How To Wear Sneakers & Look Damn Fine At Every Occasion

Once a shoe reserved for running is no more...

In case you’ve been living under a rock, your sneakers are meant for more than just the gym these days. Though they got their start as flimsy ‘plimsolls’ meant for working-class holidaymakers and purpose-built footwear designed for athletes, sneakers have become a staple in every man’s (and woman’s, for that matter) wardrobe. From lifestyle to the red carpet to sports, nowadays your sneakers can be an expression of yourself. And today we’re showing you how to do it right.

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Basic Sneaker Rules

No matter what kind of sneakers you settle on, there are a few basic principles for how to wear sneakers.

Always:

  • Buy sneakers that suit your current wardrobe: What good does it do to buy the latest ‘hype’ style if it doesn’t suit your style? Don’t hop on the trend train just because it’s passing through. Choose shoes that complement what you already have, not shoes that require you to repurchase your entire wardrobe. We’re looking at you, Yeezy lovers.
  • Wear them to the right occasions (don’t go too casual): Sneakers are incredibly versatile, but they’re no substitute for dress shoes. You can get away with sneakers with any off-duty outfit – and perhaps even some casual, unstructured suits – but they’re not meant for every occasion (i.e. weddings). Err on the side of overdressed rather than underdressed.
  • Keep them clean: It doesn’t matter how cool your sneakers are, the effect will be lost if they’re not spick-and-span. Proper sneaker maintenance includes washing the laces, eliminating odours, brushing the outsoles, and using shoe trees and sneaker shields.

Understanding Your Sneakers & Trainer Types

Sneakers come in many shapes and sizes these days. From basic unstructured canvas to the brightest, finest leather; from minimalist looks to metal fastenings and high technology; there are few rules when it comes to trainers. With so many options available, it can be hard knowing exactly what’s what and even harder to know what’s most likely to suit your wardrobe and taste.

Luckily, you have us here to make things easier. We’ve put together a How To Wear Sneakers Style 101 guide that should have you acing your footwear exams in no time.

  • Basic Sneakers – These are your Converse, Vans, etc., types. Sometimes they come in leather, but they’re typically found in canvas and in basic colours. On the whole they’re generally affordable, easy to wear / clean, and work well with just about anything. They might not be the most comfortable, however.
  • Refined Luxury Sneakers – They might bear a resemblance to your basic plimsolls, but they’re more expensive and often made from suede or leather by brands like Tom Ford, Lanvin & Saint Laurent. These are not something you’d take to a music festival.
  • Classic Sports Sneakers – Your Nike Air Max, Reebok Pump, Asics Gel-Lyte and other forms of old school sporting greatness. What was once ready for the track and field is now kept safely in a shoe collection at home.
  • Modern Sport Sneakers – Again, these are your Nike, Adidas and Puma-tier brands, but with modern styling and shapes. As a rule, it’s harder to pull off modern sports sneakers than it is to pull off classic styles.
  • Hiking / Trail Sneakers – As the name implies, these shoes were designed with technical activities in mind, but are fast finding a place in mainstream fashion. Think Salomon, La Sportiva or Keen. Not the easiest to style.
  • High-fashion Sneakers – These are the work of brands like Givenchy, Christian Louboutin, Maison Martin Margiela, Diemme and even Giuseppe Zanotti. They’re loud and designed to be noticed.
  • Luxury Techwear – This is the category for the likes of Rick Owens, A-COLD-WALL* and other designers who are really pushing the limits of sneaker design. Blending technical sneakers, high fashion as well as their own unique aesthetic, these are real statement pieces.

SHOP: The Best White Sneakers To Buy

Get The Best Sneaker Look

Now that you’ve selected your poison, it’s time to actually pair them with your wardrobe. And no, it’s not a case of wearing your one pair of sneakers with any pair of jeans. There’s a fine art in the craft so pay attention.

