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Men's Shoe Guide: Shoe Styles Every Gentleman Should Own

Whether you're looking for your first pair of men's leather shoes, or you want to complete your wardrobe with a new pair but don't know what you're missing, Tudor Tailor's guide to men's shoes and boots is meant to answer all your questions.

Discover the Tudor Tailor men's footwear collection and choose the pair of shoes that suits your style!

Footwear says a lot about the style you want to approach, but also about your personality. A person can tell certain traits of the wearer's behavior just by observing the shoes.

A worn and unkempt shoe denotes an individual who doesn't put much value on his attire. In contrast, a pair of polished Oxford shoes are the calling card of a gentleman who knows that dress code is important when you want to make a memorable impression.

Here are the types of shoes that should not be missing from an elegant gentleman's wardrobe:

Elegant men's shoes

Stylish boots for men

We chose to start with an important footwear model that is important to have and wear, especially for typical cold season outfits: a pair of men's fall-winter boots .

Boots made of 100% natural leather, like the full-brogue Derby model below, are essential not only for maximum comfort during cold days when you have to work in the city, but they also look very elegant in both business outfits and smart casual transitional outfits for the fall-winter season.

Elegant Jodhpur boots

This style is a little-known one, but extremely versatile and elegant for gentlemen - but it all depends on the accessorizing. There are several types of boots for men, and this jodhpur model refers to the buckled boot, slightly higher than the usual ones, which was usually worn for horseback riding.

Men's jodhpur boots are made of fine, quality leather, and look very classy with chinos or even jeans. But they can also look great with formal outfits, not just elegant casual. What makes them special is the fact that they are ideal in the cold season, when you need comfortable and durable footwear for the conditions outside - ice, snow, rain. This model of boots has a special sole to give you safety, not just a special style.

Oxford shoes

Oxford shoes for men are among the most popular men's shoe styles, along with Derby shoes.

See the entire selection of men's Oxford shoes, Tudor Tailor brand.

An Oxford is a lace-up shoe characterized by having the toes sewn in. The sides of the Oxford shoe are sewn under the vamp, and when closed they come together slightly, forming a V towards the tip of the shoe's tongue.

Oxford shoes are ideal for special occasions such as a wedding, christening or special event. They are stiff and formal, but still comfortable.

Although they are very versatile and can also be worn with smart casual outfits, they are best suited to elegant or office attire.

Cap Toe Oxford Shoes

The Oxford Cap Toe model has an extra piece of leather that crosses the front of the shoe. The Oxford Cap Toe is the most formal of men's shoes and represents the specific image of the man well-grounded in the business world.

The advantage of the Cap Toe model is that it hides some of the creases that form over time due to wear.

Black Oxford shoes for men can be worn to the office, but also to a formal reception or a wedding. A pair of black Oxford shoes for men is an ideal choice for formal attire, but brown Oxford shoes are also suitable for more casual combinations, with pieces such as blazers, tweed jackets or even casual sports jackets.

If you want to wear a pair of Black Cap Toe Oxford shoes with a men's suit , don't choose a brown suit. Black shoes look best with a black, navy, charcoal or light gray suit.

Wingtip Oxford Shoes

Wingtip Oxfords have a rounded toe and are often perforated in a brogue style. They are a beautiful pair of shoes, more suitable for casual wear than formal wear.

They go great with a pair of chinos, a pair of denim jeans, but also with a suit, when the frame is right.

If you want to wear a pair of brown Wingtip Oxford shoes with a suit, keep in mind that they go best with suits in earthy tones, such as beige, khaki, or brown.

Whole Cut Oxford Shoes

Made from a single piece of leather, without cuts or other additions, Whole Cut Oxford shoes have a luxurious feel. Ideal as men's wedding shoes, you can wear them to any type of special event, even your own wedding.

They are shoes that are suitable for formal occasions, but also shoes that you can walk in with confidence while heading to the office. They are very elegant, so choose carefully the clothing pieces you want to match them with. They go best with business suits or ceremonial suits .

Cherry red shoes for men, in the Oxford Whole Cut style, harmonize chromatically with navy blue, charcoal gray, or light gray suits.

Plain Toe Oxford Shoes

Plain Toe Oxfords are a pair of shoes for elegant men. They illustrate the principle of “less is more”, which is increasingly popular in men's style - simplicity often defines elegance.

The Oxford Plain Toe model is the “cleanest” shoe, with an unadorned front. You can confidently wear such a pair of patent leather men's shoes, especially at formal events.

