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Explaining the finer points of men’s shoes is a sticky situation. The nuances often come down to the smallest detail on a strangest part of the shoe. We’re here to help you understand these variances and #UPYOURSHOEGAME

Take for example – the difference between a Derby and an Oxford – where the eyelet tab is stitched into the shoes, instead of the tabs sitting on top of the shoe. GenericPuzzles is here to help you unravel the brain bending world of shoes.

Traditionally there are 6 varieties of shoes – we’re here to explain them all.  Time to get you style game on form.



The characteristics of a loafer – a completely laceless shoe, low cut with ankle exposed, separate sole, low heel and usually upper vamp (where the laces would be).  Classically the loafer has a moccasin, which is frequently of a contrasting fabric or color across the vamp.

Loafer shoes are unique as they have developed on different continents. Loafers in their earliest incarnation are believe to have developed from Native American moccasin style by a Norwegian designer.

The contemporary loafer style we know today, dates back to the 20th century, where they were made to be a casual take on the Oxford shoes – consisting of a basic Oxford design, without the laces – et voila the Wildsmith loafer was born.

Many people confuse a slip-on with a loafer – however they are not the same. Slip-on shoes do not require a moccasin seam on the upper (which a loafer most certainly does)– and can look like an oxford or brogue.

Due to its heritage, a loafer will never be a formal shoe, it’s regarded as an inappropriate shoe to wear with a classic 3 piece as it’s simply too casual. For an informal and moderately formal situations loafers are appropriate, and are ideally worn for garden parties, with light and summer suits they can be complementary. You can sometimes wear a summer suit or casual suit with classic style darker loafers or with tassels.


Many men in the US call all laced dress shoes an Oxford, it has become a branded term – like Kleenex or Wrigley’s – technically however this is incorrect. An Oxford is characterized, by the eyelets being stitched into the shoe, as opposed to sitting on the shoe. It also possesses a tightly intertwined lacing system, low heel and exposed ankle. There is a pretty clear distinction between the Oxford and a Loafer, as opposed to a Derby or Brogue – which is more nuanced.  Essentially the Oxford’s design is meant to give the impression of a sleeker, classier shoe tailored to formal situations.

Oxford’s first originated from Scotland and Ireland, where they were called Balmoral’s. Stylistically they were plain, formal shoes, made almost exclusively from leather. In modern times designers got more exotic and creative with their design work and Oxfords are now made from calf leather, patent leather, suede and canvas.

It may seem bizarre, but the idea of wearing Oxford’s initially was rebellious – they were the Doc Martens of their day. Yes on the mean streets of Oxford University a rebellious shoe was designed.

During the 17th century male footwear was dominated by boots – often going up to knee length – which seems outrageous today. They were also super-tight fitting with buttons instead of laces (what a drag). More often than not these boots featured rather high heels, a style that was popularized by King Louis XIV due to his small statue. At that time France was defined as the epicenter of the fashion world and as such most European gentleman aligned themselves with the choices of the French establishment.

Slowly England became the trend setting hub of the universe, much to the disdain for the French.

It seems that the Oxford shoe is actually a descendant of the “half boot” Oxonian – from around 1825. The Oxonian slowly shortened to the  ankle as people got more and more ‘rebellious’– and the laces, which were on the side, initially moved up to the instep – there is some debate about if all these changes  took place on campus, of course it seems highly improbable, but it makes a neat story.

During the 1800’s men wore the oxford for formal and social gatherings – the toes could be rounded, square and decorated with stamped leather – which we called wing tips or cap-toes.

They were exceptionally popular as early as the mid-1800s with the upper crust at Oxford University. They were notably popular with rebellious young people who wanted a change from ankle boots and knee-high boots that were popular at the time. Some claim that the oxford shoe emerged from Scotland and Ireland and are referred too as the Balmorals, after Balmoral castle. However what is clear is that gentleman were looking for a comfortable, fashionable shoes that could be worn for walking.

Joseph Sparkes Hall, the inventor of the Chelsea boot, when referring to the Oxonian noted that it is the best shoe for walking. From there it was a short step to being acceptable as the premier choice of men’s footwear, replacing boots that were now relegated to specialized activities such as horse riding. Ironically the Oxford shoe – although it has a history assigned to the campus, is probably too formal to be considered and everyday shoes for campus wear today.

Oxford’s form the base for derby’s, wingtips and brogues and come can in cap toe on wing tip tops. They are very flexible shoes – suitable for casual and formal events. It should be noted that Oxfords are not always Brogues and brogues are not always Oxfords.


Chelsea Boots: you know the one – close-fitting, ankle-high boots with an elastic side panel. They often have a loop or tab of fabric on the back of the boot enabling the boot to be pulled on.