The Basic Classics

Lows, Chucks, canvas kicks… whatever you call them, the basic sneaker is the most versatile casual sneaker you can buy. They work well with denim, chinos and shorts of pretty much any colour and shade.

Where we find guys sometimes get a little unstuck with these types of sneakers is when they wear them to smart casual events or to work when a dress shoe is required. The basic sneaker DOES NOT work for every occasion and should be kept solely for casual situations. Your best bet on top is to run with print t-shirts, gingham shirts or even a blazer for the college professor look.

  • Mix with relaxed, slim & skinny denim and chinos
  • Keep for casual/street occasions only
  • Maintain to ensure they stay clean and respectable
  • Best suited to younger men

Luxury Sneakers

Our personal favourite is the luxury take on the basic sneaker. These beautiful specimens have allowed sneakers to jump from street casual to smart casual without looking like they belong on a teenage boy. They can be worn with tailored trousers, slim denim, chinos and in some cases even casual unstructured suiting.

Avoid wearing them with shorts, as these sneakers are quite often bulky in comparison to the basic canvas sneakers. Keep it refined on top to match the shoe. Basic t-shirts, smart shirts and polos are all great options. For a more distinct look, opt for a shirt with a slim or knit tie, a blazer and some slim denim.

  • Dress up, not down
  • Start with black, then purchase other colours
  • Take extra care with suede and don’t wear it too often
  • Try brighter pairs for summer / European holidays

Classic Sports Sneakers

Sneakerheads, unite! These babies started the sneaker revolution that we have today. Jordans, Superstars, 95s – these are your street-going, on-trend kicks that are just popping with colour. The idea with classic sports sneakers is to find a couple that complements your style and purchase a few pairs in different colours.

Slim- and tapered-fit denim, loose t-shirts (with or without prints) and casual outerwear are your essential staples when it comes to dressing these sneakers. Pair them with chino shorts for an easy win in summer. The key is to find the balance between hip-hop artist and everyday citizen. Some guys like to rock a snapback – that’s up to you. Personally, we like to colour match our sneakers with what we’re wearing on top, to give the look a sense of purpose and cohesiveness.

  • Find a few styles you like and stick to them
  • Colour match if you can
  • Pin roll, or rock with khaki chinos when it’s warm
  • Sell them on eBay if you don’t like them

Modern Sport Sneakers

Wearing this style of sneaker can have you looking like Jerry Seinfeld if you’re not careful. On the other hand, you can quite easily look like a ‘houso’ if you pair them with tracksuit pants. As much as possible, stick with sneaker releases that are low profile with a fashionable edge.

Too runnery/sporty and they’ll look bulky and not quite right. Wear these as you would classic sneakers or with gym/running gear on the weekend. Steer clear of denim that’s loose-fitting, as it never seems to work. Instead, choose slim Nudie chinos or elastic cuff variations. On top, keep it sporty and casual with t-shirts only.

  • Avoid all white pairs running trainers… eeew!
  • Don’t tuck shirts into denim with these sneakers
  • Go for a sporty look to complement the shoe

Designer Sneakers

Expensive and not for the faint of heart, these top-end sneakers are getting louder and more in-your-face every season. For an example of someone who wears them well consistently, look to Kanye West. A common approach to wearing these sneakers matches them with slim denim that’s often gathered at the bottom and t-shirts with open plaid shirts. There’s also the Parisian style, which includes long and drapey blazers and singlets that add even more edge to the look. Black denim is a must-own item as well as longer, looser fit t-shirts.

  • Stick with blacks, whites and muted colours
  • Let the sneakers to the talking
  • Denim is your best friend

High Tech Sneakers

Only a few will dare to wear these sneakers. They’re highly fashion-forward and to me only really work with drapey and long fitting clothing. Stick with black and do as little as possible to draw attention to the shoes – they will do that themselves. Ideally, you want people to think that you’re not trying too hard when you wear these types of kicks, so muted attire is best.

  • Black, black, and more black
  • Go for long and draped style of clothing
  • Be prepared for people’s comments

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