown boot. The options are limitless here. Whether it’s colored denim or classic blue jeans, boot-cut or skinny, you can pair them up with boots for a perfectly stylish fall or winter ensemble.

outfits with knee high boots - Love these outfit ideas and style tips on how to wear knee high boots

Leggings are also the perfect complement to boots, as they are naturally tight fitting and slip easily into any style of boot. Top them off with a long tunic and scarf, grab your boots and you’re out the door for a lunch date in no time. I like to bundle up in a warm sweater, leggings, and boots or pair them with a long-sleeve tee, oversized cardigan, and boots when heading to the weekend farmer’s market or into the city for a shopping trip with my friends.

For work, you can pair your trousers with a classic, riding or dress pair of boots. Try a wide-leg wool pinstripe with pointed-toe dress boots, topped with a silk blouse, or navy dress pants with a crisp white button-down and brown riding boots.

Skirts are a bit trickier to wear with boots, but I think the look is chic and stylish if done right. Like this photo, where I am wearing a short tan leather skirt, simple tee and oversized cardigan with my heeled suede boots. This is appropriate for work or the weekend. Pencil skirts are also the perfect shape to wear with knee-high boots, and the look slims the figure as well. Top the skirt with a blouse, button-down or lightweight sweater for the office. Skirts that hit mid-calf also make a good knee high boots outfit. This style of skirt can be worn with a flat or heeled boot, depending on your destination and style preference.

And don’t let anyone tell you that you can’t wear boots with dresses. Of course, it has to be the right dress and the right boot, but imagine looking super chic and sexy in a slim LBD and knee-high stiletto boots! Those same boots would look great with a classic wrap dress as well. Just don’t pair ruffles and lace with moto boots (unless that is clearly your aesthetic), or summer florals with any knee boot at all!


  • Knee-high boots look best when fitted well. Look for styles that hug the ankle and calf and don’t bag or sag.
  • For women with larger calves, look for boots that have a wide calf or shaft, so they don’t pinch and help look legs look longer and leaner. Thicker or wider heels or wedges can also help balance out larger calves.
  • Thin calves can be disguised with details like buckles or straps that draw attention away from the calf. Boots that tie are also a good option, as they can be cinched in to fit thinner calves.
  • For shorter women, look for boots that have a higher heel or wedge to elongate the leg. You’ll also find that rounded or pointed toes will also help elongate, so steer clear of boxy or square-toed boots.
  • When dressing for the office, stick to classic, riding or dress boots. Leave the moto boots, Uggs, and other casual styles for weekend wear.
  • For a more boho look, opt for slouchy boots, suede, or laces.
  • Pant length should be about ½ to 1 inch off the floor, with a bit of a break where they hit the boot. (For wide length pants, go slightly longer, so only the toe of the boot peeks out.)
  • Wearing a patterned or colored tight with your skirt and dress can add some personality and texture to an outfit.

Are you ready to get those boots out of the back of your closet and give them a chance? I hope I’ve given you some good knee high boot outfit ideas to get you started!

If you need more outfit inspiration on other boots styles make sure to take a look at 20 Stylish Ways to Wear Boots! And if you’re looking for more fall outfits for your style inspiration take a look at my fall outfits category!

Stay Stylish!

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how to wear knee high boots - fall - Love these outfit ideas and style tips on how to wear knee high boots