Best retro sneakers 2021: big ugly shoes

Retro sneakers are all the rage at the moment, and these are top of the pile

Best retro sneakers

Retro-styles are the only sneakers to be seen in now (and probably next year too), from flashy and hi-tech Nike Air Max to understated Adidas Stan Smiths.

The most fashionable styles originate from the 1990s. This was the era when sneakers started to flaunt their technical credentials, from the neon flash of the Adidas torsion beam to the ever larger Nike air bubbles. 

To score extra fashion points, opt for styles that are ugly. You can thank Balenciaga for starting this unusual trend, which seems to be inspired by those white Nikes worn by all American men of a certain age who have begun to value comfort and value over style.

From the ugliest of sneakers to the elegant premium versions of classic styles, here are our favourite retro trainers.

1. Adidas Originals Stan Smiths Leather Sneakers

The trainer to complete almost any outfit

Reasons to buy
+Minimal design complements most outfits+Off white colour adds new retro appeal
Reasons to avoid
-Fairly common-Difficult to keep clean

Adidas’ Stan Smith is a subtle design that whispers retro rather than screams it and has become a staple of the retro trainer trend in recent years. Versatile, affordable and comfy, it is easy to see why this shoe is so popular. 

This version features a new off-white colourway that nods towards the ugly trainer phenomena, but unlike some of the more outlandish expressions of that trend, the Stan Smiths will still fit into most wardrobes. The only risk you will be taking in these norm-core favourites is blending into the crowd a bit too much. 

The £85 price tag may seem a lot for a basic trainer, but you’ll be quids in in terms of cost per wear, as these shoes go with everything.

2. Nike Air Max 1 Premium Suede Sneakers

Luxury version of a technical sportswear classic

Reasons to buy
+Suede finish dresses up the trainer+Iconic air bubble still looks cool
Reasons to avoid
-Suede is harder to clean than leather-Re-issued design has been around for a while now

This trainer revamps the design that introduced Nike’s iconic visible air bubble in 1987. While you may have had a pair with pops of bright colours in the 90s, the style’s been given a premium makeover in sophisticated moss green suede. 

The use of the tactile material elevates this trainer to a smarter proposition so you might even get away with wearing them with smarter outfits than you would usually dare.These wouldn’t look too amiss worn with a shirt to a club. You could even try them on at work, depending on how relaxed your boss is (and whether your office already features a football table and bean bags.) 

Moss green is an easily wearable and attractive colour paired with denim and the warm, rusty colours of this season. The shoes come in at £105, which is an attractive price considering the premium finish.

3. Nike Air Skylon II Sneakers

Lightweight sneaker with a heavily retro design

Reasons to buy
+Ticks a lot of trend boxes+Bargain price is also a throwback to the past
Reasons to avoid
-Neon colours are harder to pair

Nike has dig this known design out of its 1992 archives to give it a new lease of life. Clashing pure white with off white is a full on expression of the ugly trainer trend and the neon fade inset nods to vapourwave. 

This shoe certainly captures the footwear zeitgeist. But think carefully… how many clothes do you own that will look good with white, off white, neon red and neon yellow all at once? If the answer is none, then move on. If the answer is who cares - clashing is the whole point - then these might just be your next sneakers…and they would look great with pretty much any denim if you’re feeling lazy. 

The relatively small £85 price tag adds to the temptation and it is a bonus that lightweight mesh construction and foam and air soles ensure standard Nike levels of comfort.

4. Adidas Originals Yung 1 Nubuck and Mesh Sneakers

The original ‘Falcon Dorfs’

Reasons to buy
+On trend 90s aesthetic+Modern tech adds comfort
Reasons to avoid
-Not quite as inspired as Nike’s efforts

There is something a tad confusing about Adidas’s current line-up of 90s inspired trainers. First, there’s the Falcon Dorfs, which are a re-issue of a trainer that first dropped in 1997, except that the re-issue doesn’t actually look like the original. Then there’s these, which are not officially a re-issue, but which appear to be identical to those original Falcon Dorfs of ’97.

Whether that’s a good thing will be in the eye of the beholder, because the Falcon Dorf was one of the true ugly trainers of the 90s and surely one of the inspirations for the current crop of high fashion imitations. The off white, navy and forest green colour-way is quintessentially 1997, but not in a particularly cool way – you would probably have seen them in an expensive squash club rather than in the DJ booth at a house night – but maybe that adds to their current appeal. 

This is the shoe for anyone who wants to invest in 90s nostalgia but also wants to pass on the more excessive colour schemes of that era.

5. Nike Air Max 95 Panelled Faux Suede and Mesh Sneakers

A 90s classic in colours only 2018 could produce

Reasons to buy
+Guaranteed to turn heads+Design is beautiful and not just retro
Reasons to avoid
-Off the wall colours could get old quickly

Some trainer designs seem to have been brought back just to satisfy the current insatiable appetite for all things 90s, regardless of whether they were any good at the time. The Air Max 95s on the other hand have always been a beautiful design and are likely to endure in popularity even after the current 90s mania has fizzled out like the comedown from a rave.  

