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How to Wear High-Tops With Jeans

Model wearing jeans and high-top white sneakers.

If you are looking for a cool, sporty, slightly edgy look, nothing looks better than high-top sneakers with jeans.

As a lover of jeans and high-top sneakers, I believe that this fashion-forward duo makes a style statement that can up the ante on any casual look I am sporting, whether I am going to get the groceries or having a game of basketball with my friends in the evening.

However, the best thing about them is that they are super comfortable and versatile and can match a whole range of streetwear.

High-tops alone can result in a strong visual appearance; however, when coupled with a pair of jeans, they have the potential to become a showstopper.

History of High-Tops

High-top sneakers were first introduced in the early 20th century and fast became the shoes of choice for basketball players.

When Spalding first developed the shoes, they were made of a thinner rubber sole as compared to the Converse All-Star shoes that were introduced in 1917. According to sources, the high-tops were inspired by the ankle boots worn during that time.

However, over the years, high-top shoes gained a reputation for supporting the ankle, preventing injury while playing sports. In time, these shoes paved their way from the basketball courts to the runway and made a mark in the footwear industry as one of the most fashion-forward shoes.

Today, high-tops are considered an expression of style and can easily steal the spotlight from any outfit.

A Fusion of Contemporary Fashion: High-Tops with Jeans

Unisex streetwear fashion shoot featuring plain white sneakers.

If we talk about current fashion, high-top sneakers are the go-to footwear for all genders. These sneakers are versatile, cool, and go with practically every casual outfit — most notably jeans.

Currently, the modern fusion of high-tops with jeans is fast becoming a basis for a casual voguish style. It is a very smart way to give yourself a chic laidback look that completes your street look. Wearing high-tops allows you to flaunt several different types of looks when paired with various jean outfits, be it street style, sporty, or preppy look.

Basics of Styling Jeans with High-Tops

Before I recommend some of my favorite jeans with high-tops style, let’s take a look at some style basics:

  • The high-top and jeans look offers you an urban and edgy look. This doesn’t mean that it doesn’t work for casual smart looks. In fact, high-top sneakers and jeans are a staple for this kind of style. However, you cannot wear it for formal events.
  • Make sure you keep your high-tops clean, especially the laces. Dirty sneakers reduce the overall look of your entire outfit and give you a sloppy look rather than the classy street look you are going for.
  • People usually opt for a length of jeans that is above the ankles to show off the high-tops. This look works very well as it allows tiny glimpses of the skin and looks really stylish.
  • If you want to increase your comfort, wear socks with your high-tops. Most people usually go for no-show socks that stop just beneath the ankle. You can wear long socks if you are wearing shorts but for jeans, no-show socks work better.
  • If you want to create a business casual style look, I recommend that you pair your high-tops with slim-fit jeans. They look more dressy and smart. However, this doesn’t mean you cannot rock your sneakers with other types of jeans. It just depends on how you style them.
  • To give your outfit an upscale look, you can pair different types of leather jackets with your ensemble.

Now, let’s get started with some of my favorite styles for men and women:

For Men: High-Tops with Jeans

Chic man walking down a metropolitan street in white sneakers.

Pairing high-tops with jeans is a great way to portray a smart and sporty look. The outfits I am recommending change according to the different types of jeans you are wearing. Let’s take a look.

Slim Jeans with High-Tops

Slim and skinny jeans are one of the very best trousers to wear with high-tops. Slim jeans with chunky high-tops can offer you a slimming effect and make short legs look longer. A slim-fitted black pair of jeans with a solid-colored t-shirt or crew neck shirt, topped with a black leather jacket at once gives a chic and effortless vibe.

If you want to go for a more street look, pair slim jeans and high-tops with a simple white t-shirt and an open checkered shirt for a simple and super-casual look. For a slightly formal look, you can wear high-tops and slim jeans with a dark button-up shirt and cream or tan blazer — a perfect ensemble that looks smart and chic but not pretentious.

Loose-Fit Jeans with High-Tops

On a model wearing corduroy pants, white high top sneakers.

Some people think that loose-fitting jeans with high-tops are a no-no. However, it is one of the most popular urban fashions. Baggy jeans that fell on top of the high tops of your canvas high-top sneakers are the “in” thing on the street.

If you do not like your jeans hiding the top of your sneakers, you can opt for slightly cropped jeans that cut off at the ankle. This way, you can show off your high-tops to the maximum and your jeans will be well out of your way without having to fold them upwards.

To make a statement outfit, go for dark-washed jeans with bold black and red high-tops. You can pair this ensemble with a plain white t-shirt with a denim jacket or even an open patterned button-up shirt.

Straight-Legged Jeans with High-Tops

Straight-legged jeans with high-tops give you a cool, sort of normcore look and add a wow factor to the standard jeans and T-shirt combo. In terms of smarter, semi-formal styling, you can opt for beige or navy jeans with high-tops and pair them with a nice Oxford or polo shirt.

Keep your shirt untucked and if you want, cuff your jeans neatly so that you can show off your sneakers.

This is a great smart-casual outfit for Sunday brunches or other casual or semi-formal weekend events.

