Men’s shoes. How can something as simple as what we put on our feet become so complex?
A guide to men’s shoes is something the Gentleman’s Guide has always lacked. Not because we didn’t want to write about it, but rather because the subject is so complex. Internet style forums are full of threads where each shoemaker’s craft is weighed against others in a jungle of terminology, brands, shoe models and good and bad advice.
In this guide, we guide a modern gentleman through the complex world of men’s shoes with the aim of giving you a good general knowledge of the subject – key shoe models, great brands, wise buying advice, some style tips and a touch of history.
For those interested in the details, we will be releasing a large number of deep dives on the subject of stylish men’s shoes in the coming weeks and months. So kick off your shoes, slide down the couch and dig in.
Table of contents
- Five models of men’s shoes you always need
- Low shoes
- Summer shoes
- Buying advice: How to find stylish men’s shoes
- Forestry wardrobe – how many shoes do I need?
- The construction of the shoe
- Sizes and loads
- Shoe manufacturers – an overview
- Tailor-made shoes
- Premium brands
- Quality labels
- Everything else
- Dressed up
- In everyday life
- On the beach
- The history of men’s clothing
- The age of sandals and moccasins
- Long, wide and high shoes in the Middle Ages
- High-heeled shoes, knee boots and tights
- 19th century: The birth of the modern men’s shoe
- 20th century: Shoe fashion reborn
- 2000s: The era of the sneaker
Five models of men’s shoes you always need
If you have ever visited a right shoe store, such as a Crockett & Jones store in London, you will know how many shoe models there are. When do you use them and how many shoes do you really need? Here are five categories of shoes that you should have at least one of each in your shoe wardrobe.
Dress shoes are the formal shoes worn with a suit. These are probably the first pair of real men’s shoes you will buy in your life, and if you buy the right ones, you can wear them for many decades.
Low shoes can be divided according to their construction into oxford och derby ( or balmorals respectively. bluchers as the Americans say ). The difference is in how the lacing is constructed. An oxford has a closed lacing where the holes are directly into the leather on the top of the shoe, while a derby is laced via two ‘wings’ that sit on top and above, known as ‘wings’. open lacing .
A lot of people around you won’t notice or care, but an oxford looks more traditional and formal than a derby and therefore goes well with a dark suit. A derby, on the other hand, looks more modern and thrives with a much wider range of clothing, such as jeans and chinos.
A more unusual version of the low shoe is the monk shoe, which fastens with a buckle. This style can look great, but it’s overkill and best suited to those looking to add some variety to a larger shoe wardrobe.
Brogue is not a shoe model – a common misconception – but a decorative stitching made of perforated leather, which can be found on derbies, oxfords and boots. The decoration makes the shoe less formal and is often associated with Britishness. country life. In our everyday Swedish life, it is a well-dressed choice for jeans, for example.
Loafers are also low shoes, but without laces. The concept has been around for a long time, but became really big in the 20th century when it was adopted by students at American Ivy League universities and wealthy tourists vacationing around the Mediterranean. The difference with a moccasin is that a loafer usually has a sole, making it a more dressy shoe.
The two basic models are penny loafers , decorated with a band across the foot, and tassel loafers which has tassels. For the undecided, choose a penny loafer first, which is more discreet and easy to match. Originally, loafers were made in leather, but brown suede is also very stylish.
You can think of loafers as a stylish replacement for sneakers (yes, we know – it should be the other way around, but today many people grew up with sneakers first!), but also as the perfect summertime shoe for a suit. There’s a reason Italians love loafers.
In the Swedish climate, you won’t be able to wear low boots all year round. But boots don’t have to mean military boots – there are stylish boots that can easily be worn with a suit.
The basic types of boots are chukka boots , basically high versions of classic low shoes, chelsea boots , which has an elastic side, and lace-up boots. Desert boots is a specific type of chukka with a crepe rubber sole that is best suited for warmer seasons.
When choosing boots, keep in mind that this does not immediately mean that they can withstand water and snow. A shoe with a leather sole will take a beating in rain and sleet, no matter how tough it looks. It will also be very slippery. So for winter, boots with a rubber sole – the more elegant studded sole (often referred to as Dainite sole after the trade mark) or the larger commando sun – often the best.
