Your Guide to Men’s Dress Shoes | Curated Mint

They say “walk a mile in my shoes”, but which shoes are they talking about? Check out our complete guide to the different types of men’s formal shoes alongside when, and how, to wear them.


A tailored suit, fresh shirt, a tie that matches your handkerchief, a pair of ravishing cufflinks…it seems like you’ve got it all covered from head to well, ankle because there is one thing missing: a great pair of formal shoes.

A versatile pair of formal shoes is something each man should have in their wardrobe, there will always be an occasion. If not, there are many ways you can dress them down for day to day wear. But how do you choose the style? How do you know the colour? Will they be comfortable? There seems to be a lot of pressure when it comes to shoes, the expectation is to get them spot on.

The design of men’s dress shoes is centuries old, and over those centuries these shoes have been building up a sort of persona if you like, a certain feel to them. Despite starting off as a smart university option look for the young, and an everyday sophisticated look for the older man, the formal shoe has been paired with some pretty extreme outfits over the years.

Types of Men’s Dress Shoes

In general, there are seven types of formal dress shoes out there:

  • The Oxford
  • The Blucher shoe
  • The Monk Strap
  • The Loafers
  • The Desert Boot
  • The Chelsea Boot
  • The Opera Pump

Whether picking a pair from a store, or your own wardrobe you need to consider the occasion that you’ll be attending and the rest of your outfit. Fashion equals freedom of expression, however, we don’t want to cross the line because there are some rules that just shouldn’t be broken. For instance, do no wear brown shoes with a black suit, just don’t do it.

Try not to be too overwhelmed by the multitude of options available. There are pros and cons to each style meaning, the more you have – the more you’ll be ready for any situation. If you play your cards right, you will definitely stand out with the most dashing getup possible.

black loafers for men

Just remember that being an expert in men’s shoes bumps you up to a new level of style. In the shops, the comfort seems to be the priority, but as I got older, it appears that there is a certain art to it.

Entering the world of the Formal Shoe is like getting into an elite club. Maybe not for everyone, but it’s a surefire way to earn some style points. Sorry to disappoint, but there is no ceremony. What you do get is a slight nod from the cashier when you purchase a pair or a slight smile of admiration from someone sitting opposite you on the train as they just admired a pair of your Oxfords.

The Oxford Shoe

Not only do Oxford shoes scream sophistication and class but they also will become your best friend if you start a job in an office or attend several formal events. The trick with these shoes is to choose a pair wisely in terms of comfort. You really don’t want to be that guy smiling through the pain.

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To identify a pair of Oxford shoes, you really need to look at the toe, as the shoes get gradually narrower closer to the point and finish with a blunt pointed front. The laces are rather small and you might find some detail in the stitching. The colour of the leather may also vary from one end of the shoe to the other. However, all these characteristics can be chosen according to taste.

Whilst you have your fun choosing the colour and detail of your Oxford shoe, you need to make sure you know how to lace them properly. Do not think of it as restriction of your freedom, look at it as a tradition of the shoe.

It’s important to make sure the toes aren’t too squished together with an Oxford shoe, so always allow room for your socks. Although, there is a trick when it comes to shoes like Oxfords. When buying a pair, they might be slightly uncomfortable and they might rub. However, once you break them in – they will last you for years.

So the trick is to break in your shoes and then over some time just re-sole them and bam you’re sorted.

mens black oxford shoes

What to Wear with Oxford Shoes?

The million-dollar question. Oxford shoes originated in Oxford University where male students maintained their sophisticated and smart style with a pair of brown Oxfords. While the ‘proper’ way to wear the Oxford shoe requires maintaining that smart style, you can experiment with your outfit as many other men do in the current day.

As shown below, some treat the Oxford shoe as strictly office gear. Remember when you are pairing a suit to go with your shoes, the biggest mistake one could make is a black suit with brown shoes. A pair of brown Oxford shoes works well with a navy suit or lighter and darker shades of grey.

If you are looking to pair Oxford shoes with a more casual office outfit, instead of a shirt under your suit you could wear a turtleneck as shown in the picture below.

The Blucher Shoe

For those of you who are looking for something with a twist to add some flare to your outfit, the Blucher shoe might just be for you. They’re really similar with Oxfords because of the shape, but they are a little more round and curvy.

The Oxford is more minimalistic, it has subtle detail and sharp edges it’s serious and sophisticated. The Blucher shoe has more detail and it’s much more textured, it steals the show so you should wear it with subtly patterned suits and you can rock it on a day-to-day basis.

Just like the Oxford shoe, this pair is something you could style with a suit. Also, because of the tough leather and the detailing, it would look better if the suit features a subtle pattern.

blucher shoe gentlemansgazette

The Monk Strap

These are a nice middle ground between the two shoes above, The Oxford and The Blucher Shoe. The Monk Strap are traditionally made for smart gatherings and important events and instead of laces, they have a strap/buckle that secures the shoe. Despite their chic persona, some have put a real rock spin on the shoe and embraced the metal strap with leather jackets and wide brim hats.

The safest way to rock The Monk Strap shoe is with classic outfits, a plain blue shirt, three-quarter length trousers and a watch to complete the look like shown below.

mens monk strap shoes grey suit street style

The Loafer Shoe

Loafers, or slip-ons, are much more suited for a casual setting. They are perfect to be styled with rolled up trousers or jeans and depending on the colour, dark or light, a shirt or a plain T-shirt.

