The Best Dress Shoes for Men: Learn What Are The Most Stylish Types of Shoes Every Gentleman Should Wear 

The top rule of a men’s style guide is that dress shoes are the pièce de résistance of a gentleman’s attire. No matter how great the outfit, a bad shoe choice could completely ruin your dapper look. Fortunately, it won’t be the case if you stick to this best men dress shoe guide for 2019.

What are you first looking at when buying a new pair? Do you need super comfortable dress shoes? Or maybe a colourful model to match your bright personality? Is there a special occasion that demands stylish dress shoes? What is the first thing you consider when choosing them? 

Whether you’re looking for your first leather shoes for men this year or want to upgrade your dressing with a new high-quality pair, Tudor Tailor’s Dress Shoe Guide is here to help you make a dapper decision, fit for your dapper style.

Take a look at Tudor Tailor’s tailored dress shoes collection and choose your favorite pair to match your style.

Men shoes dressing

To be honest, you can really tell a lot about a person by their shoes: their style, their personality, if they’re an extrovert or introvert or if they’re agreeable people or not. For example, a worn-out pair of dress shoes is not necessarily cool or vintage-like. Especially if they look dowdy, this may suggest a person who doesn’t care too much about their looks. 

But a pair of polished Oxfords are the business card of a gentleman who knows how to make a memorable impression. 

Whether you own the best stylish shoes for men or the most expensive ones, it’s not all about looks. Price or brand doesn’t matter too much, as long as you stick to high-quality care of your appearance. 

You should feel great in your own leather shoes (!) that match your style and this will surely reflect in your positive encounters. And, yes, you can do that with some cool men’s shoes that don’t cost a fortune!         

Now, let’s see what timeless shoes a gentleman should find in his dressing in 2019 - and the next couple of years. Here are the best types of stylish men’s dress shoes:

Types of Elegant Men’s Dress Shoes 

Oxford Dress Shoes

As you may know already, these ones are the most popular men’s dress shoes in the world, just like the Derby styles. So, if it’s your first and possibly only a pair of elegant shoes ever, go for this one.

The Oxford type is a laced shoe that has the leather sides seamed. The sides of the shoes are sewn under the toe cap and, when closed, they slightly merge forming the V letter towards the tongue.

Oxford shoes are indeed more formal and rigid than other types, but comfortable enough to feel great in them for a special evening or a black-tie event. 

Where to wear men’s Oxford shoes: Their elegant look recommends them for special occasions such as weddings, baptisms or any special event. 

How to wear men’s Oxford shoes: They fit well into the modern men’s shoe types because of their versatility, leather types and colour palette, which are great for smart casual outfits. But the perfect match for Oxfords remains the elegant attire and the office look.

And there are several types of Oxfords as well, depending on the leather, toe cap and design:

Cap Toe Oxford Shoes

This elegant dress shoe model has an extra leather piece on the front side. The Cap Toe Oxford is known as the most formal type of all top men’s dress shoes and is perfectly crafted for the sharp businessman. The main advantage of this refined type of men’s shoes is that it hides a part of the creases that form over time due to constant wear.

Where to wear men’s Cap Toe Oxford shoes: a pair of black leather Oxfords can be worn at the office, but also at a formal reception or at a wedding. After all, it’s a classic in every gentleman’s wardrobe. Also, for ceremony outfits, these ones are the best black dress shoes you can wear, while brown Oxfords are better suited to more casual combinations with blazers, tweed or even casual jackets.

How to wear men’s Cap Toe Oxford shoes: If you want to wear a pair of black Cap Toe Oxford shoes to a suit, do not choose a brown suit. Black shoes fit best with a dark-coloured suit in navy, grey charcoal or light grey tones.

Wingtip Oxford Shoes

This style of Oxford dress shoes has a rounded toe cap and often enough, a pattern of decorative perforations called brogues on the sides and cap toe. If you are looking for the perfect pair of stylish casual shoes, the Wingtip Oxford is the one for you. They are much more suitable for casual wear than for formal wear.

Brown Wingtip Oxfords are ideal for elegant suits for day events.

Where to wear men’s Wingtip Oxford shoes: They go extremely well with a pair of Chino trousers or denim jeans, but they can also complete an elegant or formal outfit if you have the right suit for the occasion.

How to wear men’s Wingtip Oxford shoes: If you want to add more personality, opt for the best brown dress shoes for your smart style. They’re the most popular choice for a modern classic look that makes you stand out in the crowd. Wingtip Oxford shoes work perfectly with a clean suit; just try to lean towards earthy shades such as beige, khaki or brown.

