There are countless varieties of sneaker and it can be particularly hard to not only choose when to wear them but the right ones for the occasion. After all, some sneakers are more casual than others despite being a very casual class of shoe!
In this guide, you’ll learn everything there is to know about sneakers as well as the best ones to buy online:
You can click on one of the links above to jump ahead to a particular section, or continue below to read the entire article from start to finish.
Quick Buyer’s Guide
Just looking for a quality pair of sneakers? Use the Quick Buy guide to head straight to the retailers. Alternatively, scroll down to discover each one and read more about the style.
See All Bespoke Unit Shoe Style Guides
What Are Sneakers?
At their core, sneakers are simply soft shoes with rubber soles made for very casual or athletic endeavors. Referred to as “trainers” in the U.K., no man’s wardrobe is complete without them, even if that man wears a suit and tie five days a week.
Currently our favourite casual sneakers that you can buy, Beckett Simonon’s footwear is ethically handmade from Argentinian calfskin leather in their Colombian workshop. There are several black and white options available in either full-grain or suede leather.
Crafted from Italian calfskin leather, these high-quality sneakers are made using a side-stitched construction technique. Handmade in the same Colombian workshop, Beckett Simonon’s Reid sneakers are another great example from the brand.
You can also benefit from a 20% discount with our exclusive code “BU20” during checkout!
An undeniable classic, the celebrated Stan Smith range from Adidas represents the quintessential casual sneaker that can also be worn as sportswear. Despite arguably being one of the shoes that started it all, it hasn’t aged for the contemporary man.
Also Featured In
Indeed, these aren’t your typical casual sneakers. In fact, many might argue that is definitely not one to wear casually. However, if you’re fond of the great outdoors and live in an area with rough terrain, they’re a great choice. In fact, they’re what our editor wears when walking his dogs!
Also Featured In
Comfortable and versatile yet oh-so stylish, the Skechers Go Walk 4 is a great urban sneaker to wear when out and about. They’re stylish enough to wear for your daily errands but also perfectly adequate for light sporting activities.
Also Featured In
We couldn’t end without having covered a pair of Nike sneakers and their unmistakable Swoosh ticks! The Winflo 5 is our current favourite. Not only does it feature an attractive design but it’s built for both comfort and stability.
How To Wear Sneakers
We love us some fancy dress shoes, we really do. Our closets are filled with monkstraps, oxfords, and chelsea boots in all manner of leathers and suedes. We love to dress to the nines, as it makes us feel powerful, strong, and handsome.
Man cannot live only in leather soles, however, and sneakers are an indispensable part of every man’s wardrobe.
Sometimes you just need to throw on some sneakers and be done with it. Anyone reading this who has ever been dragged to a diner while hung over at 10am can cosign, surely. Those of us who have children to stroll about with on the weekends will understand this, and even the dog owners amongst us know that while it’s cool to look amazing in double monks while walking your pup, it’s a lot more comfortable in a pair of sneakers.
Athletic Sneakers Versus Sporty Sneakers
Don’t get it twisted: we are not talking about athletic sneakers here. Sure, there’s a time and a place for those: exercise time, and wherever your exercise place is. That could be the gym, the track, wherever you rock climb, or wherever you engage in a physical activity that physicians refer to as “exercise.”
Out at brunch, though? Running errands downtown? You don’t want to wear athletic sneakers unless you are so far out of shape that eating pancakes and mimosas at noon counts as “exercise.”
Don’t be that guy walking around in Dad jeans, a tucked in polo shirt, and cross-trainers. These are not at all stylish, and all they tell the world is that you don’t care if you look ridiculous. Aesthetically, you might as well tuxedo shoes with the same outfit since it makes an equal amount of sartorial sense.
For those of us more concerned with looking “sporty” as opposed to engaging in actual sports, a simple non-athletic sneaker is best. Pro tip: you may see these advertised as “lifestyle” sneakers.
Slipons, Laces, Straps, & More
While prototypical sneakers had laces, various forms have evolved over the last century. You can now find sneakers in lace-up versions, slip-on styles, and even with velcro straps. Even double monkstrap sneakers have seen a surge in popularity!
Velcro straps tend to be very popular with young children who don’t know how to tie laces yet, and it’s our understanding that the sound of velcro being pulled apart is the bane of many a kindergarten teacher’s existence. Still, they style is available for adults from various makers.
Different Styles Of Sneaker
Converse All-Star (The Chuck Taylor) & Jack Purcells
The Chuck Taylor has a long, rich history. It was actually the first basketball shoe, so its roots are indeed as an athletic sneaker. It has crossed over into mainstream casual wear, however, as basketball sneakers nowadays bear almost no resemblance to the Chuck Taylor.
In 1906 in Malden, Massachusetts (a suburb of Boston), a gentleman named Marquis Mills Converse created a company: the Converse Rubber Shoe Company. His company designed the “Non-Skid” model in 1917, which was the forerunner to the All-Star we all know. With a non-skid rubber sole and a canvas upper, it was designed to be a basketball shoe.