A good starting point is a chukka or Chelsea boot in dark brown leather or suede, which will work with most types of fall and winter clothing.
“Can sneakers be placed on a list of classic men’s shoes?” I hear the shoe connoisseur shout. Yes, they can. Once upon a time, sneakers were cheaply constructed trainers. Today, some sneakers are made with almost the same level of ambition as a pair of classic men’s shoes.
Minimalist white sneakers or leather/suede sneakers work well with many styles of clothing except the most formal, such as a suit. Just make sure you choose good quality, stylish sneakers and take good care of them.
Many shoes are best, or only good, in summer. In this unrelated category we include moccasins, sandals (leather or suede, not plastic!), espadrilles, car shoes and sailing shoes.
These are shoes you will need, not least to avoid ruining your other shoes, or looking like you ran away from the office on a sunny summer day. These shoes are best worn on the beach or along the promenade. Don’t bring them to the office, and don’t wear them with a suit, and you’ll be fine.
Buying advice: How to find stylish men’s shoes
Forestry wardrobe – how many shoes do I need?
Think of your shoes as a wardrobe rather than individual shoes. You will need a set of shoes for different needs, and preferably a couple of alternatives for the same situation so you don’t wear the same shoes two days in a row.
A good starting point is around 10 pairs of men’s shoes. Start by choosing one of each from the categories above, such as
- a black oxford for formal occasions
- a pair of dark brown suede loafers for the warmer half of the year
- a pair of brown Chelsea boots for winter
- a pair of stylish white sneakers (not counting everyday shoes or trainers).
- a pair of espadrilles for the holidays
Then add something complementary and mix and match based on lifestyle, e.g. a brown derby shoe, some loafers, sneakers and sailing shoes or car shoes for warmer days, a pair of more dressy boots and a pair of leather sandals for the beach. Of course, a lot of it is about your life and your needs – if you wear a suit every day, you’ll need (be lucky enough to own) a lot more flats.
The construction of the shoe
There are three basic ways to put together a sole and the shoe’s upper or top: gluing, sewing, or using a edge (world) .
Glue is the cheapest and the worst from a durability perspective – you won’t be able to resole the shoes if the sole wears out, and the glue will sooner or later (often sooner) come off. If a manufacturer glues the shoes, it is often a sign that they have skimped on the rest of the shoe as well.
Sewing on the sole is called by a fancier word Blake design or that the shoe is quilted. The outsole is simply sewn on from underneath with stitches (lock stitch) from a special machine. This is simple, requires no special construction and produces a soft and flexible shoe. The disadvantage is that the stitches puncture the outsole and the holes allow water to seep in. Although the sole can be replaced, the perforation also gradually destroys the interior of the shoe, and eventually it will not be possible to re-sole the shoe again. Blake-designed shoes are an acceptable but not perfect option, as long as you don’t pay too much for them.
The best way to fasten a sole is to use a so-called stripe or world in English. The welt is sewn to the upper and then the outsole is sewn to the welt. The result is a waterproof and durable construction that can be re-soled many times. With proper care, a men’s welted shoe can last many decades. The only downside is that the shoe will be a little firmer, requiring breaking in, and a little bulkier (not that you’ll notice) than a shoe with a Blake construction. On the other hand, the construction requires the space between the sole and the shoe to be filled with cork, which creates a structure that molds to the foot, making the shoes more comfortable over time than other shoes. On the finest shoes, the striping is done by hand, hand welted , and otherwise it is called Goodyear welted after the inventor of the machine. There are also other edge-cut variants such as Norwegian welt / storm world och Field Shoe which provides even more watertight structures.
A good starting point is to opt for a welted construction on all your classic low shoes and boots. Just keep in mind that the stripe around the sides of the shoe does not necessarily indicate that a shoe is welted. Many manufacturers cheat by adding decorative stitching or plastic seams that serve no purpose. You need to either inspect more carefully or simply ask if the shoe is welted. When it comes to other types of shoes like sneakers and summer models, construction is more about craftsmanship than technique – here the manufacturer is the guarantor of quality.
Good shoes are made of leather or suede. The material should preferably be so-called full grain , which means that the entire leather was used and not just one layer of it, known as a “single layer”. top grain . There are of course more dimensions of leather quality as well, which is of course difficult for a layman to judge. Choose a reliable brand and you can expect good leather. By waxing or oiling the leather you get qualities that are more water resistant.
