12 Classic Sneakers for Men

The rumble in the jungle goes down as one of the most classic fights in modern history. In one corner, we had the boisterous Ali in his prime—who truly moved like a butterfly and stung like a bee—chopping down veteran boxer George Foreman like an ax to wood.

This was Ali’s Magnum Opus. The one true fight that cemented his name in the crypts of boxing legends. And redefined the meaning of the word ‘classic.’

The Era of the ‘Classic’ Sneaker

According to the online dictionary, a classic is some ‘thing’ or some ‘event’ that has been judged to be one of a kind over a certain period of time. Its potential to change the world is unrivaled. It influences the cultures of millions of people and leaves a long-lasting impression.

For years, we men have had a special connection to our classic sneakers. It’s one of the few bromances that have withstood the test of time. Let’s face it; whether you’re 60 or 19, you will always appreciate a classic sneaker.

Unfortunately, the term ‘classic sneaker’ has been tossed around so recklessly these days that it’s quickly lost its meaning. That’s why we’re here to set the record straight about retros.

In this piece, we’ll be reviewing the 12 best sneakers for men. We will also be analyzing what to keep in mind when going sneaker shopping. Ideally, we hope this content will help you spot a ‘knockoff’ from the real deal when buying a sneaker. Also, be sure to keep your sneakers fresh and clean – they are precious!

Without further ado, let’s begin.

There’s no epic way to reminisce on the age of skating and punk rock than buying a pair of retro vans checkerboards. These elegant sneakers have no doubt looked magnificent since their inception in the 1950s. You’ll immediately feel nostalgic once you see how the checker pattern fuses seamlessly to these Old Skool sneakers.

In terms of comfort, the sneaker is cushioned so that you feel like you are walking on air. One of the main highlights of these classics is their suede and canvas construction, with a sturdy insole for maximum grip when you’re out and about.

  • At only three pounds, these sneakers are pretty lightweight.
  • Highly cushioned insole for maximum comfort.
  • If you happen to have an extremely wide-foot, you might find these shoes uncomfortable even at your ideal shoe size.

For years, Converse has been one of the leading brands for best men’s sneakers around the globe. One of their most notable sneaker designs are the Chuck Taylors High Tops; in honor of the basketball legend who dominated the sport in the ‘50s and ‘60s. The first thing that greets you once your purchase these sneakers is their trademark outsole.

Crafted from high-density rubber that envelopes the foot, they guarantee maximum protection and durability when you’re out and about. The presence of a slip diamond further improves the sneaker’s grip to the ground; while high-pressure activation provides excellent traction when walking. The removable insole also makes it easier for you to clean the shoe, keeping it fresh for days.

  • The removable insole is crafted from durable rubber for longevity.
  • To maximize traction when you’re walking, the outsole is manufactured from high-quality rubber.
  • There have been complaints about the shoe size being slightly larger than the one being ordered.

The best casual sneakers for men can be found in vans massive collection of shoes. In fact, Vans crafted an entire canvas model for their slip-on; emphasizing a linear, concise design. The VEYE slip-on model comes with nylon stretch strips on adjacent sides of the sneaker so that you don’t have to force your thumb into the sneaker when trying to remove the shoe.

Despite the fact these slip-ons are designed entirely for comfort, they do not fail in the durability department either. A vulcanized rubber construction encapsulating the outsole ensures the shoe remains sturdy for years.

  • The vans are manufactured from vulcanized rubber for extra durability.
  • A full canvas construction of the exterior envelops your foot for comfort.
  • A removable rubber insole for maximum support.
  • The biggest issue with these vans is how fast they wear and tear after using them for a couple of months.

The Gazelle is one of Adidas’ most famous classic shoes. Designed as a theme-oriented sneaker, it comes with a number of color options to suit your preference. The highlight of the Adidas Gazelle is its cushioned insole which enhances comfort and makes you feel like the lightest individual on the planet.