But as we’ve said before fashion is a form of expression, so you do what you’ve got to do. Despite having a formal look to them, loafers have a feel of luxurious leisure when styled with chinos, an opened shirt and some sunglasses.

Modern catwalks push the boundaries of what to wear with what on a daily basis, so if you want to wear a pair of loafers with some socks and some rolled up patterned trousers – we’re giving you the green light.

loafers for men

Dessert boots, also known as Chukka Boots, were brought into the fashion world by British forces. In fact, the military influence on men’s footwear is evident throughout fashion and footwear through the years. In the 20s and 40s, people were glorifying soldiers and their efforts in protecting their country. As a result, certain parts of the uniform that they once wore in the battlefield or on mission became their everyday wear.

It’s for this reason that The Desert Boot is something that is not entirely casual but isn’t smart either. They demonstrate some sort of authority that a soldier would have but then they are comfortable and stylish to wear with your jeans or chinos.

To identify a desert boot you need to feel the material, the majority of desert boots are made of suede. This means that, as soon as you’ve purchased a pair, it’s a good idea to spray some suede protector on to make them rain-suited.

Desert boots are secured with a short lace on the top just above the ankle, because of their height, they usually work with skinny trousers that come down to a few centimetres above your ankles or rolled up jeans.

When looking at what to wear them with you need to look at the colour because lately, shoemakers have begun to experiment with the dye. The darker and fuller colours are made for serious events where you have to look smart. For example, a dark brown desert boot is perfect for pairing with a tweed suit for meetings or office work.

mensstylefashion desert boots

The Chelsea Boot

These are easily one of the most popular formal shoes out there, not only are they sleek and classy but they have a great history to them that just screams Britain. Their original design is rooted in the 1800s, when Queen Victoria’s shoemaker, J. Sparkes-Hall made a pair of what today would be called Chelsea boots for the Queen and stated that:

She [Queen Victoria] walks in them daily and thus gives the strongest proof of the value she attaches to the invention.

– J. Sparkes-Hall

Although some might say that that was simply a marketing trick, the design clearly worked. It stuck in the British fashion industry for centuries, surviving both World Wars and becoming the rock’n’roll symbol in the 50s and the 60s.

Although maybe today the Chelsea boot is associated with Dr. Martens and a more of a punk or grunge scene, only a few decades ago they were a key to many of The Beatles outfits. Rumour has it, that John Lennon and Paul McCartney saw a pair of pointed Chelsea boots in a vintage shop and requested a similar pair. The style soon caught on and the iconic Chelsea boot was worn not only with jeans and leather jackets but also suits as modelled by The Beatles below.

the beatles chelsea boot gentlemans gazette

Despite the shoes being worn by both men and women, the style of the shoe is undoubtedly chunky and very masculine. They are usually made of thick leather, which makes them suitable for any weather, especially rainy England.

Chelsea boots look really good with all the typical English clothing such as Harrington jackets or Fred Perry polo shirts. When choosing a pair of Chelsea boots make sure to check the quality of the leather and, we’re warning you now: they will hurt at first, blisters are a part of the experience.

Once you have broken them in, and they have finally accepted the shape of your foot – they will be the most comfortable pair of shoes you own. In terms of looking after them, all you’ve got do is polish them and wash the dirt away.

Chelsea boots are a good investment for those who like that typical rock’n’roll style, but also for those who wear suits on a daily basis as the Chelsea boot does look very smart with some tailoring. They’re not the best summer option, but they are great for the other three seasons.

the beatles chelsea boot gentlemansgazette

The Opera Pump

The final shoe we have for you can easily be considered the royalty of all men’s footwear. They are formal but on a new level. These shoes not only look like they were worn by the King of France at some point, but also the heel will give your walk that sound that will tell people you’ve invested in some seriously well-made footwear.

photo credit: google | shop: shoes

In terms of where to wear them, the Opera Pump is self-explanatory. However, if you have another occasion where ultra-formal is the required dress code, you might want to purchase a pair. The only suitable pairing for Opera shoes is suiting, you might have the urge to cross the line and wear them with a funky outfit – but it won’t look great. Put on a pair of silk socks, a three piece and a bow tie, gel your hair back and stroll with your head held up high.

Types of Dress Shoes

  • The Oxford: the most versatile, and ultimate choice when it comes to formal footwear.
  • The Blucher shoe: it has more subtle detailing and sharp edges making it a serious and sophisticated option.
  • The Monk Strap: a nice middle ground between the two shoes above, can be dressed up or down depending on the event.
  • The Loafers: much more suited for a casual setting. Perfect to be styled with rolled up trousers or jeans.
  • The Desert Boot: marginally more casual, alternative to formal footwear and can be paired with both suiting and more casual trousers.
  • The Chelsea Boot: quintessentially British, can easily adapt to both casual and formal settings depending on the style and material.
  • The Opera Pump: appropriate for ultra-formal occasions.

mens dress shoes flat outfit

On That Note

As you can see, the world of formal footwear is not all that scary. You just need to be aware of the different styles and the occasions they’re suited to. Now that you are an expert in men’s formal shoes you can put on your dancing shoes and go paint the town red.

Feature image from Pinterest

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