Casual sneakers seem to be the most popular type of footwear, don’t they? That makes it really easy to forget the sheer variety of different types of dress shoes available.

Let’s not forget those certain occasions where dress shoes are almost mandatory. Yes, a pair of clean white low-top sneakers can look really cool with a formal suit. But iconic types of dress shoes like Chelsea boots will never go out of fashion and will elevate your outfit to a whole new level.

And dress shoes need not always be styled with a suit either. A nice pair of suede loafers can really add a luxury vibe to a cool pair of jeans for a more casual look. There are several well-established styles of dress shoes every guy should know about, from Oxfords to wingtips and everything in between.

Let’s learn about them together, shall we?

Key Takeaways

This is one area of the fashion world where fine craftsmanship and quality of materials reign supreme. Take Loake, for example, offering a stunning wingtip. And it’s hard to miss with a pair of classic brogues from Church’s.

Then you have newer companies such as Oliver Cabell coming in hot with luxury loafers. If you’re looking for a timeless yet nostalgic option, turn to Dr. Martens Oxford. It’s never a bad idea to start a collection of dress shoes, but as long you have one or two staples, you’re setting yourself up for success.

While more on the casual side of dress shoes for men, Chukka boots deserve their place on the list of different types of dress shoes for men. Often crafted from rough suede, these Chukka boots by Morjas strike a dressier note in smooth waxed suede.

Chukkas essentially fill the gap between traditional shoes and high boots, perfect for smart casual outfits. Being constructed from waxed leather, these particular boots are also waterproof.

Perfect for weekend strolls or chilling out at the weekend. They look really comfortable too.

How clean do these sand suede blucher shoes by Morjas look? With a handmade construction boasting no less than 128 individual steps, the beautifully crafted premium suede is a nice addition.

They’re also available in eight different colors, so you’re sure to find a pair that perfectly fits the bill. The brown sole of these shoes contrasts beautifully with the sand-colored upper. And being suede, the shoes can be dressed up or down. Store these with a shoe tree inside after use to maintain their shape and iron out any creases from wear.

Who said dress shoes have to be black or brown polished leather? Suede, particularly in a light color such as these ‘cement’ gray loafers by Oliver Cabell, is equally dressy. And these loafers look incredibly comfortable with such a soft aesthetic and an Italian calfskin lining.

Hand-stitched and available in a wide range of colors, these will look great with a smart casual outfit. Strictly for dry days, though. That suede looks super vulnerable to damage, but keep these shoes well, and they will last for years.

Sometimes you need a dress shoe for a particular purpose, and opera pumps are a case in point. Is there a more formal occasion than a night at the opera?

Opera pumps are often crafted from leather, but always one to stand out, I have chosen these elegant suede shoes by Velasca instead. Black suede couldn’t be more dressy if it tried, and with a black bow design at the front, you may just show up King Louis XIV if he turns up on the same night.

Definitely a shoe you will have for years. Given its specific occasional use, it makes sense to invest in a high-quality pair of opera pumps such as these handmade Italian shoes.

Boots are a great choice of dress shoes for men looking to add some attitude to their outfit, and Swedish brand Myrqvist offers some really unique choices. The Abisko boot is a great alternative to Cheleas.

Plus, they’re super dressy thanks to the calf leather exterior paired with simple stitching construction. They also feature a stacked leather heel and a highly elegant upper with a almond toe. They’re hand-crafted in Portugal, and the pull tab at the rear is really handy when slipping these on.

Pair these with jeans for a casual luxury vibe, and you can’t go wrong.

Personally, Chelsea boots are my favorite of all types of dress shoes for men. Elegant, classic, and easy to slip on, thanks to their expandable side gore.

Check out the elongated silhouette, classic chiseled toe, and artisanal sole swept up into the upper via super-fine hand-stitching. Now examine the cognac leather upper. You can almost see each grain in the highly polished and deep luster of the finishing. This is artisanal craftsmanship on an entirely new level.