In 1923, a basketball player named Charles (ahem, Chuck) Taylor joined a basketball team sponsored by the Converse company. This team was called the (ahem) Converse All-Stars. Taylor led basketball clinics in high schools nationwide, selling the shoes while doing so.
By the 1960’s, about 90% of American collegiate and professional basketball players wore Converse All-Stars. Soldiers in World War II wore them in basic training. Olympic athletes at the time wore them. They were ubiquitous.
While no longer worn on the basketball court, Chuck Taylors have become extremely popular with rock musicians, artists, and skateboarders. As they’re relatively inexpensive, available in high- and low-top versions, and made in every color and material under the sun, they’re easy to acquire and have a place in any gent’s wardrobe.
The Jack Purcell is a very similar model (basically the same thing but with a color block strip at the toe), perhaps most famously worn by Elvis Presley and Kurt Cobain.
Adidas Stan Smith
Another sneaker that started off as athletic but transitioned to casual wear, the Stan Smith was a tennis shoe before anything else.
Adidas originally designed this shoe back in the early 1960’s, making it the first-ever leather tennis shoe. One of the only Adidas lines to not feature three diagonal stripes on the sneaker’s side, it instead uses rows of perforations. A green pad was later added to the back to protect the Achilles tendon.
Originally named the Adidas Robert Haillet after the French tennis pro, the name was changed to the Adidas Stan Smith in 1971. Stan Smith was an American tennis champion at the time, and the partnership allowed Adidas to break into the American market while garnering Smith royalties for the use of his name.
This is absolutely, hands-down, without a doubt Paul’s favorite sneaker. Without exaggeration, he must have at least twenty pairs, and it’s easy to see why. The design is simple, so it’s versatile and never goes out of style. The color way options are very extensive, so you can always find something new and fun. Perhaps most importantly, they’re comfortable and available in a wide range of sizes, specifically Paul’s 14 wide!
This silhouette doesn’t really have a name, but it’s essentially a catch-all sneaker shape that any guy can use in his closet. It’s comfortable, slim, and is made by a number of different sneaker manufacturers.
These sneakers are often found nowadays with details you’d typically see on dress shoes: broguing, monkstraps, cap-toes, and the like.
You can’t talk about sneakers without talking about sneakerheads.
“Sneakerhead” is a term that refers to anyone who collects sneakers. These are the guys who’ll line up for hours outside retail stores whenever the next Air Jordan (or whatever the model in question is) is released, and it’s almost as if money is no object to them, they just want the sneaker. There’s definitely a cult following for certani brands like Jordans, and sneakerheads are the cult members.
We respect the practice. Buy the things you love and cherish them. #yolo, right?!?
How To Wear Trainers
It doesn’t get much more casual than a pair of sneakers. With that said, they can be dressed up to an extent. Below, we offer some suggestions for what trousers to pair with sneakers.
- Jeans: canvas, leather, or suede sneakers in any color
- Shorts: canvas sneakers in any color
- Casual chinos: canvas, leather or suede sneakers in any color
Sneakers & Suits?
The practice of wearing sneakers with suits has been flirted with since the early 2000’s. Proponents will say that so long as the sneaker isn’t bulky and that it’s all one color (typically white), then you’re good. Opponents say that suits require dress shoes, and sneakers simply don’t make the cut.
Generally speaking we agree with the latter, not the former. It’s one thing to mix high and low, but quite another to wear a sartorial oxymoron. If you want to look casual, you should consider perhaps not wearing a suit.
An exception we can make is for beach weddings or other such events where the groom is a very casually dressed guy who needs to wear a suit for the day. A white All-Star with a khaki or linen suit is common. Even so, we make this exception with a hint of reluctance.
Sneakers can be worn any time of year. We’re happy to offer some suggestions below, but know that the world is really your oyster in a pair of sneakers and there are many more places to go than what we’ve listed here:
- Spring: Canvas high-tops in light colors (blue, beige, tan, etc.)
- Summer: Canvas low-tops in white or bright colors
- Autumn: Leather or suede slip-ons in tan or navy
- Winter: Leather or suede lace-ups in black or brown
Should I Buy Sneakers?
Absolutely! Any man, regardless of his day-to-day dress code, should have at least one pair. The beauty of them is that the classic ones are still quite inexpensive, so you can pick yourself up a couple of different colors to round out your collection.
The short answer: a resounding yes.
Now that you have learned about sneakers, check out some our related footwear guides for men:
- Top Boat Shoes For Men
- Best Casual Summer Shoes For Men
- Best Running Shoes For Men
- Men’s Shoes Homepage
"A great selection of casual sneakers. I love the sneakers by Beckett Simonon. Now I need to decide which ones I prefer!"Rating: 5.0 ★★★★★