Chelsea boots are considered an iconic element of 1960’s Britain, particularly in the mod scene and rock scene, they resemble renegades of a generation. The boot actually has deeply regal roots Joseph Hall who designed them for Queen Victoria.

The Chelsea boot we know today however, owes much to the invention of vulcanized rubber by Charles Goodyear’s. With the advantage being the development of elastic – the corner stone of a Chelsea boot. Joseph Sparkes Hall on filing his patent in 1981 claimed that Queen Victoria walks in these boots daily – giving his boots the social proof of the highest kind. They were initially called “elastic side ankle boots” which is a bit more wordy than the current branding – we’ll get more on that later.

According to Chelsea boot’s inventor they were popularized as walking boots, tailored to both men and women. Indeed ankle boots were the dominant style of shoe worn at day time.

The style remained a staple up until WW1 – where it fell out of fashion. By the 1950’s Chelsea boots renaissance was now under the wing of a plethora young artists, film directors and socialites that started to frequent the King’s Road area in London – the group was dubbed the “Chelsea Set” by the media. This group was well known and fashion forward including icons such a Mary Quant and Jean Simpson.

Angello and Davide re-interpreted the Chelsea boots in the 1960’s fitting with the Cuban heel. This was known as the Baba Boot – which was popularized by the world of rock and roll, where it was plugged enthusiastically by the Beatles, where predictably the popularity skyrocketed. This was then followed by the image conscious mods, who considered them the height of mod fashion, wearing tailored suits on customized scooters.

It is not hard to ascertain why the Chelsea boot was so popular- wearers included a who’s-who of fashion icons. Not only did well known rock bands, such as the rolling stones wear them but also French & Italian cultural influences fused for the popular American greaser look.

As a style, Chelsea boots are popular due to their versatility and classic look. They can be dressed up, down and then back again very easily. Chelsea boots are a timeless look with a nod to the past. Their simple clean lines compliment virtually any outfit – they have been featured by designer across the spectrum from high-end couture to low-end budget fashion.

Chelsea boots have 7 standard characteristics:

1. Ankle Length
2. Rounded Toes.
3. Low Heels
4. They are made from two pieces of leather and meet near the ankle.
5. The vamp and the quarters meet near the ankle where they are joined by a strip of vulcanized rubber or elastic.
6. The strip of elastic extends to just below the ankle but not all the way down to the sole (just above the welt).
7. The vamp and quarters are not sewn one on top of the other. Instead, they are sewn together in one plain below the ankle.


Modern Brogues’ trace their origins back to a rudimentary shoe, originating from Ireland and Scotland where they were made from untanned hide. Far from exotic, the initial perforation (those dainty dots) were designed as a drainage system allowing water to drain from the shoes when the wearer walked across bogged terrain – lovely.

There was nothing romantic about the brogue back then, the name is derived from the Gaelic “brog” which means ‘ a rough or stout shoe’ – the world Merriam-Webster dictionary describes ‘broguing’ as an ornamentation of shoes employing heavy perforations and pinking. A true union of fashion and function!

Of course at that time the brogue was not considered an appropriate style of shoes for casual or formal situations. How time flies – the ugly duckling turned into the beautiful swan, from Irish farmers to the red carpet. Nonchalant!

Although Brogues are similar to the “Oxford shoe”, they are two completely different types of shoe and are not to be classified into the same family, just so you don’t get it twisted.

Brogues are most commonly found in one of four toe-cap styles (full or “wingtip” brogues, semi-brogues, quarter brogues and long-wing brogues).

The brogue is a super versatile shoes and can be worn in a variety of occasions – it is also ultra in trend and has remained a classic style for decades.


Before the advent of the modern boat shoe, sailors and boatmen alike struggled to maintain a firm foothold on the slippery decks of their wave engulfed boats. The shoes available to them were simply not up to the arduous task of assisting sailors to keep balance on deck, of course this led to frequent accidents, not to a mention a regular stream of hilarious and embarrassing situations.

In the early 1930’s, Paul Sperry, an ardent sailor and boater was struggling with this problem in his everyday life. Luckily, he came across as very unlikely muse in his dog. Here’s how the story begins:

One winter day in Connecticut he took his dog, a Cocker Spaniel by the name of Price, where he was amazed at his dogs ability to grip the ice while running.

The traction he managed to generate on slippery surface intrigued him – how did he manage it? Paul figured that it had something to do with the pads on Price’s feet.  Upon closer examination of his dog’s paws he realized that Price’s feet had formed herringbone-like pattern that allowed him to grip wet surfaces remarkably easily. With this brain wave he started upon his million dollar idea.