Being such a popular style, you can find men's Oxford shoes at a variety of prices, from low to high. However, if you want to be sure of the quality and longevity of the product, invest in an Oxford shoe made of the highest quality leather.

Men's business shoes

Derby shoes

Derby shoes are lace-up shoes, characterized by having seamless uppers. They are very comfortable, ideal for gentlemen with wider feet. The side pieces of the shoe do not touch, which provides more comfort to the wearer.

They are versatile shoes that can be easily matched with both a three-piece suit and a more casual outfit, consisting of a pair of chinos and a jacket.

Men's Derby shoes are the perfect choice for the modern gentleman, with an extremely busy schedule that doesn't allow him to think about his outfit for the next day.

Plain Toe Derby Shoes

Plain Toe Derbys are a classic type of shoe that has no pattern on the front. They can be worn with both formal and casual attire, as well as everyday attire, by gentlemen who work in a business environment.

They are the ideal pair of office shoes for men, especially for those who are not professionally constrained to wear elegant shoes, such as the Oxford model.

Men's casual shoes

Suede boots

In the case of smart casual daytime outfits, for the colder season, play it safe with an iconic model that won't go out of style anytime soon: suede boots.

Men's suede boots, especially chukkas, are a timeless classic, perfect for the fall or spring season. Wear these suede boots in modern colors, like navy blue, with jeans or a pair of chinos for a comfortable and versatile style.

Military boots

This model is unconventional and extremely in fashion this season. Also called combat boots or military boots, these winter boots for men with a military look are far from being pretentious, on the contrary - such a pair of shoes is a must-have for men who prefer a special touch in their non-conformist style, thanks to the edgy accents and versatility in modern casual and smart casual outfits.

Choose a pair of military boots in a subtle color like olive, along with a pair of dark jeans or slim pants and a stylish men's coat, in your wardrobe for the cold season.

Not only do they guarantee comfort and safety with every step, but these men's boots are ideal for adrenaline-filled days, mountain getaways, and remarkable appearances at a fashionable party.

Brogue Shoes

Brogue shoes for men are those shoes that have various patterns and decorative details, made using the perforation 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 didn't want to bring all that water into the house after working in their gardens and farms, adopted this type of shoe.

The term “brogue” comes from the Welsh word “brog” which means shoe. Brogues are also called “Budapest” shoes, because Hungary produces some of the best brogues.

Full Brogue Shoes

Full Brogue shoes have a perforated pattern that resembles a wing and that extends across the entire lateral surface of the shoe.

This model should not be missing from any man's wardrobe. It is an extremely versatile shoe that can be worn with informal outfits, especially if you have it in a classic shade of cognac, chestnut or chocolate.

Semi Brogue Shoes

The Semi Brogue model is more subtle than the Full Brogue model and is characterized by the application of perforations at the base of the seam on the head toe, as well as a perforated pattern on the toe of the shoe.

They go well with soft fabrics like flannel, but also with suits with delicate prints like Prince of Wales checks. Pair them with suits in earthy, navy or light grey tones for a striking chromatic ensemble.

Quarter Brogue Shoes

Quarter Brogue shoes have the simplest perforated pattern, thus being decorated only at the base of the cap toe seam or on the tip of the shoe.

The Quarter Brogue is a good choice for business or formal wear, as it is not as detailed as the Full Brogue. Wear this type of shoe with business or elegant suits in shades of gray or navy.

Monk shoes

Monk strap shoes have been making a comeback in the spotlight for about 20 years now. This type of shoe is a bold move in the world of men's fashion and style.

It doesn't have a very broad culture and isn't accepted by all men, precisely because it's a model that steps out of the comfort zone.

They are the mark of a modern gentleman who wants to stand out through his footwear. They are shoes that represent a mix between classic and contemporary, with a characteristic touch that gives them an extra touch of personality.

In terms of construction, Monk shoes are a combination of an Oxford shoe and a Loafer shoe. They are slip-on style, like Loafers, but have the tongue and toe of the Oxford model.

The classic laces have been replaced by one or two straps with buckles, which cross the surface of the shoe. The Monk model is very versatile and can be worn with both jeans and the most elegant suit.

Single Strap Monk Shoes

Single-buckle Monk shoes are more classic than double-buckle ones and don't draw as much attention. They preceded the double-buckle model and even though they aren't as popular as those, they will give you a nonconformist yet elegant look.

Double Strap Monk Shoes

For bold gentlemen who want to stand out in a positive and elegant way, the Double Monk model is the right choice.