Let’s start with a completely left-field but still trendy choice. The Dr. Martens 1461 is a really cool option if you want to add some personality and style to your outfit, even if that outfit is a format suit.

The Dr. Martens 1461 can be dressed up or down, with a fresh pair looking super smart yet edgy at the same time. While available with the traditional low Dr. Martens sole, the ‘BEX’ model I have chosen with a thicker sole will lend any outfit a more elevated edge. Plus, I think it’s also a slightly more unique choice.

It goes without saying that Docs look amazing in their natural casual habitat too, but they can also play the dress shoe game equally well.

Derbies are one of the most classic silhouettes of all time. While there are thousands of options out there, these aptly named ‘Timeless’ Derby shoes by Christian Dior are particularly unique.

With the famous Dior ‘Oblique’ print subtly applied in gradient form to these highly polished calfskin leather shoes, the effect is uber elegant and luxurious.

Derby shoes like these feature neat open lacing, and the overall silhouette is perfect for any formal occasion where a suit is required. Christian Dior shoes and accessories always take an outfit to the next level. Given the cachet of the brand, I would recommend pairing these shoes with a minimal black suit for maximum effect.

I challenge anybody to find a pair of monk straps as elegant, creative, and beautifully made as these Islaro II shoes by Magnanni. They almost belong in a museum of modern art. And not only is the slimline silhouette incredibly elegant, but the shoes feature a double monk strap.

The hand-craftsmanship is sublime, while the beautiful leather is hand painted such that no two pairs are identical. The Islaro II is also super comfortable, thanks to Magnanni’s Artesano sole. The secret is that it wraps into the side of the shoe for an artisanal hand-stitched touch.

A shoe that still appears elegant and minimal in its overall appearance. You just can’t go wrong here.

With a Royal Warrant and seal of approval, Loake Shoemakers need absolutely no introduction. As a shoemaker for over 140 years, Loake knows a thing or two about the craft, even supplying shoes to the British Royal Family over the past century or so.

The Loake Buckingham is a perfect example of the classic wingtip, so named for the wing pattern of the stitching at the tip of each shoe. Handmade in Kettering, England, using premium calfskin leather, they’re perfect for pairing with any formal black or gray suit.

Another one of the oldest British shoemakers in the game is Church, with a heritage that dates back to 1617.

Skilled in the art of fine craftsmanship, their brogue shoes are appropriately named the ‘Dickens.’ Charlie boy probably even owned a pair, as Church would have celebrated its 200th anniversary during the great writer’s lifetime.

I particularly like the minimal vibe, with their perforated decoration to the upper and slimline silhouette. The attention to detail is superb with leather piping, vintage ‘Church’ embellishments to the inner sock and sole, and a natural finish Doha leather.

Purchasing a pair of these brogue shoes is almost like buying a piece of history.

The stately name of these whole-cut shoes almost tells you all you need to know about their heritage and quality. They quite literally meet the gold rating, which they were awarded by the Leather Working Group.

Whole-cut shoes are the most minimal interpretation of classic types of men’s dress shoes with maximum class. The upper is seemingly cut from a single piece of leather with no seams for a smooth result.

These Valencia’s are a nice alternative to the more traditional types of dress shoes for men. Pair these with a navy suit for an elegant and supremely classy outfit, perfect for a wedding.

Final Verdict

It’s always good to have perhaps two types of dress shoes in your closet. one for super formal occasions where a suit is mandatory, and another if you wish to elevate a more casual outfit. For example, high-quality boots with a smart-casual office look.

It is possible to buy a pair of dress shoes at almost any price point, so don’t feel pressured to spend your life savings. but if you want something of super quality that won’t go out of fashion, it makes sense to invest a little more.

A level of hand-made craftsmanship and fine detailing will make wearing your dress shoes an occasion each time you take them out of the box. Choose wisely.