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The Top 6 Shoes That Every Guy Should Own | The Dress Shoe Guide For Men

How does the old saying go?

“The shoes make the man” ? Or was it the football team he rooted for?

I can’t remember. But here is a fact;  SHOES are the number one thing that ladies notice when sizing you up.  

That’s right, while you’re spitting your “game” at them, they are taking notice of you too. That is why you need to make sure that your “first impression” game is just as strong as your one liners.

But fear not! I have compiled a list of the top 6 shoes that should be in every guy’s wardrobe.   This is not an exhaustive list. You can definitely have more (cc: sneaker heads), but I believe that these are your staple pieces to get started.

The Oxford

“Oxfords, not Brogues” – The Kingsman….anyone?

This line of the movie made me chuckle a little bit because technically you can have both brogues and an oxford design simultaneously. It’s comparing apples to oranges. (See definition of brogues below)

The textbook definition of an oxford is a shoe that has the closed lacing system, that is when the eyelets are sewn in underneath the vamp of the shoe. The opposite is found on a derby (blucher)  which has open lacing.

Both oxfords and derbies can have brogues on them, but the formal oxford will have none. Brogue perforations are considered less formal.

Usually, oxfords are solid black or brown with a cap toe. This shoe is classic, timeless, and should be worn when wearing your professional attire.  This is my personal go-to shoe when I suit up.

BroguesThe Wingtip Brogue

To go into a little further description of the definition of a brogue, it is simply the decorative perforations found on the shoe.

The wingtip is the W shape on the end of the toe.

As you can see in this example it is both an oxford AND a brogue.

For simplicity sake, let’s just say that a brogue has the cool little holes in them and are a little more casual.

These are usually worn with chinos, denim, or business casual attire. You can find brogue patterns on most dress shoes, as this decorative piece blends well with several shoes categories. Make sure you have at least one type of brogue in your closet.

The Monk Strap

Going back many centuries, monks used to wear these when they worked.

They were more durable than the sandal and easy to slip in and out of. Of course, like all historical timeless pieces, we have taken traditional uses for things and turned them into stylish innovations.

Monk straps come in single or double straps and are usually a little less formal than the oxford. The lack of laces makes this shoe an eye catcher from the get-go.  It can technically fall into the loafer category since it has buckles instead of laces, but they have earned a right for a separate category.

I would place the monk strap in the middle on the formality meter. However, I have definitely rocked double monk straps with a suit before, but I mean what can I say, I like to live life dangerously.

The Chelsea Boot

The King of boots.

Created by Queen Victoria’s shoemaker, and made famous by The Beatles, the Chelsea boot can go with almost every style.

They are the epitome of versatility.

You can wear them with denim, chinos, and even suits. The Chelsea boot is a must have every guy’s wardrobe.

The best place to wear Chelsea boots is during travel. The ease of slipping in and out of them at the airport combined with their stylish appeal makes them my go to shoe for travel.

The fact that they upgrade your casual style is also a plus. Next time you wear a t-shirt and jeans, swap your sneakers for a pair of Chelsea boots and you will see an instant elevated casual look.

The Trainers

One of the best ways to be in style is simply staying fit.


Trainers are important for your fitness but also happen to be pretty stylish as well. They go with every casual outfit.

If possible, have a couple different pairs of trainers because you don’t want one building up too much odor from workouts and everyday wear. If you’re on a budget, one pair is just fine.

The Penny Loafer

Of Norwegian descent, the loafer comes in several different styles.

This particular shoe deserves an entire post in itself to learn the history and styles so we will just keep it to how to wear it.

This shoe is in the slip-on family and it hovers between casual and professional. It falls underneath black and white tie affair formality, but can definitely be worn in a business professional and business casual setting.

The most important thing about the loafer is its convenience. It is easy to get in and out of. I like to wear a loafer when traveling to get through airport security quicker.

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