In 1935 the Sperry Top-Sider shoe with mid to calf-brown leather upper and white rubber sole, with herring bone mold were introduced to the market and quickly gained prominence among sailors. By 1939 the navy had recognized the benefits of the boat shoes and started to manufacture it for its sailors. 

The style and manufacturer has become some what of a heritage brand and they are still worn today, on the boat and off the boat.

For obvious reasons the boat shoes should be avoided during winter, unless you live in a hot tropical climate. They are best paired with slim, clean lined jeans or shorts.

Dark denims provide the best combination for boat shoes, especially when accompanied by with a polo shirt or oxford button down. Boat shoes are informal, casual footwear – so don’t go wearing them with a suit, sports jackets or blazers. Similarly, you should never wear these to dinner parties – these should be reserved for days relaxing in the park.


Chukka Boots are ankle-length leather boots with suede or leather uppers. Chukkas are usually made from calfskin or suede, although thy have been made by more unusual materials like crocodile skin. The style first became popular in the late 1940’s through the 1960’s as casual wear and were worn by British forces in the Western Desert Campaign of World War II.

Nathan Clark, was an officer in the royal army service corps, posted to Burma in 1941 with orders to help establish a supply route from Rangoon to the Chinese forces at Chongqing whilst also launching series of offensives throughout South East Asia. Although he did all this work you probably won’t recognize him from his military days, but instead from his shoes – Clark’s – in shopping malls around the world.

The desert boot has success in Italy and France and which was later released in England and US. In the US the desert boots became popular with the beatnik culture and was later adopted by the 1960’s mods. The mod look is still strong today; Paul Weller and Liam Gallagher sport desert boots regularly. In its 60 year history Clark’s deserts boot has sold more than 12 million worldwide.

Chukka boots are always casual, and should never combined with dress pants or suits. Suede Chukka boots with crepe soles should only be worn with denim or chinos.


Monk strap shoes are becoming increasingly popular with the style set, year-on-year and its heritage comes from exactly as you might imagine. The monk strap shoe found popularity with monks in Europe because it was more protective than the sandals that were traditionally worn. They were hard wearing and long lasting, making them a solid choice as a work shoe and durable for heavy walking.

The obvious hallmark of a monk strap shoe is the lack of lacing – the shoe itself is very similar to a standard brogue shoe, traditionally, monk shoes are ranked as a middle of the road for shoes – they are considered too informal for suits. However, it is the detail that sets – the incarnations of the monk shoe are endless, single strap or double – made from suede or leather and can be worn with socks or without.

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GENERIC SCIENCE: #BeardMaintenance


There was a time when growing a proper beard required only one thing – the face’s owner to simply cease shaving.

These were simpler times, your choice between a beard or an arsenal of shaving tools: shards of flint, volcanic glass, scallop shells and a host of, what seems like, pocket sized medieval torture devices.

Today you have options.

Nobody wants you wandering round like you have a Weetabix strapped to your face – ambling through life like a time travelling Viking – so we have some beard 101 advice:

  • 1. If you’re just a young pup or abnormally hairless, shave twice-a-day for some time before dedicating yourself to beardom – no beard is better than half-assed one.
  • 2. Accessorize, it’s time for a top hat and cane, possibly pocket watch… at least a new scarf. You haven’t just grown a beard you’ve grown a new man, go get ‘em Heisenberg.
  • 3. If you’re overly hairy and intent on a developing a resplendent manometer, shave above your cheek line – no stragglers. As a rule, neatness is classy – stay classy.
  • 4. Invest in a reputable barber of some esteem, and a trimmer of equal quality – you’re in the major leagues now, son. No cheap fixes.
  • 5.  Invest in fine tooth comb, but no using it in public – you filthy animal.
  • 6. You must never tend to your beard; you must only nurture. He’s part of you now. With nourishment and boundaries in equal measure you two will be partners in crime.
  • 7. Trim to a shape that enhances your features – don’t go for the beard’s version of the comb-over. Follow there simple rules: if you’re brown give it the volume it needs; if you’re light cut it shorter.
  • 8. Treat your beard as if it were your scalp – that means soap and conditioner. Only these two in careful quantities can itch free relief be attained.
  • 9. If itchiness is proving to be a complication in your relationship, follow the Rugged Fellow’s Guide and choose a high neckline, close to the jaw and shave beneath it. Science.
Trimming A Beard Neckline

10. A ‘no-no’ roll call: Neck Beards, Goatees, The Horseshoe (sorry Mr. Hogan), the mutton chops OR the Chin Tuft & Mustache combo aka the ‘Colonel Sanders’.