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6 shoes every man should own and the interesting history behind them

We’re getting back to basics today to talk footwear essentials. There are some shoe styles that every guy should have, whether for their longevity, their versatility, or their place in current culture. 

From dress shoes to sneakers, these shoes all have rich histories that prove they'll always be a mainstay. Having them in your wardrobe will help you avoid falling into a pattern with your footwear and allow you to mix things up a bit. Suits and sneakers, oxfords and jeans--with these six styles you'll never find yourself reaching for the same pair of shoes every day again. 

A quick note: There are lots of footwear rules out there, but we subscribe to the philosophy that anything worn with the right amount of confidence will always look good.

1. Oxfords - Rooted in Rebellion

Sometimes referred to as: Balmorals

Oxford shoes

Wholecut oxfords

The characteristics of oxfords: 

Oxford shoes are sleek, clean, and characterized by their closed lacing system, low heel, and exposed ankle. They sit at the very top of the ladder of formality. This is a style of shoe you should invest in because you will always need a pair. 

You’ll see a couple of different variations of oxfords out there. A whole-cut oxford is one that is made from a single piece of leather. You won’t see any seams, perforations, or other details. It’s sleek, and it is the most formal of all shoe designs. 

Colin Firth in kinsmen in front of wall of Oxford shoes

Colin Firth's character in Kingsmen explaining the importance of oxfords.

You are also likely to see saddle oxfords, two-toned oxfords, and other details like broguing that give them a sportier, more preppy look. But as Colin Firth’s character in Kingsman said, “Oxfords, not brogues.” Stick with the basics and you can’t go wrong. 

The History of Oxfords

Oxford shoes hail from… wait for it… Oxford University in England. What you may not know is that they have a history of rebellion. Even the origin itself is somewhat contentious. Both England and Scotland/Ireland claim shoe style as their own, though the Scottish/Irish version is referred to exclusively as Balmorals, while the English distinguish Balmorals as a specific style of oxfords.

The story of English oxfords goes that students at Oxford University were tired of the uncomfortable heeled boots they had to wear, thanks to King Louis the XIV who popularized them due to his short stature.

The students began wearing Oxonian shoes in the 1820s, which was more like a half-boot with a lower heel and side slits. Eventually they evolved into the ankle-exposing oxford we know today. Racy! 

In the early 1900s, oxfords crossed the pond and became a common look in American business attire. The 1920s saw women embracing the shoe style as they began wearing men’s clothing as an act of rebellion to oppressive societal norms. 

Tips for wearing oxfords

Patent black leather oxfords with a plain toe are the most formal shoe around and should be reserved for black-tie occasions. They should always be straight-laced rather than crisscrossed. Other than those basic rules, feel free to experiment a bit with how you’re wearing yours. 

Dark grey oxfords with brogue details

Try wearing classic brown oxfords with cuffed chinos and no-show socks for a preppy summer look. Or wear them with dark jeans and knitwear for a smart casual look. Keep in mind that lighter coloured leather, suede, rubber soles, and brogue details are all casual touches that will automatically dress them down.

2. Derbies - The Ass-Kickers

Sometimes referred to as: Bluchers

Derby shoes

Brown derbies with brogue details

The characteristics of derbies

Derby shoes are similar in structure to Oxfords but for one defining characteristic: the open lacing system, where the two quarters (the back pieces of leather) and eyelet tabs are sewn on top of the vamp. This detail makes them slightly less formal than Oxfords, but still completely appropriate for business and nearly any event. 

The terms "blucher" and "derby" are often used interchangeably, but TECHNICALLY bluchers have one small distinction: the vamp is all one piece, with the eyelet tabs sewn directly on top. The distinction is so minor that we don’t think it’s necessary to differentiate. Call ‘em what you want. 

Derby closure

Derby closure

Blucher closure shoe

Blucher closure

Derby shoes are said to be more comfortable than oxfords, especially for men with wide feet or high arches. A properly fitted oxford is perfectly comfortable for most, but if you plan to be on your feet a lot, derbies will give you a little more breathing room. 

The History of Derbies

The history of the name “derby” isn’t entirely known, but one story is that the name hails from a 14th century Earl of Derby who was, uh, not in top physical shape and had troubles putting on his own boots. A shoemaker allegedly designed the lower, open-laced shoes to make them easier to put on. HOWEVER. We prefer the story of blucher shoes better. 

