Wearing the right shoes can take any outfit from boring to sophisticated fashion. Dress shoes elevate any outfit, whether it’s casual or formal wear. The best dress shoes for men are not only stylish but practical as well.
Everyone wants to put their best foot forward and in their best shoes, but not everyone knows how. You wouldn’t want to have a fashion faux-pas in the middle of a formal event. Worse yet, you wouldn’t want to spend a fortune wearing the most expensive clothing brand’s shoe only for it to go out of fashion in a few months.
Different shoe styles suit different occasions and outfits. Some men’s dress shoes are only to be worn to formal events, and others should never be worn at a black-tie event. Thankfully, this guide will help you prevent any fashion mishaps in the future.
Take a look at eight timeless types of dress shoes that every man should have in their closet. These formal shoes for men give a classy look to any outfit.
10 Best Dress Shoes for Men
Men’s dress shoes should remain ageless and work with almost any style of clothing you wear – whether that style is formal, casual, or anything in between. Brown or black dress shoes with a sleek leather or suede finish are always a safe bet. The main thing is to pick comfortable dress shoes.
1. Oxford Shoe
Oxford shoes are a good starting point when you’re buying a dress shoe. It is a basic shoe that is so versatile that it can be worn almost anywhere. Depending on the color and style, they can be dressed up or down.
The shoe gained popularity in the 1800s among Oxford University students. The aim was to exhibit your status at the time.
The most recognizable characteristics of Oxford dress shoes are the closed lacing, low heel, and long toe. It comes in four different styles, but the most common style is the Cap Toe Oxford. This style of shoe is most often worn as business attire or for formal occasions.
2. Derby Shoes
Derby shoes are often confused with Oxford shoes. They are quite different once you know their distinct characteristics. Derby shoes, unlike Oxfords, have an open lacing system.
This means that the vamp (section on top of the shoe that covers the foot) splits in half and laces.
The wider, more comfortable lacing makes this shoe more casual. The smooth leather designs give any outfit a polished look. A plain derby is the most versatile option as it can be a formal or casual dress shoe.
3. Zero Drop Dress Shoe
Oaka dress shoes are the perfect travel companion for any journey, with their foldable, slip-on design. Unlike traditional dress shoes, Oaka’s zero drop profile offers superior comfort while still giving you a smart look that won’t go unnoticed.
The faux heel in the back adds elegance and enables your foot to stay flat to the ground. Plus, after a long day of meetings or sightseeing, you don’t have to worry about removing dirt from your shoes – they are machine washable.
Whether you’re headed for an important business trip or simply enjoying your vacation, this zero drop dress shoe provides all day comfort without compromising style. Light weight yet durable, these modern dress shoes have an upper made from flyknit fibers that help to reduce production waste.
Oaka Zero Drop Dress Shoes are available in Ash Gray and Ink Black. We’ve tried them personally and found them to be as comfortable as sneakers!
4. Chelsea Boots
These laceless boots are minimal and timeless. They originated in the 19th century and gained popularity in Chelsea in London, which is where they got their name. They have been a classic staple of men’s capsules wardrobes ever since.
Chelsea boots are traditionally made of leather but can be found in suede as well. The silhouette of the boot is the strongest pulling point.
The Chelsea boot is tight-fitting and cut right at the ankle to avoid adding any bulk. The elastic side panel on the shoe gives them a comfortable fit so that you can spend all day in them.
5. Loafers
The origins of the Loafer are a bit fuzzy because there were different variations of the shoe worn throughout many cultures in history. Native Americans wore a similar shoe to the loafer called moccasins. Fishermen in Northern Europe also had a variation of the shoe.
Loafers are versatile slip-on dress shoes. The penny loafer is a classic style of slip-on shoe that features a leather strap across the instep, typically with a diamond-shaped cutout or slit at the center.
The name “penny loafer” is derived from the practice of inserting a penny into the slit as a decorative embellishment, although this is very rarely done today. These shoes are known for their flexible and timeless design, making them suitable for both casual and semi-formal occasions.
The other types of men’s loafers are horsebit, kiltie, driving, slipper, boat shoes, bit loafer and espadrilles. Bit loafers were invented by Aldo Gucci in the 1960s and feature a piece of metal across the vamp.
