Due to their length and distinct design, high-top boots can give your favorite outfit a more commanding presence. There’s an added challenge, however, when it comes to learning how to pair these boots with more than one outfit.

Since high-top boots come in different shapes and materials, as well as different lengths like knee-high and thigh-high cuts, some boots might look and fit better with certain garments. It’s also a matter of choosing when exactly to wear them, like for a date or dinner party.

But if you’re able to overcome this fashion challenge, you’ll have no trouble flexing a gorgeous pair of high-top boots and adding flair and sophistication to your fashion sense. Whether you’re working with knee-high boots, combat boots, or cowboy boots, here’s a guide on the most flattering outfit options:

Tights

Tights are versatile undergarments that complement a wide range of outfits. They can make your office attire look more professional, add elegance to your evening wear, and even give your casual winter ensemble a cozier touch.

Tights also work well with a variety of high-top boots since they provide you with full leg coverage. A good pair of tights will make it easier and more comfortable for you to wear thigh-high boots, desert boots, and Chelsea boots.

Tights also come in many colors and designs. Knowing that, you can create a variety of boots-and-tights combinations that won’t fail you in any fashion situation. If you own a pair of auburn wingtip boots, match these shoes with super opaque black tights. This way, the tights can highlight the color of your boots and make them stand out.

On the other hand, if you’re looking for tights that match your black platform boots, petite fishnet tights may do the trick. They’ll highlight your footwear and add an adventurous and feminine touch to your ensemble.

Dresses and Skirts

Pairing high-top boots with dresses and skirts can be intimidating at first, especially because their styles and lengths may clash with one another. Fortunately, there are plenty of ways you can mix and match your high-top boots and apparel to create incredible looks. It’s just a matter of understanding what looks good with your boots and experimenting a little to see that for yourself.

Combat boots, for example, can be paired with a chic plaid mini skirt or a form-fitting, above-the-ankle maxi dress.

The boots’ rugged design creates a great contrast to the elegance of the flowy pieces, resulting in a fierce look that perfectly combines the two different styles.

Velvet over-the-knee boots, on the other hand, pair well with circle skirts and flowy midi dresses. When worn with a circle skirt that falls just above your knee, the boots will seamlessly blend with the skirt’s length and make your legs appear slimmer and longer. When the boots are paired with a floral print midi dress with side slits, on the other hand, your outfit will be able to achieve a more dramatic flair because the slits will reveal your boots when you walk.

Shorts

Shorts are the easiest clothes to pair with high-top boots. Since they don’t have as much length compared to jeans and capri pants, they won’t take the spotlight away from your footwear. This will allow you to confidently flaunt a variety of high-top boots, from lace-up stiletto boots to heavy-duty hiking boots.

However, if you want to convey a specific style, there are certain shorts and high-top boots combinations that you should turn to.

For example, if you’re trying to pull off a grunge aesthetic, pair your oversized shirt with baggy, distressed black denim shorts and black combat boots. This outfit will allow you to de-emphasize the silhouette of your body—which is a characteristic of 1980s grunge fashion.

Different Types of Jeans

Boots and jeans are a classic style combination. However, if you’re working with high-top boots, you’ll need to make sure that you’re pairing them with the right type of jeans so that you can create stylish, yet comfortable outfits.

Some high-top boots might not pair well with certain fits and cuts of jeans. That’s why you should consider the following when pairing jeans with high-top boots:

Skinny jeans

Also known as slim-fit jeans, skinny jeans are known for their tight-fitting style that can be seen from the waist straight down to the ankle. Because skinny jeans are snug on the body, they are easy to tuck into higher-cut boots like over-the-knee boots and tall boots.

Boot cut jeans

Boot cut jeans are designed to flare out slightly at the ankle. As a result, they can accommodate boots with thicker or wider designs like cowboy boots, winter boots, and work boots.

Straight-leg jeans

These jeans are designed with a straight cut from the waist to the hem. Their ankle portion also doesn’t taper. These designs make straight-leg jeans a perfect match for Chelsea boots and duck boots.

As you can see from the tips above, styling your favorite pair of high-top boots with a variety of outfits doesn’t have to be difficult. Use these suggestions to build show-stopping ensembles that can be your go-to looks for a variety of occasions.

Disclosure: This article, other beauty and fashion tips on SheBegan are contributed by experienced fashion professionals, beauty & cosmetics experts. Read our full research and editorial process here. Also, our posts may contain affiliate links, read our full affiliate disclosure

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