The name “blucher” comes from a Prussian army officer named Gebhard Leberecht von Blücher who commissioned a re-design of his military boots the early 1800s, during the Napoleonic War.

This new shoe style was more comfortable, allowed for more movement, and was easier to pull on and off, making them better prepared for battle. Von Blücher was a key component to the defeat of Napoleon Bonaparte at Waterloo, so you could call these the ultimate ass-kicking shoes. We do. 

James Bond in spectre wearing derby shoes

James Bond proves that it is still possible to kick some ass in derby shoes.

Today they have firmly established themselves in both business and formal attire, but they’re still seen on modern-day ass-kickers like James Bond. 

Tips for wearing Derbies

As with all shoes, the darker and simpler your derby shoes are, the more formal they are. That being said, even dressy derbies can be worn casually with jeans or chinos.

You should straight lace them for a more formal look, but you can lace these in a crisscross pattern if that’s your jam. Similar to oxfords, details like a rubber sole, broguing, or lighter coloured leather will push it more toward the casual side by default. 

3. Penny Loafer - The Versatile Choice

Sometimes referred to as: Weejuns

Penny loafers

Characteristics of Penny Loafers

Penny loafers are slip-on dress shoes characterized by the leather strap that runs horizontally across the vamp with a slot, which you could fit a penny in if that’s something you’re into. They have a low but defined heel, and the toe often is done in a moccasin construction. 

The History of Penny Loafers

Once again, the origin of the loafer isn’t completely known, but the slip-on style of shoe has been around basically since footwear was first invented. The American penny loafer seems to have a Scandinavian history.

Apparently, American Ivy League students traveled to Scandinavia in the early 20th century and saw Norwegian fishermen wearing a simple, comfortable loafer and brought the style back to The States. This is where they got the “weejun” name. Weejun, Norwegian. Close enough. 

The original penny loafers. Source.

The loafer gained popularity, and in 1936 shoemaker G.H. Bass added the decorative strap with a diamond-shaped slit in the middle that just happened to be able to fit a penny. Not only could you add a shiny touch to your shoes by embellishing them with a penny, but you would also always have enough money on you to make a phone call. Win-win. 

In the 1950s, penny loafers moved from prep-school classics to a dressier shoe style, often seen worn with suits. In 1966, Gucci replaced the leather strap with a metal strap and the look took off.

Matt Damon in talented mr ripley on scooter wearing loafers

Matt Damon's character in The Talented Mr. Ripley sporting metal-strap loafers.

One of our favourite movies for style inspiration is The Talented Mr. Ripley, which features penny loafers a few different ways. White for a boat look, black or brown with a suit and tie. We suggest giving the film a watch if you’re into the “casual elegance” look. 

Tips for wearing penny loafers

Penny loafers can easily cross the dressy/casual threshold. Like our friends in The Talented Mr. Rippley, keep the lighter colours for beachside but feel free to wear brown loafers with a suit, jeans, or anything in between. Black loafers can even be worn with a tuxedo. 

4. Boat Shoes - Don’t slip!

Sometimes referred to as: deck shoesboat shoes

Characteristics of boat shoes

Boat shoes are like the dressed down cousin of penny loafers. They are a moc-toe shoe, but they are characterized by a low, rubber sole without a heel, eyelets on the sides of the shoe, and leather laces.

Boat shoes are often confused with drivers, which have rubber nubs on the sole that are used for grip when driving. Boat shoes are the more versatile and contemporary choice.

The history of the boat shoe

Boat shoes have a clearer history than the previous styles we’ve talked about. In 1934, Paul Sperry slipped off the deck of his sailboat. In 1935, he invented the boat shoe. Sperry got the idea from watching his dog run across icy surfaces without slipping, so he cut siping into the soles of his shoes and the rest is history. 

Sperry’s boat shoes became the official footwear used by the US Naval Academy in the 1940s, but after the war they began to establish themselves in civilian style as well.

Errol Flynn

Errol Flynn, one of the original swashbuckling actors, on the USS Zaca 

JFK and Paul Newman began sporting them in the 1960s, and in the 1980s they were firmly planted in prep style thanks to their appearance in The Official Preppy Handbook by Lisa Birnbach. They have had some surges, but they’ve essentially been acceptable to wear ever since, including their recent appearance in Prada’s 2019 runway

Tips for wearing boat shoes

Lean into the preppy vibes and keep it classy-casual. Wear them with chinos or cotton shorts and short-sleeved sport shirts and polos. Perhaps throw a lightweight cardigan over your shoulders if you really want to embrace the Ivy League look. 

