July 26, 2022 / by Danny Mavis

Picture this – you’re at a formal event, and you’re feeling great. You’re wearing the ideal tuxedo, your hair is styled flawlessly, and you’ve got a great date on your arm. But then you look down at your shoes. Then you get to do some thinking – are your shoes really up to par? Are they going to ruin the entire look you’re going for?

If you’re not sure, don’t worry. You’re not alone. A lot of guys have a hard time picking out the right dress shoes and in certain instances they simply underestimate the importance of investing in quality footwear. Whatever the case may be, you can easily become a shoe-picking pro if you follow the basic tips and tricks below.

What Are the Different Types of Dress Shoes for Men?

First things first, you need to know that there are limits to the kind of footwear you can wear with formal clothing. Most of them have the same general shape, but there are some subtle differences that make a big difference in the overall look.

Dress Boots

picture of men walking in stilish outfit and a pair of stylish mens leather dress boots
source: Brooke Cagle on Unsplash

Kicking off the list is a pair of stylish mens leather dress boots perfect for guys who want to add a touch of sophistication to their look without going overboard. They’re dressy enough to match a suit but not too formal that they can’t be worn with more casual clothing, like jeans.

Generally speaking, there are two major types of dress men’s boots: chukka and chelsea boots. The former is characterised by its open lacing system and ankle-high design, which are both features that make it perfect for more casual ensembles.

Meanwhile, the latter option of stylish mens leather dress boots is a more formal style of boot, and its main distinguishing feature is its elasticated side panels, which make it easy to slip on and off. This particular design means there’s no need for laces, making it a great option for guys who want something that’s both stylish and easy to wear.

Either way, both types of mens dress boots are great choices for guys who want to look dapper without being too over-the-top. The key is to find a pair that fits well and is comfortable to wear so you don’t have to worry about getting blisters or sore feet halfway through the night.

Just make sure your pants are the right length – you don’t want them to be too long and cover up your boots, nor do you want them to be too short and expose too much of your ankles. The perfect pant length should sit right on top of your shoes, so keep that in mind when you’re getting dressed.

Oxford Shoes

picture of men sitting on a sofa putting on his leather Oxford shoes
source: Rosie Sun on Unsplash

Next on the list are oxford shoes, and these are probably the most formal type of dress shoe a man can own. They’re often seen worn by grooms at weddings or by waiters at high-end restaurants, but that doesn’t mean you can’t rock a pair yourself.

The most noticeable difference between oxford shoes and other types of formal footwear is the lacing system. Rather than having the laces attached to the side of the shoe, they’re sewn underneath the vamp – and this gives the shoes a much sleeker and more polished look.

Another thing that sets oxford shoes apart is their design. Unlike other types of dress shoes that are made up of multiple pieces of leather stitched together, oxfords are usually made from a single piece of leather that’s been shaped to fit the foot. This construction gives the shoes a sleek and streamlined look.

Derby Shoes

picture of men walking wearing winter coat, and a pair of stylish mens leather dress boots
source: Valiant Made on Unsplash

Derby shoes may be considered the more casual cousin of oxford shoes, but don’t let that fool you – they can still be worn at both formal and semi-formal events. The lacing system is, yet again, the most apparent trademark of this type of shoe.

Unlike oxfords, the lacing system on derby shoes is attached to the side of the shoe, which gives it a more relaxed and laid-back look. Each side of the shoe also usually has a different leather panel, which gives it a bit more texture and interest.

Brogue Shoes

picture of clothes layed on the bed beside a box with a pair of stylish mens  leather dress boots
source: David Lezcano on Unsplash

While they may seem similar at first glance, brogue shoes are actually able to hold their own as a distinct type of dress shoe. By far the most exciting feature of this shoe is the perforated pattern on its surface – which is what gives it its name.

The holes, or ‘brogues’, were originally functional, as they allowed water to drain from the shoes when walking through wet terrain. Nowadays, though, they’re purely aesthetic and are there to add visual interest to the shoe.

Brogue shoes come in both lace-up and slip-on varieties, so you can choose the style that best suits your needs. They also come in a variety of different materials, from leather to suede, so you can really mix things up and experiment with different looks.


picture of a brown loafers and blue polo shirt on a white plastic chair
source: Jeroen den Otter on Unsplash

Loafers are the perfect type of shoe for guys who want something that’s both stylish and comfortable. They’re slip-on shoes, so they’re easy to manoeuvre on and off your feet and they often have tassels or other decorations on the front.

They’re normally made from soft materials like suede or leather, which makes them breathable and comfortable to wear even if you’re on your feet all day. While they’re generally considered to be casual shoes, they can still be dressed up with the right outfit.

Monk Strap Shoes

picture of a men standing wearing brown leather monk strap shoes
source: Phillip Wood on Pinterest

Last but not least are monk strap shoes which are a bit more unique than the other types of dress shoes on this list. Rather than laces or a slip-on design, they have a strap that fastens across the top of the foot – hence the name.

Despite their unusual design, monk strap shoes are actually very versatile. They can be paired with different styles, depending on the occasion, and they come in both single- and double-strap varieties.