Wearing the right shoes can elevate any outfit from boring to sophisticated fashion. Elegant shoes enhance every outfit, whether casual or formal. The best dress shoes for men are not only stylish, but also practical.
Everyone wants to look their best and in their best shoes, but not everyone knows how. You don’t want to have a fashion faux pas in the middle of a formal event. Worse, you don’t want to spend a fortune to wear the most expensive clothing brand’s shoe, only for it to go out of style in a few months.
Different styles of shoes suit different occasions and outfits. Some shoes should only be worn on formal occasions and others should never be worn with an evening dress. Thankfully, this guide will help you avoid fashion mishaps in the future.
Take a look at eight timeless styles of dress shoes that every man should have in his closet. They give every outfit a classy look.
The 8 best evening shoes for men
Dress shoes should remain timeless and go with almost any style of clothing you wear. Whether that style is formal, casual or anything in between. Black or brown dress shoes with a smooth leather or suede finish are always a safe bet.
1. Oxford shoe
Oxford shoes are a good place to start when shopping for a dress shoe. It’s a basic shoe that’s versatile enough to wear almost anywhere. Depending on their color and style, they can dress more elegantly or more casually.
The shoe grew in popularity among Oxford University students in the 19th century. The aim was to show the status at that time.
The most recognizable features of an Oxford shoe are the closed lacing, the low heel and the long toe. It comes in four different styles, but the most common style is the Cap Toe Oxford. This type of footwear is most commonly 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 special characteristics. Unlike oxfords, derby shoes have an open lacing system.
This means that the vamp (section on top of shoe that covers foot) is split in half and laced up.
The wider, more comfortable lacing makes this shoe more casual. The smooth leather designs give every outfit a classy look. A plain derby is the most versatile option as it can be a formal or casual dress shoe.
3. Zero drop dress shoe
Oak With their foldable slip-on design, dress shoes are the perfect travel companion for any trip. Unlike traditional dress shoes, Oaka’s zero-drop profile offers superior comfort while still giving you a sleek look that won’t go unnoticed.
The faux heel at the back adds elegance and keeps your foot flat on the ground. Plus, after a long day of meetings or sightseeing, you don’t have to worry about removing dirt from your shoes – they’re machine washable.
Whether you are going on an important business trip or just enjoying your vacation, this Zero drop dress shoe offers all-day comfort without compromising on style. Lightweight yet durable, these modern dress shoes have an upper made from Flyknit fibers that help reduce production waste.
Oaka Zero Drop Dress Shoes are available in Ash Gray and Ink Black. We tried them personally and found them as comfortable as sneakers!
4. Chelsea boots
These laceless boots are minimalist and timeless. They originated in the 19th century and gained popularity at Chelsea in London, from where they got their name. They’ve been a staple in men’s capsule wardrobes ever since.
Chelsea boots are traditionally made from leather but can also be found in suede. The silhouette of the boot is the strongest pull point.
The Chelsea boot is designed to be snug and cut right at the ankle to avoid bulk. The elastic side panel on the shoe provides a comfortable fit so you can wear it all day.
5. Low shoes
The origins of the loafer are a bit hazy as there have been different variations of the shoe in many cultures throughout history. Native Americans wore a shoe similar to moccasins. Fishermen in Northern Europe also had a variation of the shoe.
Loafers are versatile slip-on shoes with nine different shoe styles. Penny loafers are the most versatile of the nine categories.
The other types of loafers are horsebit, kiltie, driving, slipper, boat shoe, bit loafer and espadrille. Invented by Aldo Gucci in the 1960s, bit loafers have a piece of metal over the vamp.
Tassel loafers are a popular choice for business attire or weddings. The elegant shoe goes well with long pants, trousers or shorts for a smart casual look. However, evening wear and loafers do not go together stylistically.
6. Dress boots
Dress boots are slim and have an elegant look that resembles an oxford or derby shoe. They have been in fashion since the Victorian era and are still worn by many today. They are great for the cold winter months due to their high ankles.
Dress boots are more casual shoes and should not be worn with suits or tuxedos. These boots go well with casual wear like jeans or pants. They instantly add some sophistication to an otherwise boring outfit.
7. Monk Strap
Monk straps were developed by European monks in the 15th century. They wore this type of shoes while working in the fields. Modern monk straps have single, double or triple buckled straps at the top.
A shoe with a strap is the most formal of all due to the lack of details that create a slimmer look. This comfortable slip-on shoe is more formal than a loafer. Just use a little bit of it Cleaning shoesand you can wear monk strap shoes to formal occasions.
8. Chukka boots
Chukka boots were originally worn as casual wear in the United Kingdom in the 1940s. Today the tradition lives on and the boots can still be seen in both formal and casual attire. It’s the open toe and ankle length design that allow 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 works best with formal wear because of the simplicity of the style.
A chunky sole makes the shoe more casual and relaxed. These popular men’s boots look great in both leather and suede.
9. Opera pumps
Opera pumps are 19th-century formal slippers worn only with evening wear. They are usually black and adorned with a bow at the top. The shoe is typically made of quilted silk or black patent leather with a high-shine finish.
Although not as popular today as they were in the Victorian era, these elegant shoes are sure to elevate any formal attire. They are standard shoes that can be worn with a white tie, but they can also be worn to black tie events.
Final thoughts on men’s shoes
You may have heard of brogue shoes. Somewhat confusingly, brogues are not actually a type of men’s shoe, but rather a decorative element.
First worn by Irish and Scottish workers in the 18th century, brogues have perforated holes which are believed to have originally allowed water to drain when the wearer walked on swampy ground.
There are different types of men’s brogue dress shoes:
- Full brogue – also known as wingtips, these very decorative shoes have a pointed toe cap with W-shaped extensions.
- Half brogue – invented by the John Lobb company, Half Brogues feature a perforated medallion pattern on the front of the shoe.
- quarter brogue – these shoes have a minimally perforated detail on the seam of the toe.
Dress shoes are a timeless staple that every man should have on his shoe rack. With the right shoe, shirt collar, pocket square and a luxurious watch, you’ll 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 on special occasions. The more you know about dress shoes, the better your style can be.
Whether you prefer a sleek toe or a more decorative style, these eight classic dress shoes will keep any man comfortable no matter what he’s wearing.
Interested in luxurious men’s style? Check out these other luxe style features:
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