Whole Cut Oxford Shoes

This is definitely the luxurious style that is meant for truly special occasions. Made from a single piece of leather with or without brogues, but with no cuts or other extra decorative details, the Whole Cut Oxford is a higher-quality shoe (the manufacturing process is more demanding for this type) and a must-have pair for the classic, refined gentleman.

Moreover, the closed eyelet section (Oxford laces) adds an even more formal, sleek touch to your outfit. 

Where to wear men’s Whole Cut Oxford shoes: The Oxford Whole Cut Shoes are the best dress shoes of the moment. They complete a flawless gentleman look for any formal event: a black-tie party, a wedding ceremony. You can wear them at your own wedding, as well.   

How to wear men’s Whole Cut Oxford shoes: Being a highly refined and elegant type, Whole Cut is one of the best formal shoes you can choose for an outstanding formal outfit, and this is why is best to choose your clothing items wisely. Wear them with business suits or ceremony suits. 

You can opt for something different in your wardrobe, this year: a pair of oxblood shoes (burgundy coloured shoes) will fit incredibly well with navy, dark grey or light grey suits. Such cool dress shoes are all you need for a distinctive, masculine look.

Plain Toe Oxford Shoes 

This last type of dress shoes for men, the Plain Toe Oxford, is definitely THE pair you should own. They perfectly illustrate the "less is more" principle, which is increasingly popular when talking about masculine style - because simplicity often defines elegance and a refined taste.

Being such a popular model among the best formal dress shoes for men, you can find them at various prices. However, if you want guaranteed quality and longevity of the product, invest in an Oxford shoe made of top quality leather.

Where to wear men’s Plain Toe Oxford shoes: it is the "cleanest" dress shoe for men, with its unlined and simple cap toe. You can always rely on such a pair of lacquered shoes. They’re the go-to choice for black-tie events, ceremonies, a ballroom event or other exquisite events.  

How to wear men’s Plain Toe Oxford shoes: being the most elegant Oxford style, they are the best formal dress shoes for sophisticated attire: tuxedos, black-tie suits, ceremonial suits in general. 

If you want to see the best dress shoes for men in 2019, suitable for stylish and business or casual wear, see our entire collection of gentlemen’s shoes for any occasion

Types of Business Men’s Shoes

Derby Shoes

Derby Shoes have laces and their quarters’ facings are not sewn and lay on top of the vamp, unlike Oxfords. If you were looking for comfortable stylish walking shoes, a Derby pair is definitely for you.

Derby shoes are also ideal for men who have wide feet since the sides of the shoe don’t touch and you can adjust how tight or relaxed the shoe is.

Best Derby Shoes for men


Where to wear men’s Derby shoes: they are versatile shoes that can easily complete a three-piece suit, but also a casual outfit consisting of a pair of Chino trousers and a jacket. These shoes are mainly recommended for formal meetings and events.

How to wear men’s Derby shoes: they are the perfect choice for the modern business gentleman with a schedule so busy he doesn’t have too much time to think about the next day's outfit.

Plain Toe Derby Shoes

Derby Plain Toe is a classic shoe type, which has no model on the front (cap toe). They can be worn both in formal or casual wear and in everyday wear by gentlemen working in the business environment.

They are the ideal pair of office shoes for men, especially for those who are not professionally obliged to wear more elegant, stylish shoes like the Oxford model.

Types of Casual Dress Shoes for Men

Brogue Shoes

If you’re wondering about the most stylish casual shoes for men in 2019: the Brogues. They have various decorative patterns and details on them, made through a perforating technique. 

Long ago, these perforations on the surface of the shoe were meant to allow water to enter and exit the shoe. Irish farmers, who did not want to bring all the water into the house after working in gardens and farms, adopted this type of shoe.

The term "brogue" originates from the Welsh word "brog" meaning shoe. Brogue shoes are also called "Budapest" shoes because in Hungary there are some of the best shoes of this kind.

Full Brogue Shoes

Full Brogue shoes have a perforated pattern that resembles wings and extends over the entire side surface of the shoe. Many people consider this type the most iconic gentleman shoe style, one that will never fade.  

Where to wear Full Brogue shoes for men: surely they are not suitable for a black-tie event but are the perfect footwear for tweed or country fabrics for stylish casual attire.

How to wear Full Brogue shoes for men: this model should not miss from any gentleman’s wardrobe. It's an extremely versatile shoe that can be worn in informal wear, especially if you have it in a classic cognac, chestnut or chocolate colour.

Semi-Brogue Shoes     

This style is more subtle, yet distinctive than the previous Brogues because it only has perforations at the base of the cap toe and on the shoe tip. They are preferred by gentlemen with a more business casual style, keen on the Italian refinement.  

Where to wear Semi Brogue shoes: being the casual, yet fashionable choice for business casual attire, you can wear them at business events or meetings, as part of your daily style.  