Patent leather is a treatment (basically a wrapping) of the leather, invented to keep shoes shiny without shoe polish. Today they are mainly used for formal shoes, such as a pair of patent leather oxfords for a tuxedo.
Cordovan is another unusual material, made from horse hides, which often costs more but produces very durable shoes.
As for the soles, the starting point is a leather sole. Soles made of cheap rubber, plastic materials etc. are normally a bad sign for low shoes. However, a leather sole is delicate, best suited to offices and big cities, and many manufacturers offer treaded or non-treaded soles. city soles In Sweden, where we have a penchant for pouring sand and gravel on the streets, this is a good investment. For boots and coarse shoes for autumn and winter, soles made of Dainite or Vibram (durable rubber compounds) and Commando soles with patterns are good for water resistance and better grip.
Sizes and loads
A classic men’s shoe has not only one measure, but three important dimensions. Fit, length and width.
Firstly, different lasts, or models of feet, are used when making men’s shoes. Fine manufacturers often have several lasts that can be quite different in shape, from narrow to wide. So just because you have one size in one last does not mean you will have the same size, or fit at all, in another last from the same shoe brand.
As for the shoe size, it is only an indication of the length of the shoe, not an exact science. As most people know, there are European, British and American shoe sizes.
The European shoe size indicates the length of the leather in 2/3 cm. To get some space between your toes and the leather, you need about 2 sizes (1.3 cm) more space than heel to toe, so the correct way is to take the length of your foot times 1.5 (or divided by 2/3) + 2. For example, if your foot measures 28 cm, you have shoe size 44.
In the United Kingdom and the United States, the reading is measured in 1/3 of an inch. barleycorns but measured from different starting points. Size zero in the UK is 8 1/3 inches. Yes, we are serious. So a shoe built from an 11 inch long last is a size 8 (8 * 1/3 = 2 2/3). With 2 barleycorns of space for the toes, the correct formula is the length of your foot (in inches) times 3 – 23. If your foot measures 11 inches, you have shoe size 10. To get your American shoe size, you add 1, i.e. shoe size 11 in the case above.
However, as not all manufacturers are so strict, you should always check size charts if they are available.
The last thing to consider is width. There are a number of different systems here too, but the most important thing to know is that “higher” letters mean wider shoes. The normal is either D, E or F, so if you feel, for example, that width E is too narrow, see if there is an F (or sometimes EE).
Shoe care is a topic in itself, so we’ll settle for listing our three most basic tips to make sure your stylish men’s shoes stay just that:
- Choose shoes according to the weather The quickest way to ruin shoes is to choose the wrong shoes for the weather. Rain and sleet can quickly ruin a nice pair of men’s shoes, especially salt streaks are very ugly and hard to get rid of. In summer, the biggest problem is foot sweat from wearing shoes that are too hot.
Protect your shoes. In winter, choose sturdy shoes or use galoshes (rubber protectors), waterproof them well and dry them thoroughly if they get wet. In summer, choose thinner shoes such as loafers, use foot deodorant or no show socks such as these that absorb moisture and allow your shoes to dry if you get sweaty in them.
- Give your shoes some love Clean your shoes regularly and they will look good and last better. Great shoes deserve great products – French brand Saphir is a great brand for men’s shoe care products.
Buy a kit with brushes, cleaning cloths, shoe polish and waterproofing spray – it’s worth it! A nice whiskey and some shoe care is actually not that hard. How often you need to take care of your shoes depends on how often you use them, but don’t forget that even shoes that sit in your closet will eventually dry out, so make sure to give all your shoes a once-over per season.
There are also special products for sneakers, such as these sneaker cleaning cloths from Jason Markk.
- Rotate your shoes : Just like people, shoes need a little rest after a hard day’s work. When you have used your shoes for the day, first make sure they are dry. If not, stuff them with paper towels and place them somewhere warm and dry. Then insert a pair of shoe blocks to keep the shoes in shape. Choose a different pair of shoes the next day and let yesterday’s shoes recover. Shoe blocks should be made of wood, such as cedar – not plastic!
