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Trending · February 17, 2024

25 Chic Ways to Wear Knee High Boots in 2024 Every Woman Must Try

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Knee-high boots are functional and classy. Since they go a little higher up on your leg, they keep you even warmer. Aside from that, they are also very stylish.

When it comes to style, knee-high boots are also very versatile and can be worn with several closet pieces.  In case you’ve been wondering how to style them, here are some of the best outfit ideas on what to wear with knee high boots:

Table of Contents

  • With skinny jeans
  • With a sweater dress
  • With a plaid skirt
  • With a shift dress
  • With a crochet top
  • With a fit & flare dress
  • With shorts
  • With knee-length dress
  • With a pencil skirt
  • With a structured coat
  • With a duster
  • With a denim dress
  • With a denim skirt
  • With leggings
  • With a pleated skirt
  • With a midi dress
  • With a shirtdress
  • With a blazer dress
  • With a trench coat
  • With a suit
  • With a leather jacket
  • With a corduroy skirt
  • With a slip dress
  • With a leather skirt

With skinny jeans

skinny jeans with knee-high boots

Since skinny jeans follow the exact shape of your leg, they are easy to wear with your knee-high boots.

Of all the types of denim, skinny jeans are some of the most common wardrobe pieces because anyone can wear them. They are simply effortless since they can be styled with any top, any coat or even footwear.

With a sweater dress

Knee-high boots outfits with white sweater dress

If warmth accompanied by coziness is what you’re looking for, then what better way to go about it than wearing a sweater dress with knee high boots?

Sweater dresses are often so snuggly and come in different lengths and designs. You probably will have to go for a longer one if you prefer that extra warmth, when it’s extremely cold outside. Pairing one with knee-high boots will also make the whole look very stylish.

It’s always a great idea to grab knee-high boots in a color that can be found on your sweater dress, if your sweater dress is multi-colored.

With a plaid skirt

knee-high boots, and a plaid skirt

Plaid is a great print that’s mostly worn during the fall. It’s great and fun and if you want a more youthful look, then a plaid skirt is the way to go. Pair that with some knee-high boots, and you have an amazing look for the cooler fall weather.

Remember, since plaid is a pattern, you have to be very selective with the colors you pair it with and in most cases, plain boots are better.

With a shift dress

shift dress  knee-high boots

Wearing knee high boots with a shift dress is one of the most forgiving outfits suitable for any age group and body type.

Shift dresses are flattering, considering they are meant to be that loose. Wearing one makes you feel more confident, because it hides your “weaknesses” that you might be self-conscious about (such as a bulging midsection or wider hips or thicker thighs).

You can pick the length you prefer most with a shift dress whether long or short.  You can also choose from different colors and wear dresses with some knee-high boots.

With a crochet top

 knee-high boots, a crochet top

When wearing knee-high boots with a crochet top, you’ll have a chic look for the spring or fall that could easily take you from the office to an event.

With a fit & flare dress

knee-high boots with black leather jacket and fit-& flare dress

A fit n flare dress is one of the most flattering, considering it cinches your waist, which is the smallest part of your body, then flares out towards the bottom. They are great when worn with different types of shoes including knee-high boots, in fall weather.

It’s a fun flirty look that works for different body shape. These dresses come in different lengths and even volumes, but they all look really good with knee-high boots.

With shorts

knee-high boots With shorts

One of the best outfits for transitioning weather is to wear shorts with knee high boots.

Shorts are great especially during summer months, as they allow you to show off your legs. They come in different lengths, which gives you the flexibility to choose anything you prefer.

For the best fall look, it’s worth going for longer shorts, as they are more appropriate for the weather and make more sense when styled with such boots.

With knee-length dress

knee-high boots with knee length dress

You may be thinking dresses are great with strappy heels, stilettos and sandals, but in the cooler months, they also go well with some knee-high boots considering their simplicity.

Straight knee-length dresses that come in simple design are great for office environments and more formal environments. The boots just make them more interesting.

This look can be generally minimalist, if your dress is in neutral colors like above. Should you go for a more colorful dress, it’s best to pick plain knee-high boots in basic colors like white or brown.

With a pencil skirt

black knee-high boots  With a pencil skirt

Pencil skirts are some of the most flattering silhouettes you can find. They also follow one’s figure, highlighting your hips and giving you a smaller waist. They are also some of the pieces that look really great with a pair of knee-high boots.

With a structured coat

knee-high boots with single-breasted long blazer

A structured coat is a must-have piece in any woman’s wardrobe, and they are such a great item to wear with any of your tall boots. You can go with a shorter dress or skirt underneath, and show off your beautiful legs!

With a duster

black knee-high boots With duster

A duster is one item that’s great to have. When worn with a pair of knee-high boots, you get a great outfit that makes your look edgier, whether the duster is worn over a skirt or dress.