How to wear Semi Brogue shoes: They fit with soft materials such as flannel, but also with suits in delicate prints (such as the plaid or checkered Prince of Wales print). Combine these stylish casual shoes for men with suits in earthly, navy or light grey tones for a smart chromatic effect.

Quarter Brogue Shoes

As their name suggests, the Quarter Brogues have the simplest perforated pattern, they're only decorated at the base of the cap toe or on the tip of it.

Where to wear Quarter Brogue shoes: if you want to wear Brogues with a formal suit, go with Quarter Brogues. Their subtle details will make the difference in style. They are also a wonderful choice for business attire because of much fewer decorative broguing perforations than on the Full Brogue.     

How to wear Quarter Brogue shoes: This type of casual leather shoes will add sophistication to blue and grey business suits, as well as the more elegant, formal ones. 

Monk Shoes

Their style particularity is the monk strap, which makes them the “most advanced” dress shoes for men. Although Monk shoes have been in the spotlight for twenty years already, they are still viewed as a fashion statement in the world’s men’s style trends.

In terms of construction, Monk shoes are a combination of other types of dress shoes. They're slip-on style like the Loafers, but have the tongue and cap toe similar to the Oxford model. 

Because Monk shoes don’t have a culture on their own,  they’re hardly “accepted” in men’s wardrobe. But this very aspect makes them special for the powerful gentleman: Monk shoes are the elegant way of getting out of the comfort zone - in style.   


Where to wear Monk shoes: The traditional laces have been replaced with one or two straps (or sometimes three!) that cross the shoe surface, which makes them so versatile they can be worn with denim clothing for a brunch or a casual evening, but also with the most formal outfit for a high-class business event.

How to wear Monk shoes: they belong to the modern gentleman who wants to be noticed for his exquisite taste and maybe eccentric personality, at the cross between classic and contemporary. 

Double Monk Galahad Shoes The Double-Monk Patina Galahad shoes are the perfect choice for gentlemen who want to highlight their style in society. You can customize and order them here. 

Single Strap Monk Shoes

The Monk shoes with one strap only are more classic than those with two straps and they also do not attract the attention that much. Even though are not as popular as the latter, they will give you a nonconformist yet neat, elegant look.

This doesn't mean you can't make a powerful statement with a pair of Single-monk Shoes. Especially when they come in seductive nuances and patina finishes that make this type of shoe a truly elegant one. 

unique Monkstraps for the powerful gentleman Single-Monk Purple Patina shoes, the Baudwin shoes are distinguished by a special elegance, which is attributed to the seductive purple hand made patina. You can order them here.


Where to wear Single Strap Monk shoes: they are not conventional enough to go well with suits for black tie or business events with strict dress codes. But you can wear them at the office or with a more casual outfit for a confident, dapper look at a romantic date or a relaxed social event. If you want to make a statement, choose a pair in a subtle nuance with patina finishes that speak about a truly powerful, elegant gentleman.    

How to wear Single Strap Monk shoes: they work great with anything but formal suits. Choose brown shoes for most of the outfits, and burgundy tones for blue suits or clothing. This type of monk shoe is recommended for elegant outfits from the seduction of subtle nuances associated with powerful people.

Double Strap Monk Shoes

As for the Double Strap Monk shoes, you have much more versatility than you think. They are more popular than Single Strap and are worn by young people or fashion-savvy gentlemen who are not afraid to be the centre of attention.   


Where to wear Double Strap Monk shoes: You can wear them in any setting, especially at parties or networking events or when you go out or at a romantic dinner. 

How to wear Double Strap Monk shoes: Choose brown Double Strap Monk shoes for a clean, relaxed look, or burgundy Monks for blue or denim outfits or black ones for classic pieces that never go out of style. Opt for business casual suits or in combination with a white shirt, Chino trousers, and a cardigan.

Loafers Shoes 

Loafers are a type of shoe without laces. Besides, they are slip-on, which makes them extremely comfortable and easy to wear. They work well with different smart casual outfits. 

Loafers are the most representative for casual men's shoes, and that is why they are not as elegant as the other types. However, being extremely versatile, they can complete a gentleman’s costume in a stylish way.

Everything has its own story, and Loafers are no exception. When King George VI decided that he wanted shoes for the interior of his house, his shoemakers created the first pair of Loafers shoes. Although they were designed to be worn inside, they soon became an outdoor shoe ideal for those standing on their feet all day.

The first aspect you need to consider when choosing a pair of Loafers is the leather which you want the shoe to be made from. The most sought after materials for this type of shoe are the normal calfskin, or Suede (made from deerskin).

Normal leather Loafers are more durable than those made of Suede, making them a pair worth investing in because you can enjoy their style and comfort for a long time.

