Coolest Men’s Trainers - The Ultimate Guide to Investment Trainers


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The 7 Coolest Men’s Trainers of All Time

As blokes, we all have something in common when it comes to men’s style choices. If you’re a Football Manager or a Rocket Scientist, we’re certain that at least once in your life, you’ve experienced the thrill of investing in a pair of the Coolest Men’s Trainers. As I am forever on the pursuit for the coolest men’s trainers, I figured it’s about time we reflected on the Coolest Men’s Trainers of All Time to help you identify the Coolest Men’s Trainers to invest in. 

Nothing beats the comfort, practicality and style offered to us from a simple sneaker or a sports shoe – and in a World without daft dress codes and conventions, I’d happily spend the rest of my life kicking back in a pair of the coolest men’s trainers the World has to offer. 

Collecting sneakers, has become for some Gent’s, a real passionate, past-time. Retro trainers and Rare sports shoes, have become gold dust in some circles of ‘sneakerheads’ and cool trainers like the original Nike Air Jordan 1 (the first edition in the Nike and Michael Jordan collaboration) to the Adidas Yeezy Boost 350, (the creative design project from Kanye West), are topping the list of the rarest and most coveted, cool men’s trainers of all time.

Okay, so I’m not one to splurge thousands on a trainer but I’ll be honest, I did get a little hot under the collar when I heard about the long-awaited release of the NIKE AIR MAG (THE gravity-defying trainers from Back to the Future) back in 2015.


Coolest Men’s Trainers

So, I can totally understand how some rare men’s trainers should be kept in a box and never worn outside the house to maintain their pristine, but honestly, I’m not about that life. Men’s Trainers should be loved and worn and endure every adventure with you! Be it a City Landscape or a Rural Escape, one thing is for sure though – not all men’s trainers are made equal.

Some of the coolest men’s trainers are timeless, stylish and versatile, they’ll always have your back and always keep you looking fresh. With that in mind, I’m excited to bring to you the official Man Wants guide for ‘The 7 Coolest Men’s Trainers of All Time’.

Converse Chuck Taylor All-Stars

Originally released in 1917 as a superior basketball sneaker, the humble Converse Chuck-All Star boasts a 100 year legacy with prominence in sporting industries and popular culture. Worn by icons like Elvis Presley and James Dean, the humble converse high-tops are an indisputable statement in every guy’s wardrobe. A simple staple in classic men’s styling – every guy should invest in a classic pair of Converse Chuck Taylor All-Stars. One of the coolest men’s trainers to take you from work to bar in a blink!

Converse Chuck Taylor All-Stars

Adidas Stan Smith

Before the iconic Nike and Michael Jordan collaboration, there was the infamous Adidas and Stan Smith partnership. When American Tennis Star, Stan Smith ranked World’s 1st, Adidas contacted him with a unique proposition to design a Tennis shoe.

This deal marked one of the most influential sponsorships in sporting history and in doing-so made one of the chicest and coolest men’s trainers designs of all time.

Available in minimalist White with Green accents, the Adidas Stan Smith is a favourite amongst men’s style icons and fashion bloggers alike.

Adidas Stan Smith

New Balance 576

There’s something about a retro inspired men’s trainers design which never fails to excite me. When New Balance released the sleeker New Balance 576 in 1988, only the coolest kids in school wore them.

When this classic, cool men’s trainer design was re-issued in 1996, a more modern colour-palette introduced new life and new fans to the timeless men’s trainer.

Today, New Balance are still celebrating major international success with their kitsch line of running trainers. New Balance are the ultimate comfort shoe for those who need to run about town with a little edge.

New Balance 576

Nike Air Max

Originally released in 1987, the Nike Air Max was a baffling men’s trainer design idea for many. Using ‘Air Cushioning’ in the sole of the sports shoe, to distribute weight and support the foot, the Nike Air Max can be identified by the unique air bubble, exposed on the outside of the trainer.

With over 60 re-issues of the original Nike Air Max design, the Nike Air Max style has gone on to become one of the highest-selling, cool men’s trainers of all time. We favour the cleaner, more sophisticated model – the Nike Air Max 90, available in a range of modest and bold colour-ways to suit every man’s style.

Nike Air Max

Vans Old Skool

The iconic, California Skate and Surf brand, Vans, recently celebrated 50 years of success. Vans Authentic, Vans Era, Vans Classic Slip-On and the Vans Skate-Hi are amongst the favourable styles worn by famous hipsters from Stacey Peralta to Sean Penn on Vans’ rise to the top.

Vans trainer design #36 gained a real cult following with stylish men and trend-setters. The Vans Old Skool is one of the original takes on a contemporary skate-boarding shoe. Designed with leather panels and a waffle sole for additional durability, the Vans Old Skool is THE versatile go-to for every guy. As one of the most versatile and coolest Men’s Trainers, we suggest you buy in Black & White and wear with just about everything!

Vans Old Skool

Reebok Classic

As a basic men’s trainer with very little to set it apart from some other the other iconic men’s trainer designs and contemporary sports shoes – the Reebok Classic has managed to stand the test of time.

Designed on the wave of the fitness and aerobic movement, in the early eighties, the Reebok Classic is marketed as retro sports shoe for running and basketball. Celebrities and Style Gurus love it and we have to commend the Reebok Classic for what it is – a cool, cult trainer for men with the simplicity to team with everything from high-street to high-fashion.

Reebok Classic

Adidas Superstar

Okay, so Adidas have taken another spot in ‘7 of the coolest men’s trainers of all time’ but there’s no denying that, Adidas are the Kings of Sneakers with cool mens trainers design innovations which inspire generation after generation of men.

The Adidas Superstar was launched in 1969 as a variation on a volleyball shoe. When rap trio RUN DMC adopted the shoe as part of their stage-dress in 1983, Adidas jumped on it and the Adidas Superstar we know today, was officially born.

The Adidas Superstar Men’s trainer or the ‘Shell toe’ remain one of Adidas’ most famous designs, cementing an affinity with Rap culture and music. If you’re looking to invest in an Iconic Trainer to up your game…just walk this way!

Adidas Superstar

So, there was have the ‘The 7 Coolest Men’s Trainers of All Time’ Do you own any of these classic mens Sports Shoes? Or have I missed out some men’s trainer designs that definitely should have made the list?

If you’re a ‘sneakerhead’ we’d love to hear from you and have your input. Be sure to follow us on Facebook and Instagram for fashion updates and news from the World’s style influencers.