This is much more popular than the buckle model, but just as versatile. Wear it with matching outfits with a casual suit or in a combination with a white shirt, chinos and a cardigan.

Loafers

Loafers are a type of men's shoe without laces. They are a slip-on style pair of shoes, which makes them extremely comfortable and easy to wear. Moreover, they save the wearer from the hassle of tying and untying the laces.

Men's casual shoes, loafers are not as elegant as lace-ups, but they can still be classified as men's dress shoes. Discover our entire collection of men's loafers .

Every piece has a story behind it, and loafers are no exception. When King George VI decided he wanted a shoe for the interior of his house, shoemakers created the first pair of loafers.

Designed to be worn indoors, this style of footwear quickly became an outdoor shoe that doesn't compromise on comfort.

The first thing to consider when choosing a pair of loafers is the type of leather you want the shoe to be made of. The most popular materials for this type of shoe are regular, cowhide, or suede, made from deerskin.

Loafers made from regular cowhide leather are much more durable than those made from suede, which makes them a pair of shoes worth investing in, because you will be able to enjoy them for a long time.

Suede models are a bit more demanding and require a lot more care. They are considered a pair of men's shoes for the summer, so wear them exclusively in the warm season to protect them from moisture.

In terms of style, suede loafers have a more casual look than regular leather ones, so they go best with casual, summery outfits.

Penny Loafers

Penny Loafers are the most classic loafer style. They lack any fancy details, such as tassels or other decorative applications.

If you are looking for a pair of shoes to go with jeans, then Penny Loafers are the right choice. They are extremely versatile, so you can wear them not only with jeans, but also with a pair of chinos or a casual suit.

Tassel Loafers

The “Tassel Loafers” are aptly named for their main feature - the tassel detail. They differ from the classic “Penny Loafers” model by the tassels placed on the band that crosses the surface of the shoe.

They were inspired by the design of boat shoes, which can be seen in the lace detail passed through large eyelets around the shoe, which ties inside, in the ankle area.

“Bit Loafers” shoes

Popularized by major fashion houses, the "Bit Loafers" model is characterized by a metallic detail located on the leather "strip" that crosses the surface of the shoe.

A pair of black Bit Loafers are elegant enough to wear with a suit, but not formal enough to pair with a black tie or white tie outfit.

What socks do you wear with men's shoes?

There are gentlemen who face a dilemma when it comes to what socks to wear with their shoes, especially formal ones. If you find yourself in such a predicament, know that there are some etiquette rules that you can follow.

In a formal or business environment, socks should be a must-have in your outfit. Moreover, they should be long enough to cover your ankle even when you're standing cross-legged.

Fashion advisors also recommend matching your socks to your pants, but not your shoes. Socks should be a visual extension of your pants, so it's not a good idea to choose a color that will clash.

If you want to have a relaxed look, you can choose to wear stockings with various patterns and textures. Opt for stockings in shades that harmonize with the rest of your outfit, for a pleasant chromatic look.

Never wear white socks with a pair of dress shoes. They only make the whole outfit look cheap and plain. The biggest style faux pas you can commit is wearing a pair of black pants with black shoes and white socks.

The situations where you can wear elegant shoes without socks are quite rare. Being a more casual type of footwear, the loafer shoe is the easiest to wear without socks on sunny summer days.

Even in these situations, Tudor Tailor fashion advisors recommend that you wear a pair of insole-type socks to avoid damaging your shoes.

How can you extend the life of your shoes?

A quality pair of shoes can be quite an investment, so you'll probably want to enjoy them for as long as possible. How do you store your shoes to extend their lifespan?

To ensure your shoes keep their shape when you're not wearing them, store them with wooden wedges inside and you'll be able to wear them for a long time to come.

Cedar shoehorns will not only keep your shoes in proper shape, but they will also absorb moisture and unpleasant odors. They are necessary for genuine leather shoes, which are more difficult to maintain than eco-leather ones.

Now that you know the types of men's shoes that should not be missing from your wardrobe and how to match them correctly, you will be able to coordinate your outfits so that they are worthy of a true gentleman.

If you want to see more men's shoe models, suitable for both elegant and business or casual outfits, visit our entire shoe collection and choose the model that suits your personal style.

If you want to have a unique fashion counseling experience, where you can learn more about the art of shoes or how to match men's formal shoes depending on the event, our fashion counselors are waiting for you in the Tudor Tailor showrooms in Bucharest, Cluj or Timișoara.