You might just feel like you’ve taken something when you first clock eyes on the colour scheme of these particular re-issues. It must have taken some vision to see that concrete effect soles and red air bubbles would combine well with white, pink, navy and orange uppers, but it does work. 

It is also refreshing to see a sneaker that references the 90s but also adds something that the original designers would never had thought of.

6. Converse Chuck 70 OX Suede Sneakers

The latest iteration of THE retro trainer

Reasons to buy
+Timeless design+Look better with jeans than running shoes do
Reasons to avoid
-Plimsolls have never been so expensive

You couldn’t have a rundown of retro trainers without including Converse. They might not be the at the pinnacle of cool at the moment, having had their moment a few years back, but they deserve an entry for their sheer endurance. Chuck Taylors have been much the same since the 1920s. 

The 90s is not the only trend going on at the moment, and these burgundy suede versions will work well with the more faded, warm, 1970s inspired look that is also popular. They would look great next to stonewash denim and some tasselled brown suede, and could be a comfier and less try-hard alternative to the cowboy boots that would usually complete that look. 

It might be hard for some to part with the £75 for a pair of plimsolls, especially anyone vintage enough themselves to remember the near pocket money sums a pair of Chuck Taylors used to sell for. But unlike the classic canvas pairs, these will keep your feet warm and dry this winter – worth the investment if you ask us.

7. Raf Simons + Adidas Originals Ozweego Mesh and Leather Sneakers

The original high end ugly trainer

Reasons to buy
+Creative use of colour+Boasting rights as the original ugly trainer
Reasons to avoid
-Pink soles will look dirty quickly

Raf Simons and Adidas could claim to have created the ugly trainer fad by releasing the first version of these Ozweego shoes back in 2013, long before it was cool. The two-tone colour scheme is visually clean and refreshing amongst the melee of crazy 90s designs out there at the moment. 

Continuing the pink colour of the uppers all the way over the soles is a clever trick that keeps the overall visual effect super minimal. It will come at a cost though, as those soles will never stay pink. 

If you are someone whose chauffeur driven Bentley takes you right up to the door of Harvey Nicks (and the £330 price tag is a snip) then these would be an extremely stylish wardrobe investment. But they would be wasted treading the pavements for the rest of us.

8. New Balance 998 Suede and Mesh Sneakers

The New Balance Sneakers that no-one else has

Reasons to buy
+Modern updates for comfort+Made in USA label
Reasons to avoid
-High quality commands a high price

New Balance is a company whose comeback in street fashion has been entirely fuelled by our appetite for retro. They were well poised to take advantage of the trend with a back catalogue of elegant designs from the 1970s and 80s, always in their trademark suede. Their 574 model has become a ubiquitous sight. 

Although still a great design, the sheer popularity of that shoe has caused it to lose its edge a bit. Plump for this 998 though and there is far less risk of finding yourself stood on a train platform between two people in the same shoes. There is a price to pay though for separating yourself from the masses, and that price is £190. 

You might wonder how the label with the big N justify this. For one these sneakers are made in the USA, and how often do you see that label on a trainer? They were also New Balance’s flagship running shoe when released in the early 80s, commanding a high price even then. And now they have been brought even further up to date with ABZORB sole cushioning borrowed from NB’s latest runners.

9. Fila Disruptor II Trainers

The trainer with its own hashtag

Reasons to buy
+The trainer of 2018+White will pair easily
Reasons to avoid
-Don’t expect to be taken too seriously-Good luck finding your size in stock

You can’t think of Fila without thinking of the 90s. The entire brand is a throwback, and because it became synonymous with more excessive side of sportswear back then (think full matching tracksuits and a lot of gold) it will forevermore be worn with irony.  

With the 90s being current reference decade du jour, Fila was bound to blow up, and no other shoe in its range has taken off quite like the Disruptor. The hashtag #filadisruptor has hit 175k posts on Instagram and the shoe has become a phenomenon on social media. 

As a result, you might struggle to track a pair down in your size. If you want to hop on the Disruptor bandwagon, you’d better start scouring the internet for a pair soon, as it’s only so long before we reach peak Fila. You have to give the brand credit though for keeping the price at an affordable £80 despite all the internet hype driven demand. 

10. Vans Old Skool Brown Suede Trainers

Luxury topped waffle

Reasons to buy
+Waffle soles are useful if you skate or cycle+Ochre colour is very now
Reasons to avoid
-Not the most comfy soles for walking

A retro sneaker list wouldn’t be complete without a look in from Vans. If your feet spend a lot of time planted on the deck of a skateboard or the pedals of a bike then none of the squishy soled running sneaks making up the rest of this list will be any good… you need a pair of Vans. 

The skate brand’s trademark waffle soles have been providing grip to skaters and riders for generations. Some designs just don’t need to be altered, and the Vans Old Skool is not selling strongly in 2018 because it fits the retro box, but because it works. This style is the latest iteration of the brand’s classic skate shoe which debuted in 1977. 

It features all the emblems you expect from a pair of Vans: white side stripe - check, red tab on the heel - check, tan waffle soles - check. Suede upper panels give these a luxe finish and the ochre colour is bang on trend. The high end finish does effect the price, and £75 is top whack for a pair of Vans. But if you do skate, you could see these as ticking boxes for both function and fashion.