The flowy nature makes it a great layering piece that makes an otherwise plain and simple outfit look more elevated. Since dusters are long, if you’re wearing something colorful underneath your duster, make sure the duster is nice and plain.

With a denim dress

 black knee-high boots With a black denim dress

A denim dress can be styled with different types of knee-high boots for the chic and casual look in the fall.

Denim is always so comfortable and flattering, whether we’re talking about a denim shirt, jean jacket, pants, or even a dress. The denim fabric goes with a number of different materials such as leather, and suede, just to mention a few.

With a denim skirt

knee-high boot outfits with Denim skirts and long coat

You can wear your denim skirt with knee-high boots for a classy outft for the fall or the spring when the temperature goes up and down.

A denim skirt never goes out of style and can be worn throughout every season within the year, depending on how you style yours. They can be paired with different tops and most of all different footwear, whether casual or dressy.

With a blue denim skirt, it’s easy to pick boots since these go with boots in just about every material and color.

With leggings

black knee-high boots with brown leggings

Since leggings follow the shape of your body, they’re one of the easiest to wear with knee-high boots, especially if the leggings are plain.

Leggings are comfortable, which is why many of us like to stock them up in their closets.  They are great for lounging around, but there’s a particular style that can be worn outdoors.

With a pleated skirt

Knee-high boots outfits Pleated mini skirt and jacket

In the fall, knee-high boots will add some casual touch to your very feminine outfit.

Pleated skirts are a classic wardrobe staple that can make you feel more ladylike, especially if they’re longer length. You can choose from a knee-length , midi or maxi pleated skirt for this look.

Pleated skirts are mostly preferred for dressy occasions such as high teas, high profile events, church, and many such. However, you can wear them on ordinary days too, when you wear them with tall boots.

With a midi dress

wrap midi dress and knee-high boots

In the fall, you can wear a midi dress with some knee-high boots for extra warmth.

A midi dress is ever so classy, because of the length. Also because of the length, they requires more thoughts to style. Tall boots can indeed make midi dresses look more flattering for most women, because they eliminate the gap between the dress hem and your boots, thus avoid making your legs look cut-off

With a shirtdress

knee boots With a shirtdress

One way to look smart casual is to wear shirt dress with knee-high boots.

Shirtdresses are known to be those wardrobe pieces that leave you looking smart. They come in different styles and lengths which gives you a lot of flexibility to choose according to your preference. Beside looking formal, they can also be dressed to look casual and even edgy.

With a blazer dress

knee boots With a blazer dress

One great way to wear your blazer dress is with a pair of knee-high boots, preferably simple ones.

A blazer dress, just like an actual blazer, gives you an elevated look that is classy and sophisticated. Blazer dresses are even easier to wear, considering you don’t have to worry much about what to mix and match it with.  

With a trench coat

knee high boots outfits With a trench coat

You can wear longer trench coats fully buttoned or tied and pair with knee-high boots for a Parisian look.

Trench coats are a wardrobe staple, a classy style that never goes out of style and are also functional.  They come in different lengths, allowing you to choose the best one according to your height and your style.

With a suit

knee-high boot With a suit

You can wear your skirt suits with some knee-high boots for a fun and trendy look.

A suit is a must-have, if you love the style to feel and look both sophisticated and elegant. Whether you wear a pantsuit or a skirt suit, you can always be assured of that classy outfit.

With a leather jacket

knee-high boots outfits- denim skirt with moto jacket

Leather jackets are versatile pieces that you can always throw on for a cool urban vibe. When you wear them with your tall boots, you instantly look edgier!

With a corduroy skirt

knee high boots outfits with turtleneck top

Corduroy skirts are great pieces for transitioning weather, especially in the fall, but of course, you can wear them year round. Wear them with your tall boots will not only make you look more chic, but also give you extra warmth.

With a slip dress

knkee-high boots with high-low dress

Slip dresses are gaining momentum in the last several seasons, and you can pair them with your tall boots for an expected look. This will for sure turn heads wherever you go, as it makes quite a fashion statement!

With a leather skirt

knee-high boots with leather skirt and cardigan

Leather skirts are one of the easiest pieces you can wear with your tall boots, because both are favorites of many women, especially for when the weather turns colder.

Posted In: Trending

Hello there! My name is Chi Li, 5'2", founder of PETITE DRESSING, the clothing line for women 5'4" & under. Are you petite and have you been frustrated with what to wear?
This is an issue few truly understand and even fewer brands truly address.
Being petite myself, I have been writing about fashion for short women since 2016 and my brand petitedressing.com has touched the lives of millions.
My styling concepts for petite women not only focus on the perfect fit but also on flattering & elongating the petite frame for a lean silhouette, optimizing the proportions.
Shop my clothing line here.

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