Despite having a rather low ankle-dip, a durable synthetic lining prevents any small obstructions from entering the shoe and making you feel uncomfortable.

  • Extremely versatile with over 40 different themes to choose from.
  • These sneakers are crafted from 100% skin leather taking comfort to a whole other level.
  • The shoes can be squeaky when walking on marble floors.

One of the most outstanding features of PF Flyers Centers Hi is that they’ve remained loyal to their retro look of the 1950s.

That’s not all:

PF Flyers have one off the most stylish uppers on this list making them a top contender for the best sneakers of all time.

If you plan to complement your casual weekend wear, then not only do these sneakers breathe life into your attire, but also enhance its style thanks to the diamond patterned designs on the midsole.

  • Very stylistic design that maintains a retro’s ‘50s look.
  • Lightweight sneaker
  • The shoes are a bit tight and can feel uncomfortable the first few weeks before they expand to accommodate your feet.

Considered a collector’s favorite, the Vans Sk8 is the finest high-top in the market. These sneakers are fitted with a sturdy rubber insole, ensuring your feet remain compact as you walk.

They also come with a waffle bottom to prevent your feet from tiring quickly especially if you’re traversing through difficult terrain.

  • An extra stitching reinforcement ensures that the shoes maintain a great shape throughout.
  • A wide array of themes to suit your preferences.
  • Strictly do not clean/rinse these shoes with water because water accelerates the wear and tear in them.

The classic Adidas sneaker is no doubt one of the most Old-school albeit flashiest sneakers on this list. Not only do these classic shoes for men make you a head-turner at a party, but also cradle your feet delicately for enhanced comfort while out and about.

For such a fashionable shoe, the sneaker is surprisingly sturdy; with a midsole crafted from full-grain leather. Who can dare forget the classic Adidas strip? Not to mention the gold-colored logo? That’s what makes owning these Adidas classics memorable.

  • The classic Adidas triple strip is a head turner and very eccentric.
  • A highly cushioned rubber sole makes the shoe extremely comfortable
  • Despite having a cushioned rubber sole, the sneaker itself is quite narrow around the toes and it can feel a little uncomfortable.

There’s no denying the thrill of owning your own pair of classic Smash V2 Puma sneakers. These shoes come with excellent features such a sturdy rubber outsole for maximum comfort throughout the day.

The diamond weave pattern is also very pleasing to the eye. However, the standout feature for Puma Shoes is that they always come in the perfect size. Plus, thanks to a durable padded collar, your heel gets all the support and comfort it needs.

  • Longevity due to the outer construction being crafted from full-grain leather.
  • The padded collar provides amazing heel support
  • Puma is famous for its perfectly-fitting shoes.
  • Wear and tear are their biggest problem. After a month, the insoles begin to wear and tear.

In terms of quality, Seavees certainly brings its A-game as the Hermosa Standard is crafted from high-quality BF Goodrich rubber. This retro sneaker was a classic in the ‘60s before the company went under for more than half a century.

Fortunately, Seavees returned to production in the mid-2000s, continuing their tradition of high-quality sneakers engraved with their trademark ‘Hermosa.’

  • The uppers are crafted with a vintage finish thanks to a superior navy linen construction.
  • Quite an eccentric shoe for such a fair price
  • Wear and tear are their biggest problem. After a month, the insoles begin to wear and tear.

When the Nike Air Jordan’s first hit the shelves in the mid-’90s, fans were hooked. At the time, buying Air Jordan’s’ was very expensive because of all the hype. So, if you never had the chance to experience them as a kid, you now can as an adult.

One of the standout features of the Air Jordan’s is their firm leather and rubber exterior that pioneered traction padding for high-performance sporting activities such as parkour and basketball. As for circulation, these sneakers come with a breathable mesh interior to keep your feet cool and dry during intense-sporting exercises.