Suede Loafers are a bit more pretentious and require much more care. They are regarded as summer shoes for men, so wear them exclusively in the warm season to keep them away from moisture.

colored suede loafers for men

In terms of style, Suede Loafer shoes have more casual air than those in normal calfskin, so they fit best with light casual clothing.

Penny Loafers

This type is the most classic Loafer model. They have no decorative details, such as fine tassels or other beautiful applications. Being a footwear classic, you can pair them with other classic clothing - jeans, bomber jackets. 

Loafer shoes with blue suit for men Penny Loafers are simple, comfortable and elegant. Choose a dapper gentleman look with a brown Suede pair and a blue fashion ensemble.

Where to wear Penny Loafers shoes: Being a minimalist and versatile type of dress shoe, they work great in day outfits, no matter the season, for a whole range of occasions - for interviews and business meetings, but also for day parties, romantic dates or social gatherings. 

How to wear Penny Loafers shoes: if you’re looking for stylish shoes for men to wear with your favourite pair of jeans, Penny Loafers are your best choice. They are extremely versatile and come in many refined models, so you can wear them with denim, Chino trousers or any casual suit.

Tassel Loafers

As the name suggests, they do have a tassel detail in their construction. Tassel Loafers distinguish from the classic, refined Penny Loafers with their tassels placed on the leather band that crosses the shoe. 

They were inspired by the design of the boat shoes, which have a lace passing through 2-3 eyelets in and out of their sides, which ties on top of the shoe. Usually, men wear this type of footwear with short trousers for a cool gentleman’s summer look. 

Where to wear Tassel Loafers shoes: being a perfect choice for summertime outfits, these comfortable stylish boat shoes for men will give you a relaxed, modern look for summer parties and holidays, a beautiful walk in the city, or relaxing aboard the boat deck.    

How to wear Tassel Loafers shoes: choose traditional colours for a smart casual outfit, or, if you like to experiment, go for bold models and colours to ensure an up-to-date, sharper, cooler look. Add a bomber jacket, a blazer, and Chinos trousers or smart jeans and you’re ready to go.   

Black elegant loafers for men Loafers are made to offer you extra comfort, while in the same time maintaining an elegant look. You can order them here. 

Bit Loafers

They became popular because of so many major fashion houses praising and promoting them continuously. The Bit Loafers model is recognized by a metallic detail placed on the top of the shoe (throat line). This precious detail makes them fit for an elegant gentleman that has a simple and relaxed look. 

Where to wear Bit Loafers shoes: Being a bit more elegant than the other Loafers, you can wear them at more stylish or formal events, not just on casual occasions. 

How to wear Bit Loafers shoes: A pair of Black Bit Loafers shoes are stylish enough to wear with a suit, but they are not formal enough to be included in a black tie or white tie outfit.

There are gentlemen who have a dilemma when it comes to the socks they have to wear with their footwear, especially with the dress shoes. If you are in such a difficulty, it’s useful to know that there are some etiquette rules that you can guide after.

Which Stockings Should You Choose for Elegant Dress Shoes?

In formal or business environments, socks should always be part of your outfit. Moreover, they must be long enough to cover your ankle even when you cross your legs.

Fashion advisers also recommend that you match your stockings with your trousers, but not with your shoes. The stockings should be a visual extension of the trouser, so it is not advisable to choose a colour that makes a discordant note.

If you want to compliment a relaxed look, you can choose to wear stockings with various patterns and textures. Go for shades that balance the rest of your outfit, for a charming masculine look.

stockings to wear with elegant dress shoes for gentleman

Never wear white stockings with a pair of stylish dress shoes. They only make the entire fashion ensemble look cheap and boring. The biggest stylistic faux-pas that you can do is wearing a pair of black trousers with black shoes and white stockings.

The situations in which you can wear elegant sockless shoes are quite rare. Being more casual footwear, the Loafer shoe is the easiest to wear without socks on sunny summer days.

Even in these situations, Tudor Tailor clothing consultants recommend that you wear a pair of socks to prevent shoe damage.

How to Extend the Life of Your Shoes

A pair of high-quality dress shoes can be a pretty big investment, so you'll most likely want to enjoy them as much as possible. How do you take care of your shoes so they can last a lifetime?

To make sure your favourite pairs keep their shape, store them with wood shoe trees inside. The cedar wood shoe trees especially will not only keep your elegant footwear in their proper shape but will also absorb moisture and unpleasant odours. They are most needed for natural leather shoes, which are harder to maintain than those made with ecological leather.

Now that you know what types of men's shoes should have their special place in your wardrobe and how you should match them correctly, you can easily create elegant outfits that tell the story of a true gentleman.

Choose the model that matches your personal style or send us your measurements to create the new pair of stylish dress shoes tailored to your size and taste.

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