Tassel loafers are a popular choice for business attire or weddings. The dapper shoe matches well with long pants, slacks, or shorts for a smart casual look. However, black tie and loafers do not mix style-wise.
We particularly like the water-repellent, Italian suede loafers by Amberjack. Designed in Brooklyn, New York, they’re made by skilled artisans in Portugal and feature a sheepskin lining, dual function athletic outsole and heat activated arch support. What’s more, they offer free shipping, free returns and a 2 year warranty.
Amberjack also make a range of other comfy yet stylish dress shoes such as Cap-Toe, Slip-On and The Tux shoes.
6. Dress Boot
Dress Boots are slim and have a dressy look that is similar to an Oxford or Derby shoe. They have been in style since the Victorian era and are still a fashionable option worn by many today. They are great shoes to wear during the cold winter months because of their high ankles.
Dress Boots are more on the casual side of footwear and are not recommended to wear with suits or tuxedos. These boots pair well with casual wear like jeans or slacks. They instantly add some sophistication to an otherwise bland outfit and are great for the weekend.
7. Monk Straps
Monk Straps originated in the 15th century by European monks. They wore this style of shoe while working the fields. Modern-day Monk Straps have single, double, or triple buckled straps across the top of them.
A single strap shoe is the most formal out of the bunch because of the lack of detail which creates a sleeker look. This easy slip-on shoe is more formal than a loafer. Just use a bit of this shoe shine, and you can wear monk strap shoes to formal events.
8. Chukka Boots
Chukka Boots were originally worn as casual wear in the United Kingdom during the 1940s. Today, the tradition lives on and the boots are still seen in both formal and casual attire. It is the open lace and ankle-length design that allows this comfortable shoe to be more versatile in style.
A Chukka Boot can be a formal or casual shoe depending on the silhouette you choose. A slim silhouette is best for formal wear because of the simplicity of the style.
A chunky sole will make the shoe more casual and laid-back. These popular men’s boots look good in both leather and suede.
9. Wingtip
Wingtip dress shoes, also known as brogues, are a classic and stylish footwear option suitable for formal or business attire. These shoes are characterized by decorative perforations and a wing-shaped cap on the toe, lending them a distinctive and elegant appearance.
The perforations, or broguing, can vary in complexity, ranging from subtle to more elaborate designs. Wingtip dress shoes are often crafted from high-quality leather and are available in various colors, making them a versatile choice for complementing a range of outfits.
With their timeless appeal and sophisticated detailing, wingtip dress shoes are a popular choice for individuals seeking a refined and polished look for semi-formal occasions or professional settings. However, they’re not usually worn for the most formal events such as funerals.
10. Opera Pumps
Opera Pumps are formal slippers from the 19th century only worn with evening wear. They are typically black in color and adorned with a bow on the top. The shoe is typically made with quilted silk or black patent leather with a high gloss finish.
Although not as popular today as in the Victorian era, these men’s dress shoes will certainly elevate any formal wear. They are standard shoes to wear with white tie attire but are acceptable to wear to black-tie events as well.
Final Thoughts on Men’s Dress Shoes
You may have also heard of brogue shoes. Somewhat confusingly, brogues aren’t actually a type of men’s dress shoe, but a decorative feature.
First worn by Irish and Scottish workers in the 1800s, brogues have perforated holes which were thought to originally enable water to drain out when the wearer walked on boggy ground.
There are several types of brogue dress shoes for men:
- Full Brogue – also known as wingtips, these highly decorative shoes feature a pointed toe cap with extensions in a W shape.
- Half Brogue – invented by the John Lobb company, half brogues have a perforated medallion pattern at the front of the shoe.
- Quarter Brogue – these shoes have a minimal perforated detail on the seam of the cap.
Dress shoes are an ageless staple every man should have on their shoe rack. The right shoe, shirt collar, pocket square and a luxurious watch can make you look effortlessly stylish.
Most dress shoes can be either formal or casual, like an Oxford Shoe. Others, like an Opera Pump, can only be worn to special events. The more you know about dress shoes, the better your style can be.
Whether you prefer a plain toe or a more decorative style, these eight classic dress shoes will have any man feeling their best no matter what they wear.
