A gentleman’s guide to High top Sneakers

High top sneakers are an enduring trend and a must-have item in every stylish Gentleman’s closet.

If you’re trying to achieve an overall look that is somewhere between professional and laid-back without coming off as overly casual, it’s just the thing for you!

But what’s so great about these sneakers? Keep reading to find out more.

What are High top sneakers?

High top sneakers commonly called ‘High tops’ are sneakers that extend above your ankle.

High tops look great on every man, regardless of age. However, they tend to be favored by the young, urban, and stylish.

A Hundred years of history

Converse made the first of sneakers in 1917. These were the world’s first high tops. After Chuck Taylor, a basketball star of the 1920s made changes to the Converse shoe design and endorsed them; they came into mainstream basketball use.

Popularity of High top sneakers

Every time Michael Jordan stepped onto the court during the ‘85 season, he was fined $5,000 for wearing the first Air Jordans.

The red and black sneakers were a stark contrast from what his Chicago Bulls teammates were wearing and David Stern, an NBA Commissioner, wasn’t having it! However, Jordan kept wearing them.

The ban, besides denting the pockets of whoever was paying those fines all season, popularized high top sneakers for many years to come.

For a long time, High top sneakers were used almost exclusively in basketball before slipping into everyday fashion culture. Today, high top sneakers can be found in literally every shoe store in the country!


The rise of High tops in modern fashion

High top sneakers are constantly being innovated. Your favorite rappers and other popular celebrities often collaborate with High top makers to make their own line of shoes.

For example, Drake has partnered with the Jordan sneaker brand to design his own OVO line of sneakers. As expected, these models were rushed off the shelves by his fans immediately after they were released.

The good news is that there’s a wide range of high top sneakers available for you to choose from regardless of what budget you have.

How to wear High tops

Men’s fashion can look ridiculously simple, but it takes a conscious effort to pull off a great look.

Fortunately, whatever the occasion you’ve got or your personality type, high top sneakers are versatile enough to help you do just that.

Here are three great looks you can achieve with a good pair:

The Professional

You might want to go with a long-sleeved shirt rolled up and tucked into jeans or chinos pants and donning your favourite high top sneakers. 

This outfit would give you that ‘sophisticated’ look you often see with fashionable engineers and computer programmers. It’s a bold, yet professional look that makes you look gentlemanly with a little charm and poise.

The Trendy

You can achieve a semi-formal look by pairing your high tops with a dark-colored leather jacket for a sharp, trendy look.

Trendy outfits like these could help you slip from formal into informal settings effortlessly. Wearing a cool pair of sunglasses with this look when outdoors will be the icing on the cake!

The Spontaneous

If you want to go fully informal on that vacation or outdoor shindig, shorts, a vintage shirt and a nice hat could be a killer look with your high top sneakers.

The hoodie, jeans, and high tops combination is another uber-cool look that doesn’t make it seem like you put in too much effort to choose your outfit.


Choosing your high top sneakers

There are many important factors to consider when choosing a pair of high tops.

In a moment, let’s review to a few of them:


Color palette

Although some of our favorite celebs are notorious for having a ridiculous number of sneakers of the same color, we advise that you vary the colors of your collection whenever you can.

So, what range of colors should you fill your shoe rack with? While that’s entirely up to you, some colors work quite well with most outfits.

Grey, white, brown, and black colored sneakers are great if you just want to keep a low profile or maintain the subtle, elegant appearance of your clothes.

Brightly colored or patterned sneakers tend to draw more attention and are a perfect choice if you want to make a statement!

Size and fit

Size and fit are two absolutely important factors to consider when choosing a pair of High tops.

Taller people tend to have problems finding the right size of footwear to accommodate their larger feet because most footwear is designed for the majority of the population.

Some people have slender and long feet, while others have wider feet. Many footwear companies manufacture shoes for the majority foot sizes in order to stay profitable.

Also, everyone has a unique foot type. To find out yours, simply take a look at the point where your leg joins with your foot (called the foot’s arch)

You can see that you either have a:

  • High arch
  • Normal arch
  • Low arch (flat foot)

If you’re flat-footed man like me, you’ll want to choose a shoe with more structure, better arch support, and moderate cushioning. There are ready-to-wear models available for every foot arch type.

If you’re still having trouble finding the perfect size and fit, it would be great to have your High-tops designed for you.

Quality of construction

While there is a rapid rise in the volume of high tops in the sneakers market, lots of sub-standard footwear are also being produced in commercial quantities.

Fortunately, if you know what to look out for, you could avoid buying a crappy pair of shoes.

Here are a few tips to help you spot a high-end or low-end pair of high tops…

To identify a low-end pair you have to look into the fine details of the footwear.

  • Check the soles; do they crack when you try to fold the shoe?
  • Take a look at the seams; are they already showing signs of coming undone?
  • Have a feel of the insides; how comfortable do they feel?

These few questions are a good mental checklist to use before buying a pair of high tops.

A high-end crafted pair can be subjected to these stress tests and still hold up properly.


Before you make a buying decision, ensure that your high tops are made of original materials that outlast the price you pay for them.

If you’re buying a pre-designed shoe, it never hurts to ask the seller about the materials it’s made of. You can also do your own research on quality shoe materials to be double sure.


Another very important factor to consider is the brand of sneakers you want to get. Having a go-to brand that suits your needs perfectly will save you a lot of time and stress involved in putting together a great outfit.

Choosing the right brand

If you’re loyal to some of the popular brands, then you probably already have your answer.

But have you ever considered what it would be like to design your own cool pair of high tops? And no, you don’t need to be a celebrity to do that.

If you’d like to stay elegant but still retain your identity, you can have a custom pair of High-tops crafted just for you. You could even brand it with your initials to make it one of a kind!

Sport a Super cool look with Custom made or Pre-designed High Tops

If you’re a sucker for premium shoes like we are, you should look for a footwear store where you can order high-end pre-designed sneakers or design your own cool pair of high top sneakers to match your unique outfits!