  • The exterior of the sneakers is lined with a breathable mesh lining to enhance circulation.
  • A padded collar provides maximum comfort to your heel.
  • A textured rubber insole guarantees extra support during sporting.
  • The classic Jordan sneaker is still pretty expensive

Converse yet again makes it on the list thanks to their terrific All-Stat Low Top Sneakers. These retro sneakers were designed as the perfect fusion of movement and elegance. Still considered quite iconic in streetwear fashion, these low-tops have over fifteen unique themes to choose from depending on your preferences.

As for comfort, a padded collar protects your heel, while a synthetic insole guarantees a great resting place for your toes. In terms of durability, there is a canvas construction for both the upper and exterior of the sneaker. For longevity, the outsole is crafted from vulcanized rubber that is also a great shock absorber when you’re running.

  • The shoe has over 15 different themes to choose from.
  • The exterior and uppers are made from 100% canvas making it very durable.
  • To improve your stability and ensure longevity, the outsole is reinforced with vulcanized rubber.
  • Not designed for wide feet and can cause discomfort before expanding to accommodate a large foot.

Despite its affordable price, Reebok Royal classics have the finish of a luxury sneaker. The suede interior is designed to massage your feet and make them feel immediately warm and comfortable.

A durable paddled collar ensures your heel sits well in place and prevents any unwarranted injuries. The exterior and upper of the shoes are crafted from nylon and suede, while for maximum shock absorption, the shoe comes with an EVA midsole.

  • The shoes are extremely durable thanks to a suede and nylon finish.
  • The presence of a padded tongue protects your heel from injury.
  • After about a month or two of use, the wear and tear-especially on the outsole-is quite visible.

Consumer’s Guide to Purchasing Classic Sneakers

There are many factors to consider before purchasing the perfect retro sneaker. However, certain factors have a higher priority compared to others.

In this particular guide, we will be discussing the most ideal features to consider before purchasing top men’s sneakers.

The Unspoken Rule of Sneakers: Always Have two pairs

One of the golden rules of sneaker shopping is to always buy two pairs for every classic model you purchase. Each pair of sneakers will serve its own purpose as follows:

  • The “Casual” Pair- This is the pair that you wear during social gatherings. For example, if you plan to head out with friends or try out a new restaurant, then this pair fits the bill. By designating one pair to casual activities, you minimize the wear and tear thus increasing the longevity of the sneakers. Don’t you want your sneakers to look fantastic six months down the line?
  • The Beaters - The second pair should be designated for your adventurous life. Wear them when you plan to go for a short hike, mow the lawn, or take a long walk on the beach. The bottom line is that you’re willing to let this pair get a little dirty.

Be Mindful of Your Age

As much as owning a pair of retro sneakers is great, you shouldn’t buy a pair that doesn’t reflect your age. For example, sneakers like the classic Jordan’s are awesome if you’re in your mid-30s, but not so much if you’re in your 60s.

Fortunately, other sneaker brands like vans and converse factor in all ages in their designs and hence can look amazing on your feet even if you’re a senior citizen. There’s no point in wearing flashy sneakers only to look like you’re going through a midlife crisis, right?

So, consider the right theme, color, and brand of sneaker that complements your age.


Despite the fact that classic sneakers are all about style, they should also be practical. Not all sneakers can be worn, to say, a basketball game or a first date. It is vital that you find a sneaker that suits a certain event or purpose. For example, if you’re purchasing a sneaker merely for style, then it wouldn’t hurt if they are not as strong in features such as sturdiness and durability.

On the other hand, if you’re a sports junkie who plans to use his sneakers on the court or on the field, then look for a sneaker that emphasis on both durability and compactness. Ideally, the best sneaker is the one that looks great both on the court as well as in social gatherings.

Our Verdict

Factoring in all the information we have provided, we believe the best classic sneakers to buy in 2019 are the vans Sk8 High-Tops. Not only are they durable and great for all ages, but also serve as a sport sneaker with a stylistic finish.