Shoe manufacturers – an overview
Where to find good-looking, high-quality men’s shoes? There are, of course, a plethora of shoe manufacturers, and we can’t go through them all individually. Instead, we’ve divided the world of footwear into a number of groupings. Generally speaking, the “higher up” you go in this pyramid, the better shoes you get, but not everyone can afford to spend that much money on a pair of shoes.
Or should it be called cobbled shoes instead? Bespoke shoes means that the shoemaker makes a model – the last – of your foot in wood through individual measurements and then builds the shoe according to your anatomy. The last is saved and becomes the starting point for your future orders.
This is, of course, a great product that allows you to influence the design of the shoe and get a shoe that fits perfectly on your foot. The only problem is that prices often range from 50,000 SEK and upwards with the most well-known names and a few tens of thousands of SEK with shoemakers in cheaper countries.
Do not confuse tailor-made and made-to-measure ( made-to-measure ) shoes. Made to measure means that the shoe is made as close to your measurements as possible, from an existing model, but not from a personalized last. As a result, made-to-measure is often much cheaper than bespoke – sometimes only slightly more expensive than a ready-made shoe from the same manufacturer would cost. This can be an option if you want and can afford nice shoes, but can’t quite get the sizes right.
Among footwear sold in shops, so-called ready to wear (RTW) There is a hierarchy that can be debated for hours on shoe forums. What is clear is that the top shelf starts somewhere north of €5,000 per pair, and rises to €20,000 per pair. We are then talking about shoes from shoe brands – of course, there are also very expensive shoes from fashion brands, but whose quality does not match the price level at all.
For that price tag, you should expect high quality striped leather shoes with a very elegant finish on both the upper and the sole. The shoes should have been produced by the brand’s own craftsmen in its own factory.
The brands often ranked highest and priced accordingly are Edward Green, John Lobb and Gaziano & Girling – all from England. Confusingly, there is another John Lobb headquartered in Paris (johnlobb.com), owned by Hermés, with similar prices but a little more focus on fashion. Other names that might come to mind are the British Church’s, which has run into trouble after raising prices substantially, and the French Corthay and Aubercy with their distinctly French long-toe models.
Slightly below in price (on the right side of 10,000 SEK) but still fantastic quality are names like Crockett & Jones, George Cleverley, Trickers, Alden, Carmina, Enzo Bonafé, Vass, Ed Meier and others. The price difference is about details in the finish and if you had not known that Edward Green existed, you would never be dissatisfied with any of these manufacturers. If we were to pick one brand, it would be Crockett & Jones, because they have high quality, a large range, plenty of retailers and have been very consistent over the years. But a lot of this is a matter of taste.
Not everyone can or wants to pay €5,000 for a pair of men’s shoes. However, it is important to understand that you get what you pay for. Shoes made by hand in the US and Western Europe will cost thousands of dollars. The only way to bring the price down is to either lower the quality of materials and craftsmanship, or find cheaper labor.
In the category of quality brands are the companies that have chosen the latter. They still make high quality shoes but in countries with lower wages, such as Spain and Portugal in Europe. The shoes are often made by shoe factories that work with many different customers. The construction is of course a bit simpler and the finish is not as perfect, but for 2,000 SEK you can still find very good shoes.
There are hundreds of brands in this segment. In the UK, there are many brands with production around Northampton, such as Loake and Barker. In America, there are brands such as Allen Edmonds and Cobbler Union. In Spain, there are Yanko and TLB, to name a few. Most of our quality Swedish brands – Myrqvist, Morjas and Skolyx – as well as Oscar Jacobson’s shoes fit in here, as their welted shoes are made in Spain or Portugal.
When you go below about €2,000 for a pair of classic men’s shoes, you can no longer expect good quality. You will either get a pair of shoes that are not edge-stitched, but at worst glued, or a pair of shoes made by inexperienced workers. The exception is simpler shoes like sandals, espadrilles and sneakers (especially in canvas) which are obviously much cheaper to make.
As a result, you will want or need to buy a new pair of shoes again soon. In addition, your new shoes will age quickly so they won’t look very good even when they are still new. Instead, use sales to find good deals, or simply buy fewer but better shoes.
Giving style tips for an entire category of clothing is of course hopeless. However, we want to point out some basics on how to combine shoe models with clothes.
