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How to Wear High Top Sneakers -So Many Options

How to Wear High Top Sneakers -So Many Options

High-top sneakers are a classic athletic shoe that was invented for the game of basketball and has stayed through the trends and become a casual “sport” shoe, and even a fashion piece to many.

One evergreen when it comes to high-top sneakers is the Chuck Taylor All Star from Converse. The other one is the Nike Air Jordan 1 Mid. Both styles are omnipresent in the street style scene and are almost considered a basic items in your closet.

While they have become popular, it is important to note that, unlike many low-top sneakers, this variant does not agree with every fashion piece or outlook.

How to Wear High Top Sneakers?

The high-top sneakers are a timeless piece that has stayed afloat trends over the years and has shown some sort of flexibility in style.  High-top sneakers can be worn with a dress, shorts, or types of denim. The sneakers come in two variants- the thin and big sneakers. The thin such as Converse Chuck Taylor sneakers are those that give little or no cushioning support to the ankle. Meanwhile, the big high tops are those that have cushioned support for the ankle. They exaggerate the size of your legs giving visual weight to your legs. 

Skirt, Dress, Jeans? What goes with High-Top Sneakers?

Almost every combination is possible, lets have a closer look at some of them:

Skinny Jeans

This is a classic, unisex ensemble for high tops. Whether thin or big, wear your high tops with skinny jeans. This combination looks its best when combined with cropped or three-quarters skinny jeans. 

It gives off a great look when some area of your skin is exposed. What this means is that if you can, ensure that the jeans and the high tops do not overlap. This is not to say that when they do, it is a fashion blunder. No! This only helps to optimize the look. 

Also, pay attention to the colors. Ensure that both pieces do not have the same color especially when they have to overlap. Except, of course, it is black. Black is classic and is in a league of its own and so is allowed to break rules at will.

Again, play safely with colors. A pair of black jeans should be matched with colored high tops and colorful jeans can go with calmer shoe color.

This rule seizes to apply only if the top or shirt is the deal-breaker. Note that the crux of the rule is that one piece is highlighted.

Generally, skinny jeans and your high tops are a very contemporary combination.

Run a tee over it with a pair of sunshades for a simple and classy casual look. This look works for both men and women.

Boyfriend Jeans/ Wide-leg Jeans

This is also a good match with high-top sneakers depending on the look you intend to pull off.

If you are pairing the sneakers with not-too-big straight-leg jeans, it is Ok to keep them a few inches above your ankle either by pin-rolling, rolling, or folding them up.

Or you could go for naturally high boyfriend jeans. Again try as much as possible to show some skin for a clean and fashionable look. 

With this look, you can decide to wear the same color or shade of trousers as your high tops.

Monochromes are allowed. One rule of thumb is never to pair pants with wider legs with big high tops.

By now, you should know what is meant by big high tops. Only combine big trousers with thin high tops.

This tip goes for both men and ladies. Rock your high tops with wider leg trousers, be it chinos, jeans, or any other trouser type.

Short dresses & Midi Dress

This is a style that never goes wrong, whether a fitted gown on big high tops or a flowing gown on thin high tops. A short dress and high-top sneakers will look chic, classic, casual, and every other look you want, depending on how you style it. 

You can substitute a gown with a skirt, it still gives the same result, provided that the skirt is short too. This style for women will highlight the legs and make them look long and lean.

Don’t forget about the midi dress in your closet. Midi dress, jeans jacket, and high-top sneakers, and you are ready to go. A classic dress appears then more casual, sporty and it’s an easy everyday look.


This is another perfect combination. Generally, a high top with a piece that exposes some skin is a big Yes! This trend will never go extinct whether for males or females. 

A big shirt on a firm short, slightly tucked-in will look incredible on anyone not minding your body type. Likewise, big shorts combined with camisoles, tees, round necks, or just any skimpy top.

For guys, this is especially a good option when you do not feel comfortable wearing your shorts with sandals. White socks, shorts, and high-tops not an issue anymore. One of the latest trends put the white sports socks back into the business and sends a friendly reminder to the 80’s style.

Pairing shorts with high-top sneakers are super modern and is considered evergreen as it highlights the legs. With any of these, you are set to slay during summer.


Slack and high tops are also a good choice. The look gets a sporty touch and the slacks can be worn to almost every occasion. Slacks are carrot fit trousers usually worn for business.

Just pay attention, that the trouser is not lying on top of the shoe but that there is a bit of space.

So if you are usually wearing low-top sneakers with your slacks, you might need to shorten them a bit.

Frequently Asked Questions about High-Top Sneakers

What effects do high tops have on the outlook of the body?

Well, it depends on how it is being combined. If combined with big, long trousers or a skirt, then it may look drowning. It can drown the body making it look fatter and round. But in the case where some skin is allowed to breathe in between the shoe and the trouser, gown, or skirt, then the real dimensions of the body can be seen.

How can I choose a high top for my outfit?

First, consider the look you intend to make and the effect that the rest of your clothing will have on you. Your look will only be appealing to the eyes when there is some sort of harmony between your pieces. Choose high tops that complement the color and style of your outfit as well as the magic you intend to create with the look.


There are countless numbers of ways to style your high-top sneakers. This is one reason our love for high tops has stayed resilient through several years, seasons and trends.