Straight-legged jeans allow you to try on a variety of styles since they are neither baggy nor skinny and their silhouette flatters people of all shapes and sizes. Because of its versatility, you can try various different types of high-tops with straight-legged jeans and they will give you a different effect each time.

Cuffed Jeans with High-Tops

White high top sneakers worn casually by the model.

Want an urban look with an effortless no-fuss style. Pair bright white high-tops with slim cuffed jeans. Depending on your preferences, you can either roll your jeans a couple of inches so that they just reveal the top of your sneakers or you can roll them up a bit further up so that they show a couple of inches of skin.

Pair this ensemble with a solid-color or white T-shirt for casual day wear.

Aside from white high-tops, you can also use black high-tops, red high-tops, or high-tops in different colorways. However, make sure that if you are wearing a lot of bright colors below, you should keep your top apparel, i.e. your shirt and/or jacket low-key in a single white or neutral tone.

Jean Shorts with High-Tops

High-tops with jean shorts? Sounds slightly off but it is actually a great way to show your athletic but quirky personality. For men who work hard at the gym, it is a great way to show off their sculpted leg muscles.

If you want to add a goth look to your outfit, choose black jeans shorts and a black hoodie or sweatshirt with black high-top sneakers. Alternatively, you can also choose white high-tops with blue jeans shorts and a hoodie-style jacket for a fun and youthful vibe.

If you want to go for a more vibrant vibe instead, choose blue denim shorts with high-tops and mix them up with a vintage t-shirt and a lightweight shirt jacket for a comfortable and hassle-free look.

Since high-tops are designed to fit close to the feet, they look great when contrasted with baggy shorts and loose T-shirts, giving you a very 90s skater-boy vibe.

For Women: High-Tops with Jeans

High top sneakers flying above a cityscape.

Originally, high-tops sneakers were the domain of men; however, this trend was very soon followed by women. Just give Instagram a glance and check out how women have now owned this streetwear style.

Skinny Jeans With High-Tops

Skinny jeans with high-tops are a staple for fashion-forward women. These days, young girls and women of all ages are seen pairing black or blue skinny jeans with high-tops, along with simple or printed T-shirts, cropped tops, off-shoulder tops, casual button-ups, and even short flared blouses.

For a funky look, you can style your skinny jeans and high-tops with tops in bright and bold colors and patterns. In fact, for women, styles with skinny jeans and high-tops are virtually endless. To make a statement look, choose a leather bomber jacket in red or black to wear on top.

Baggy or Wide-Legged Jeans with High-Tops

Female legs wearing sneakers against a yellow background with flowers.

For warmer days, relaxed and wide-legged jeans are more appropriate. You can either let your baggy jeans hang straight down on top of your sneakers for a more disheveled urban look or neatly fold their hems back to give a tidier look. Alternatively, you can switch your baggy jeans for wide-legged jeans.

This ensemble can also be a great choice for a casual date night. Just choose a pretty silk ruffled blouse with wide-legged jeans and black and white high-tops for a cute, flirty look.

Cropped Jeans with High-Tops

For an edgy vibe, try on a cropped pair of jeans with black or white high-tops paired with a crop top or a bandeau top. Add a ripped denim jacket or a hoodie jacket to complete the look.

The great news is that tops in any color or pattern will go with the simple blue cropped jeans and high-tops but I recommend choosing plain white ones so that your entire outfit pops out even more.

Jeans with Denim High-Tops

Fashionable young model wearing popular Italian denim and pricey white retro sneakers.

Is there such a thing as too much denim? I have seen many people rock the full-denim look with a denim shirt, blue jeans, and yes, even denim high-tops. If you are not a fan of uniformity, you can use contrasting colors or light or dark shades for each item of your item.

For example, light blue denim high-tops can be worn with washed dark blue jeans. You can complete the outfit by wearing a light blue denim shirt or a black denim shirt. Alternatively, you can choose another material besides denim for your shorts.

A simple white tee can look just as good, but one of my favorite looks is to add a black and white striped t-shirt with a bright red woolen scarf. This outfit looks chic yet effortless and is a great choice for a lunch date with friends.

Distressed Jeans with High-Tops

For an edgier and slightly avant-garde look, nothing works better than distressed jeans over high-tops. Team up a pair of ripped blue jeans with white high-tops, a black halter top or tank top, and a maroon or dark brown leather coat for a cool and sensual look.

Another one of my favorite looks is with slim ripped jeans, coupled with white or denim high-tops, a light grey Henley top, and a long soft shrug in a neutral tone. If you want to amp up the outfit, you can switch the shrug with a camel or tan-colored blazer, just like Cara Delevingne here.

The Bottom Line

White sneakers against a white background.

High-tops are very versatile; they can make your feet appear smaller if you tie the laces up till the end and if you opt for chunkier versions, they can make your feet appear bigger. Neither look is better than the other. It all comes down to how you style it.

Since high-tops are very urban footwear, we think they work best with various types of jeans — another staple casual apparel.

Both high-tops and jeans are extremely versatile items of clothing, which means the choices for styling them are endless. My favorite styles are above, but there is always room to experiment. The main thing is that no single style may look good on everyone — so you should rock the styles that you feel the most comfortable in.