A high quality pair of oxford shoes is the easiest match for a suit and tie. Examples of uses include christenings, weddings or fancy parties. For those working in a bank, law firm or consultancy, it is an office shoe.
Black gives you the most flexibility – black shoes go well with gray, brown and dark blue shades of the suit, and can also be worn with a blazer and dark jeans.
For winter, you can swap your oxfords for a pair of boots, but be careful not to choose a shoe that is too coarse. A Chelsea boot is an excellent choice, as its lack of lacing gives a very clean look on the foot.
Wear your shoes with thin socks, normally in the same tone as your suit and shoes. The socks should be long enough to cover the calf without the skin slipping out when you sit down. Don’t forget to give your shoes a quick polish before wearing them. If you have a belt, match it in tone with your shoes.
Not everyone has the privilege of wearing a suit every day, and a pair of black oxfords can be too formal.
Two good ways to vary are to go down a notch in shoe style, to a derby or fancy loafer, or to vary the color and material. A shoe in suede or brown leather, or with a brogue pattern, makes your outfit dressy without being overdressed.
In winter, for example, a pair of suede lace-up boots is a great choice, which goes well with jeans, sweatpants and chinos.
In everyday life
On the weekend, a pair of sneakers is a great choice. We have all the respect for those who geek out on modern designer sneakers, but for most men, a pair of minimalist white or leather sneakers is best. A more dressy option is a pair of loafers in, say, suede.
Socks are worn according to the season. In cold weather, wear socks – it just looks silly to go sockless then and you’ll feel silly walking around barefoot in someone’s home in December. In summer, use foot deoderant and forgo socks, or opt for a pair of no show socks .
On the beach
Nothing bad about sandals, it’s all about context. If you really want to go to the beach and swim, tolerable shoes like sandals and flip flops are a practical choice – they keep your feet cool and it’s easy to get the sand out.
But if you’re thinking about lunch at a nice restaurant by the beach, or a stroll through the shops, skip the sandals. Covered shoes such as loafers, moccasins, espadrilles, car shoes and sailing shoes are all shoe models that are cool enough but much more stylish. Canvas sneakers can work as an exception, but they will never be as stylish, and will get dirty quickly.
The history of men’s clothing
The age of sandals and moccasins
There is a certain irony in the fact that the shoes that some gentlemen today avoid are the ones with the most tradition: the sandals.
Exactly when and how humans started wearing shoes cannot be known for sure, as shoes were made of natural materials that degraded over the years. However, based on the anatomy of our feet, humans have been wearing simple shoes for tens of thousands of years.
The oldest sandals found are about 10,000 years old, made from wormwood fiber twisted into rope – much like a pair of espadrilles. 5,000 years ago, people in Armenia wore shoes made of stitched leather, stuffed with grass to provide some insulation. Today, these shoes would be called moccasins – they had no sole and consisted of a piece of skin folded around the foot and sewn together on the top.
In ancient times, civilization was dominated by cultures in warm countries, and therefore sandals predominated. In ancient Rome, a whole set of different models were developed for different purposes, from the military sandals caligae (what we sometimes call gladiatorial sandals) to the covered but ventilated leather shoes calcei .
Long, wide and high shoes in the Middle Ages
In the Middle Ages, the first guilds of shoemakers were created and the profession was very clearly regulated. In England, for example, a distinction was made between cordwainers (a corruption of Cordoba, which was known for making the best leather) making new shoes, and cobblers who repaired shoes.
Shoes were status symbols and shoemakers were not averse to adding to this. The Middle Ages saw a number of different eras of experimentation with the shape of the shoe, usually ending in curses and admonitions that ‘fashion has gone too far’.
Poulaines were pointed-toe shoes with phallic symbolism, which grew longer and longer until they became ridiculously and impractically long. Footbags were wide shoes, which began in the High Middle Ages, and which also became wider and wider. Due to the lack of hygiene and rubber boots, there was also much experimentation with different types of platform shoes, which could lift gentlemen and women above the dirt and mud of the streets.
Thanks to shoemakers, the design of the shoe also evolved. Originally shoes had been sewn inside-out, like a ballet shoe or moccasin, but now outsoles were sewn onto the upper, just like a modern shoe.
