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Shoes Every Man of Style Should Have in His Wardrobe

Updated: Oct 18, 2023

A good pair of shoes is one of the most important things a man can own. They set the tone for your entire look and having a well-crafted shoe that perfectly fits your foot is more comfortable than you can imagine.

There are certainly many different types to choose from, so we thought it would be helpful to point out our five favorite styles every guy needs in his wardrobe:

1. The Brown Brogue

The staple of the traditional Englishman since the 19th century, this shoe has a sleek shape and refined finish. It is ideal for pairing with business-casual attire or even a classic, dark suit. The Brogue, or type of wing tip design shoe, was originally created to improve traction on wet roads, and it still serves as a unique accessory today.

Brogues are traditionally part of a man's formal dress wear, but they have become an increasingly popular casual choice in recent years. If you're looking for your first pair, start with either a semi-brogue or quarter-brogue. For those who like to keep up appearances, we suggest getting full brogues (wingtips) which will turn heads when paired with jeans and chinos alike.

Final analysis:

The brown brogue has been a staple of men's footwear for nearly two centuries. It can dress up your jeans or bring a touch of class to an otherwise formal suit, making it perfect from dawn till dusk and in any situation—from work to dancing.

2. The Suede Chukka

This is a perfect shoe for spring and summer. The chukka features a leather or suede upper paired with leather laces and eyelets, which gives it an interesting contrast of textures. It's also a versatile shoe that can be worn with everything from jeans to shorts.

The chukka provides the perfect balance between formality and casual wear. It's dressier than your average sneaker but not as formal as an oxford. The chukka can be worn with anything from jeans to suits, depending on how you want to look for any occasion.

Final analysis:

Chukka boots are the perfect solution if you're unsure whether your outfit is too dressy or too casual. They make anything from a suit to an off-duty ensemble look effortlessly cool and fashion-forward without making it seem like you were trying, which makes them ideal for all sorts of occasions.

3. The Brown Loafer

This is our most versatile shoe since it pairs well with just about anything. The classic loafer features an accent on the heel, generally made of a contrasting material such as suede or leather. You can find many different loafer variations, but all are excellent choices for casual wear.

Though it may not be the best shoe for a formal suit, loafers are an easy way to spruce up any outfit. This classic men's style can go great with jeans or chinos and paired with your favorite sport coat. A suede loafer is perfect if you're looking for something dressier, while a leather one will give off that casual vibe.

Final analysis:

Loafers are the perfect shoe for the summertime. They're easy to slip on and super stylish, making them a staple of your weekend rotation.

4. The Minimalist Sneaker

This shoe is best for dressing down your look. The sleeker and simpler the sneaker, the more versatile it will be in your closet. A nice pair of sneakers is a must-have for summer: they carry you from running errands to taking a casual stroll with friends without looking out of place no matter where you go.

Sneakers are versatile, comfortable, and go with everything. There is nothing better than a laid-back pair of canvas sneakers when you're not at work or out partying. Stylish and comfortable, it's perfect for any occasion, from ball games to backyard barbecues. Minimalist sneakers in a brown, beige, white or gray color are simple and chic. These will never go out of style because they are so easy to wear with any outfit.

Final analysis:

The canvas sneaker is the epitome of what a summer shoe should be. It's hands-down better than your average flip flop because it can be worn with just about any casual outfit and look great while still providing comfort for long days at work or play.

5. The Oxford or Derby

This is the ultimate dress boot. The Oxford (also known as a "blucher" in some circles) has become more popular over the years and can make any suit look sharper. The Derby (a close cousin to the Oxford) has been worn by men since at least the 1600s when it was originally used for horseback riding, hence its name. Today, it's a staple of formal wear.

A pair of black Oxfords or Derbys is the first formal shoe a man typically owns. But the square-toed variety should be avoided, as it lacks refinement compared to more classic rounded toe Oxford's and Derbys, which are much better suited for any occasion.

If you're wondering where the difference between Oxfords and Derbys lies, it’s the lacing. First, Oxford shoes have closed laces, while Derby shoes are open-laced. Secondly, Oxfords are a much more formal footwear choice for business or dress occasions.

Final analysis:

Go with a classic black or brown here, and you won't be disappointed. Black is appropriate for formal occasions like funerals, weddings, and black-tie events; Brown can be worn in more casual settings, with lighter shades being more relaxed. A nice cap-toe Oxford or Derby is our recommendation if you want to start off right.

6. The Brown Leather Boot

Boots are the perfect way to add an extra touch of style or rebellious ruggedness to your look. Depending on what you're looking for, there are boots for every occasion. First, there are dressy varieties like chelsea boots that can be worn with a suit, and casual work boots that make any outfit more cool. And if those don't tickle your fancy, how about some chukkas? They'll class up just about anything in seconds while staying comfy all day long.

There are plenty of options when it comes to boots for work or play. Whether you're looking for a more casual boot, stylish dress boots, or just something functional and durable enough to withstand daily wear is up to you. But remember, well-worn looks good on everyone, so don't be afraid of those scuffs and seams. Embrace them instead with confidence, knowing they'll only enhance the look even further over time, as well as give off an air of rugged style not many other shoes could achieve.

Final Thoughts

The shoes make the man, and a gentleman must be prepared for any occasion. These classic choices we discussed will carry you through life's big moments, all while always looking refined and stylish.

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