Ankle boots, pumps, ballerinas, sandals, plateau and high heels are all different shoe types. You first have to find your way through all those terms which you might have already heard somewhere. And although most of these words are related to women’s shoes, there are also lots of different men’s shoe types. This can be confusing in the beginning especially if you are not familiar with them (yet).  A well-dressed gentleman should definitely know what distinguishes a Derby from an Oxford shoe. It’s also good to know what the features of Loafers are and that the term “Monks” does not necessarily refer to religious persons. But let’s address everything step by step. After all, men mostly do not intend to buy 5 pairs of each type. Instead they want to find the “right” shoe.

Monks – dress shoe alternative to Oxford and Derby shoes

It is believed that the commonly known Monk Strap Shoes have been invented by a monk. Initially he created them as a sandal. However, as you cannot wear a sandal all year long, they received a closure. Over the years they developed into the Monk Strap we can find on the shelves in shoe shops today. This type of shoe became very popular in recent years and it is definitely a must-have for every man’s wardrobe. You can see a lot of men wearing Monks at Pitti Uomo. Often without even closing the buckles – this gives it a certain nonchalant look. 😊

Single and Double Monks

The Monk is actually based on the classical Derby. This shoe has a very classic style with additional pieces of leather attached to the vamp of it. The only difference is the design of the strap closure. Derby shoes are usually closed with laces and have no strap. In general, the strap(s) are even more convenient for men, as they can be easily opened and closed. Perfect for men who are rather impatient or have a stressful day and no time for tying shoes. If the shoe has two straps, then it is called “Double Monk Strap” or simply Double Monk. Monks with only one strap are Single Monks. There is no practical advantage for having two straps instead of only one strap. So the buying decision will be mainly based on aesthetics. However, impatient men might prefer closing only one buckle per foot instead of four in total. 😊

Double Monk Straps

Due to their straps, you can barely find any perforations on Monks. Otherwise the shoes would look overloaded. Most often they will be plain or have a cap toe. However, you might find Monks with some perforations, especially in the wing tip area. Those might be fine for rather casual but not for formal and business meetings. Nevertheless, you can pair Monks perfectly to a classical or to a linen suit. But they can also be wonderfully combined with jeans. Similar to all other shoe types, you will find a wide color range for Monks. The more formal the occasion, the more you should refrain from Monks with flamboyant patinas.

Loafer – not only a shoe for the summer

A loafer should not be confused with a moccasin, as the latter ones have no heels. Moccasins are made of very soft leather and very often used as shoes for driving a car. Loafers have neither laces nor straps, so they are rather a slip-on shoe. To date, the loafer is a shoe for more casual days. But – depending on the entire outfit – it can also be worn to the office. The comfortable slipper e.g. can be worn to a garden party in the summer (with socks which are not visible when wearing the loafer, please!). However, important and formal office meetings are more likely to be attended wearing an Oxford or a Derby.

The Penny Loafer

One of the best-known Loafers is the Penny Loafer, also known colloquially as the college shoe. This shoe version was developed and manufactured in America, initially by the company Bass. In the 1930s they have introduced the shoe to the universities. The Penny Loafer has a decorative leather strap which runs horizontally across its vamp and has a cut. Back in those college days, a telephone call would cost the students one penny. The small opening in the loafers was perfect to fit exactly this coin. This is where its name comes from.

The Tassel Loafer

If you like the style of Loafers and want to wear them in the office, try a Tassel Loafer. In America, this type of shoe is already recognized as a business shoe. However, in Germany it is not very common to wear it in the office. Here, you mostly use Loafers in combination with jeans or chinos. Men in Germany aren’t fully convinced by Tassel Loafers due to those typical tassels. Usually they are considered as disturbing and possibly not very manly.

Most often you would associate Tassel Loafers with men from Southern countries. But more and more shoemakers are incorporating this shoe type into their production. They create more discreet tassels and use wonderful high-quality leather. In general, Loafers, regardless if Penny or Tassel Loafers, can be perfectly worn in spring and autumn, too. In colder months, you would pair them with nice socks which will fully complement your attire. Please make sure that your socks are long enough to go over the calf. There is nothing more disturbing than socks which reveal part of your leg flesh. This however is a general rule relevant for any type of shoe worn by gentlemen.

Chelsea Boots – the classic shoe for colder months

Chelsea boots are shoes for lovers of classical footwear, even if they cannot always be properly paired with a suit. Many know the Chelsea boot as “Beatle boot”; a shoe which has been originally designed by Queen Victoria. This type of shoe is similar to ankle boots. Back at that time they were commonly used for horse riding due to their comfort. Later, the shoe became more and more popular and it is especially wonderful for colder months. If you’re living in a region, where it gets really cold in the winter, you can opt for Chelsea boots which are fur-lined with a thicker (preferably rubber) sole. This will keep your feet warm and you will be still looking like a well-dressed gent.

Chelsea Boots

Its unique feature is that it reaches above the ankle with stretchy rubber band inserts  on both sides of the upper. These are intended to make it easier to put on the Chelsea boot and to provide support for the foot. Thus today, this shoe definitely shouldn’t be missing in a modern wardrobe. It’s mostly the ladies who appreciate this type of shoe more than men.

In fact, it is difficult to combine the Chelsea boot with a formal outfit – in most cases its edges will become apparent under the pants. Nevertheless, the Chelsea boot is quite suitable for various occasions; you just have to know exactly how to pair it. It goes well with jeans. If you want to give it a cool and nonchalant look, roll-up your jeans a little bit. Perfect!

Classical shoe types are timeless

Perhaps now one or the other gentleman can understand, why women “need” so many shoes. After all, not all men’s shoes can be well combined with every outfit. Depending on the occasion and the attire, you have to decide if the shoe should be more elegant and simple rather than extravagant or flamboyant. But don’t be afraid of choosing the ”correct“ shoe for your next business meeting. Most classical shoes are absolutely timeless, so you will always look fashionable and stylish. In fact, most shoe models have been developed as early as the 19th century. To this day, classical men’s shoes such as the Oxford, Derby, Loafer, Monks and Boots have proved to be THE shoes. They should be part of every well-dressed gentleman’s wardrobe.

Yes, shoes are more than just a fashion statement; they express your own style. And that’s why it is fairly important to know the latter and to combine the appropriate shoe with it. You should always feel comfortable with what you’re wearing – disguising is nearly as out as open laces are.