High-heeled shoes, knee boots and tights
When studying the history of shoes, it is clear that shoe fashion is anything but timeless. For long periods, men wore shoes that look more like modern women’s shoes than men’s shoes. Shoes were a status symbol, where impractical and beautifully decorated shoes showed that you were rich enough not to have to get dirty.
In the 16th century, the heeled shoe became the height of fashion. It was probably inspired by the Middle East, where men had been wearing heeled shoes for a long time in order to ride better. The original function of the heel was to keep the stirrup in place when riding. Heels were often combined with beautifully patterned tights.
It also became popular to decorate the shoes, with small ribbons, flowers and patterned fabric. Later, jeweled buckles became popular. So-called opera pumps , decorated low shoes sometimes worn with tuxedos, tails and other very formal occasions, are probably the only shoe model from this period that can be said to be still in use among men.
The boots were also high and would probably be more associated with women’s fashion today, although some boots were quite rough in material. Boots were mostly used for outdoor riding, and function was more important than form.
Elegant and ostentatious shoe fashion was at its height when Louis XIV pranced around in his high-heeled sandals with red heels. After the French Revolution, flashiness became a negative, and in England, early influencer Beau Brummel created a much more restrained men’s fashion.
19th century: The birth of the modern men’s shoe
Instead, the great wars of the 19th century focused on military fashion. Shoes became practical and durable. The leather had to be black and well-polished. Two influential models were the Blücher boot (a boot variant of what we call the derby) which with its open lacing was easy to pull on, and the Wellington boot, what we would now call a riding boot.
However, not everyone appreciated the long boots and soon the boots were shortened to the calf. One model was called the Oxonians or Oxford boot, because it was popular in the university town of Oxford, and would later give its name to the classic men’s shoe. oxfords . In the mid-19th century, the shoe models that would now be called men’s shoes were common, and a shoe from the latter half of the 19th century is almost identical to a well-made men’s shoe today. Fashions changed from pointed to square shapes on the toe.
The 19th century also saw major industrial advances. Singer, Blake and Goodyear invented machines that allowed for the industrialization of the production of edge-cut shoes. Shoes went from being made by hand by shoemakers to being made in large factories in places like Northampton, Brooklyn and Philadelphia. The shoes were then sold in shoe stores, requiring standardization of styles and sizes.
New materials at this time included suede, rubber and patent leather. Brogue patterns also became popular, inspired by Gaelic shoes with holes in them to allow moisture to drain away.
20th century: Shoe fashion reborn
In the 20th century, not much really happened in classic men’s shoes. A well-dressed man today could have borrowed a pair of shoes worn by an early 20th century gentleman without anyone reacting (except possibly to the excellent craftsmanship).
The 20th century was above all the era of shoe fashion. Several new models such as monk’s shoes, Chelsea boots and the two-color co-respondents were created by inventive marketers. Casual shoes like espadrilles and sandals became fashionable as a healthy and active lifestyle became the new ideal. Boots went from being a standard for men to something rebellious, as surplus stocks sold off old military equipment after World War II.
Already in the 19th century, men’s and women’s shoes had begun to differ greatly, and in the 20th century the trend was completely different. Women’s shoes were heavily influenced by fashion designers such as Dior and Ferragamo, while men’s shoes remained more conservative.
2000s: The era of the sneaker
Perhaps the biggest shift in men’s footwear in 200 years took place at the end of the 20th century. The sneaker had already been invented in the late 19th century, but originally they were shoes for exercise and nothing else.
Only in the 1970s did clever marketers like Nike and Adidas figure out how to position the shoe as a lifestyle product instead, and artists and athletes became the new fashion icons. In the 90s, sneakers really took off, thanks in no small part to basketball and its connection to music. Nike’s collaboration with Michael Jordan and Adidas’ collaboration with runDMC are examples of how they actively worked to reposition the sneaker as a new status symbol.
In the 2000s, sneaker brands started collaborating with fashion designers. Shoe-collecting sneakerheads, exclusive model releases and social media created a unique subculture around a single shoe model. Even classic men’s brands slowly adapted, and started making high quality leather sneakers to complement their traditional shoe models,
The sneaker is arguably the biggest thing to happen to men’s footwear in nearly 200 years, whether you like it or not. Will they continue their winning streak in the man’s wardrobe?