Dress shoes are a staple in a man’s wardrobe. No man is fully dressed until he has chosen the right pair of shoes. Whether you are wearing a suit every day and need a pair of dress shoes for daily use, or you are only dressing up on occasion and need that perfect shoe to really show off on your night out, you have to know which one is right for you. Of course, we’re not going to force you to go it alone while you search aimlessly through the world of men’s dress shoes. No way, we have done the hard work and found you the best of the best for any occasion and any type.
Oxfords
We don’t know if this was the first dress shoe. It probably wasn’t. Guys dressed up before Oxford students in the 1800s, right? Anyway, this is the most famous dress shoe, and for good reason. Originating on the campus of the namesake university, the Oxford is known by its closed lace system, meeting at the end of the laces in a ‘V’ shape. This keeps everything nice and tight, looking very put together.
Florsheim Sorrento Cap Toe
For your first dress shoe, you want it to be basic. Some may call it boring, but that is also a bit shortsighted. If you look at James Bond for inspiration, he doesn’t wear a lot of flash. He wears basic colors, basic patterns, with high quality and great fits. Florsheim offers all of those things, and you can wear these shoes every day with virtually everything. You may even get mistaken for a spy for MI6…or an Oxford grad…or both.
Derbys
The biggest difference between the Oxford and this shoe is the open laces on the vamp. While the Derby shoe has been seen as a more casual shoe due to the different feature, that has now been all but thrown aside as people start to look for comfort. The open laces provide a more free range of movement and are perfect for the guy with the higher instep or wider foot.
Johnston & Murphy Meade Plain Toe
Yeah, we love Johnston & Murphy. It is one of the places we always stop off when we have a little extra time to burn at the airport. Are we alone in that? Is everyone else running for the gate? Since the derby shoe is sometimes seen as a more casual shoe, wearing the black version adds a little more formality to this piece and will look amazing no matter what after the 6 pm event you pick them up for.
Brogues
Some people call them brogues. Some people call them wingtips. We call them essential. Originally, these shoes were designed for farmers to wear in wet environments. While the decorative patterns today are merely for show, they used to be actual holes that allowed water to drain from the shoe. Now, they are the picture of elegance.
Allen Edmonds McTavish Wingtip Oxford
Few brands are as storied and beloved in men’s shoes as Allen Edmonds. They are now and have always been at the top of the pile when put head to head with others. This tan wingtip or brogue is going to be your go-to for most occasions. It will look stellar with dark dress denim or any suit in your wardrobe (save for the black).
Monk Straps
It all started in the 1600s (or so we think) when monks swapped out their sandals for something a little more secure for manual labor. Gone were the open-toe thong sandals, and in were the closed-toe with a buckle. And like aristocracy does, they saw something they liked, and they took it for themselves, creating a men’s fashion where labor is nowhere to be seen. Now, the monkstrap is a sign of elegance and sophistication that we all need.
Thursday Boots Saint Double Monk Strap
Two straps are better than one (there is a song in there somewhere). While the monk strap may be a popular shoe that became huge in the dress world, the double monk doubled down on the look, literally. Thursday Boots currently has the best DMS on the market, and it will go perfectly with any of your double-breasted suits. If you want to wear these in a moment of casual rebellion, throw them on with denim and leave the back buckle on both shoes undone.
Chelsea
Since the mid-1900s, men’s shoes have seen many innovations and jumps in fashion trends. However, one shoe that rehashed an old-school look and revitalized it into an enduring staple in our shoe wardrobe is the Chelsea boot. While it was once a riding boot for royalty, the Swingin Sixties saw its adoption into men’s fashion by the likes of The Beatles and The Rolling Stones. Today, every closet needs a pair of these, and every playlist should have samples of both the above music staples.
Beckett Simonon Bolton Chelsea
Simple is the name of the game if you want a versatile pair of Chelsea boots. Sleek and sophisticated is the way to describe these made-to-order boots from one of the top games in the industry, Beckett and Simonon. The side gussets keep the boots easy to slip on without slipping once you’re wearing them. And the thinner ankle shaft keeps them nice and comfortable tucked under any pair of slim jeans or suit pants.
Boots
Boots are essential to any man’s wardrobe. They are perfect for protection, work, and casual moments. But, there is a special kind of boot that can take any outfit and elevate it to a place of elite sophistication. These are perfect with dark dress denim and a sportscoat. They are perfectly at home with chinos and a bomber jacket. With the right suit, they can make you stand out in a sea of boring people around you. Definitely need to find the perfect pair of dress boots in 2024. And, as you can imagine, we know just where to look.
TAFT Hamilton Boot in Blue Plaid
Sometimes, you just need to add some flare. Sure, you can throw on any old black, brown, or cordivan dress shoe with your outfit, or you can jazz it up with something truly unique. TAFT Boots completely changed the game with their one-of-a-kind looks and their ability to take something that shouldn’t work and prove us wrong by creating something stellar and the subject of envy. Even Elvis thinks you should have blue shoes, so pick these up and style your 2024 the right way.
Sneakers
We know what you’re thinking; this is about dress shoes. Not sneakers. Well, you should know by now that those two things can be one and the same. With the rapid casualization of our world (long before COVID but cemented by the quarantine), we saw the men’s fashion industry begin to adjust in a lot of ways. Flexible suit fabrics, moisture-wicking dress shirts, and dress shoes with soles of sneakers. Nowadays, especially if you have a job where you are on your feet all day, you need a pair of dress sneakers.
Cole Haan 2.ZeroGrand Laser Wingtips
When you think about the world of dress sneakers, few can be saddled with the credit for the trend more than Cole Haan. The ZeroGrand line of dress sneakers set the standard for smart casual and elevated business casual looks. When you need to look great and feel like you can go for hours on end without a chair, these are the shoes you have to pick up for your closet.
Loafers
With the new rise in “what is old is new again,” we are seeing all of our favorite styles of the past make triumphant returns. Things your grandfather and your father rocked are steaming back into the mainstream style. Pleated pants, smaller watches, and generally anything we can consider as grandpa core are all the rage this season. That means it is the perfect time to pick up a pair of penny loafers, which your grandfather loved so much. And you will, too.
GH Bass Weejuns Penny Loafer
If you are going to pick up a penny loafer, why would you ever do anything other than go with the original? These stellar examples of the style and unique class of the penny loafer could only come from the people who developed the very first in 1936, G.H. Bass. And, if you need some other convincing on why this shoe has stood the test of time, just remember that the legendary style icon himself from the White House, John. F. Kennedy rocked these regularly.
