How To Wear Retro Trainers

by Welcome to Outsons

It’s safe to say that retro trainers have certainly made a comeback in recent seasons and now are the biggest trend in the sneaker industry. Below we have shown you which ones you need to get your hands on. 


When you think of retro trainers you are probably taken back to your childhood. Brands such as Kappa, Fila, Adidas and Nike will most likely stand out to you and you are more than likely filled with nostalgia. Well, luckily enough for you the trend is very much back on top and we have seen a revival in the chunky silhouettes of the Nineties, as well as a resurgence in the popularity of certain shoes.

Below we have shown the shoes which are more popular now than ever before, and you need to get your hands on if you really want to nail the vintage trainers trend. We have shown you how to wear these with ease.

How To Wear Retro Trainers

Go Smart-Casual

If you’re planning on wearing retro trainers to work (if your office or workplace allows trainers, of course) then the best thing for you to do is go smart-casual. Pair a classic and crisp white style like Reebok Classics or Adidas Stan Smiths with a pair of smart chinos and a shirt for the ultimate smart-casual look. For the office, we always suggest that if you are going to try and wear trainers, please make sure they are clean as you are still there to make an impression and impress your boss. Alternatively you could go down the jeans and blazer look, again, if your workplace allows jeans.

For a day-to-day look for when you’re off work, try wearing a pair of tapered or slim fitting wool trousers with a turtle neck and a pair of retro trainers. Nike Air Force One has made a considerable comeback in recent years and appear to be standing the test of time, so we recommend getting your hands on a pair of these if you want a pair of trainers which will not be going anywhere anytime soon. Since 1982, they have been one of Nike’s leading trainers and little has actually changed to the original shoe. The Air Force One is such a solid trainer that it can almost be pulled off with a more smart outfit.

smart casual retro trainers look men-min

Wear with a Suit

Retro trainers will go perfectly with a suit if you do it properly and go for trainers that are still quite smart. As we have said above, Nike Air Force One (when clean) fit the bill. Other trainers that would be suitable are Puma Suedes or Converse Chuck Taylors. Both of these will be suitable with a suit of any colour, going particularly well with a navy or grey suit.

We recommend wearing a slim fitting suit if you are going to wear one with retro trainers, and if possible you should try and go for a pair of cropped trousers to really show off your kicks.

Wear with a Tracksuit

For the ultimate retro look you could go for the full tracksuit. The likes of Burberry and Gucci have been repping this on the catwalk. The best thing to do is go for an all-in-one matching tracksuit and pair with a pair of chunky trainers, like Nike Air Force One or Reebok Workout. Where once upon a time a full tracksuit was deemed the look off hooligans, nowadays it is more than acceptable and will give your retro trainers a finishing touch.

Wear with Skinny Jeans

The thing with a lot of retro sports trainers is that they are actually pretty thin. We don’t mean thin with respect to the material, but we mean that compared to a lot of the chunky trainers of today, a lot of them were fairly streamlined.

As a result of this, we recommend that you stick to skinny jeans when wearing the likes of Onitsuku Tigers and Nike Cortez, because although we are all for wide legged trousers, they just won’t look right. The wide hems of baggier trousers don’t sit well with smaller more lightweight trainers and will leave your feet looking smaller than they actually are.

Wear with Dickies

If you do want to wear retro trainers like Vans SK8 Hi or Vans Old Skool then we do think these go best with Dickies or other free flowing chinos. In particular, Vans go well with Dickies 874 chinos as these are the baggiest and are best when trying to achieve that Nineties skater vibe. These retro indie trainers are a favourite by almost everyone and we cannot see them losing their popularity any time soon.

To this day, the 874 Dickies pants for men are among the brand’s best-selling products, and it’s no wonder why. The original 874 work pants come with all the practicalities you would expect from the brand, including wrinkle resistance and stain release, making them ideal for an everyday pair of trousers that’ll stand the test of time.

mens street style dickies vans

Vans is one of the most recognisable trainer brands on the planet, and you can really achieve that retro feel by investing in a pair. Vans Old Skool are the most popular and are an extremely versatile pair of shoes, with just the right amount of a retro edge. We would even go as far as saying that you could wear these to work with a suit if you did it right (we’d stick to a black and white iteration of them for this though). Vans SK8 Hi are a little more out there and we wouldn’t suggest even attempting to wear these in a formal environment. Instead, keep these for casual days and do as aforementioned – pair with Dickies for that skater look.

How To Wear Retro Trainers

  • Smart-casual – team a pair of crisp white retro Reebok Classics or Adidas Stan Smiths with smart trousers and a shirt for a smart casual look that is even wearable to the office.
  • With a suit – go for a pair of Adidas Stan Smiths or Converse Chuck Taylors if you want to wear a suit with a pair of retro trainers. Make sure they are clean.
  • With a tracksuit – if you want to go for full Nineties retro look then this is the way to do it – a full tracksuit a la Gucci with a pair of chunky trainers from the likes of Reebok or a pair of Nike Air Force One.
  • With skinny jeansretro trainers like Onitsuka Tigers and Nike Cortez tend to have a slimmer silhouette and so you should avoid baggy trousers as these will make your feet appear smaller than they probably actually are.
  • With Dickies – if you want to go down the retro skate route with a pair of Vans Sk8 Hi or Vans Old Skool then we recommend getting yourself a pair of Dickies.

stan smith retro trainers mens

On That Note

Wearing retro trainers has become the norm, as brands like Nike and Reebok have really pushed trainers such as the Air Force One and the Reebok Workout amidst a revival and resurgence in popularity of the Nineties style. Above we have outlined the ways that we think you can wear retro trainers, depending on which ones you go for, from pairing Converse Chuck Taylors with a suit to pairing Vans Sk8 Hi trainers with Dickies. We have gone through the ways in which you can wear the best retro trainers for men.

Feature image from Pinterest

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