Wear them without socks (or with no-show socks), and expose the ankle by either opting for cropped or cuffed pants. Keep the leather neutral, in browns and tans. 

5. White leather low tops - The New All Star 

Sometimes referred to as: tennis sneakers

Characteristics of white leather low tops

We’re talking about flat-soled, low-top leather sneakers with limited embellishments here. Minimalist and clean, they are a truly timeless shoe. Some people might say they’re the GOAT sneaker. We would be those people. 

The history of white leather low tops

The white leather sneaker goes back to 1965, when Adidas designed the Robert Haillet tennis shoe. Inspired by the canvas shoes seen in basketball and badminton, Adidas produced this version out of leather for a sturdier, more performance-oriented sneaker, and it worked. 

The original Robert Haillet sneakers

At this time, tennis was experiencing a huge surge in popularity, and the shoe style became ubiquitous both on and off the court. In 1971, Stan Smith became the poster boy for the leather low top and the shoes gained--and kept--incredible momentum. 

The ‘80s saw a major resurgence in the leather low tops, seeing spikes thanks to Nike’s Air Force 1 Lows and the Adidas x Run DMC Superstars collab. Gucci also got on board with their leather tennis sneaker in ‘84, which is the first time that luxury sneakers hit the market

Leonardo Dicaprio as Jordan Belfort in Nike low tops

A pair of Nike Cortez low tops can be seen clinging onto Leonardo Dicaprio’s feet in his iconic quaalude-fuelled scene in The Wolf of Wallstreet. (Note: this is not an endorsement of the Jordan Belfort lifestyle).

In 2004, Common Projects broke onto the scene with their Achilles Low sneaker, which re-invigorated the classic style. A perfectly clean silhouette with nearly all branding removed, the Achilles Low became the new standard of sneakers which is still often referred to as the perfect sneaker.

Tips for wearing white leather low tops

The beautiful thing about white leather low tops is that they transcend style rules. Wear them with jeans. Wear them with a suit. Keep them clean and they will always look good. In fact, if you had no choice but to own only one shoe from this list, the white leather sneaker would be it. 

6. Fashion sneakers - The Chameleon

Brunello Cucinelli knit sneakers

Characteristics of fashion sneakers

Here we are talking about sportier-looking shoes than the clean, white leather low tops above. Not necessarily defined by any one style, these are the ever-morphing, trendsetting shoes that sneakerheads clamour over and the average person finds themselves wearing almost by accident (probably after poking fun of them when they first emerge).

Perhaps you’re on the ball with emerging styles and have the latest New Balance Hierro shoes, or maybe you prefer a more refined approach like the Brunello Cucinelli knit sneakers. Either way, fashion sneakers are so ingrained in our culture that they tend to become a part of our life without us even realizing it. 

New Balance Hierro v5s

The look of fashion sneakers are always going to shift, and while you don’t always have to own the latest and greatest, this is one shoe that we recommend refreshing every couple years. 

The history of fashion sneakers

The history of the sneaker is a  never-ending rabbit hole that dates back to the 1700s. We aren’t going back that far.

Keds and Converse can be thanked for the original sneaker in the early 1900s, and as you can probably guess, Adidas played a major role as well. But it wasn’t until the 1950s that sneakers started to become seen as a fashion shoe, which can be attributed to the cool-casual looks of James Dean and Marlon Brando.

James Dean makes everything look cool, including sneakers. 

Sneaker culture is a monumental part of fashion history, and if we tried to list all the iconic sneakers throughout the years this article would never end. Some major moments we love have been the rise of the dad shoe via the New Balance 990 series, the futuristic Reebok Pumps from 1989, Kanye West’s decade-defining Yeezy Boost 350 launch in 2015, and literally every iteration of the Nike Air Jordans. 

Marty McFly knows what's up. 

Our favourite iconic sneaker moment? The self-lacing Nikes from Back to the Future. 

Tips for wearing fashion sneakers 

Fashion sneakers should usually be reserved for your weekend looks, but this style of shoe is always breaking and making rules, so take a risk. 

Maybe you’re taking inspiration from Spike Lee’s sneaker-featuring red carpet looks, or maybe you like to keep your casual shoes casual with jeans or joggers. With enough confidence, you can wear them just about any way you want. 

Questions about footwear? Get in touch. 

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