The Essentials List Part 3.1: Dressy Footwear

The Essentials List Part 3.1: Dressy Footwear

Footwear can be very tricky to buy since shoes have a more functional purpose than any other item in your wardrobe.  Every day your shoes take a beating from the weather, sidewalks, dirt and your own body weight. Finding a well-made shoe with the right fabric composition can really make a difference in terms of durability, longevity, comfort, and ultimately, the lifespan of your shoes. Living in a four season country like I do, it’s important to remember these details because it could be the difference between being inappropriately dressed and getting sick or staying warm and outlasting the elements.

Apart from the importance of functionality, your footwear choice can make or break an outfit, so choose wisely. Keep in mind that most footwear doesn’t follow the same strict rules and guidelines that apply to other aspects of menswear. A shoe can have textured leather, contrasting colours, studs, and even abstract prints but remember the most timeless styles will give you the most versatility!

Below I have put together a list that will give you a better idea of what styles to go for, what to spend on each, and what to compromise on. It’s time to take a good hard look at your shoe game!

 Black dress shoes

black dress shoes
1. Cap toed lace up     2. Double monk strap     3. Wingtip Lace up

I know you’re thinking you already have a pair of good black dress shoes, but before you get ahead of yourself, ask yourself a few questions: are they square toed or long and pointed? Are they faux leather?  Are they uncomfortable? Are they beyond repair? If you answered yes to one or more of these questions it may be time to update your black dress shoe!

Black dress shoes should be a staple in every man’s wardrobe. Even if your job doesn’t call for formal attire there’s bound to be an occasion when you need a good black dress shoe and having a more versatile pair will go farther in the long run.

There are probably thousands of black dress shoes to choose from but above I have chosen three that are not only modern and fashion forward, but also classic enough for you to be able to wear them again and again. When it comes to price don’t be afraid to spend a little extra here. Consider them to be a wardrobe essential, a staple you’ll be able to reach for time and time again. And remember, you should always invest money in those pieces as they make up the anchors of your closet!

Brown dress shoes

brown dress shoes
1. Chocolate tasseled loafer 2. Chestnut double monk strap wingtip 3. Tan Wintip lace up

For some reason men always struggle when choosing the right brown dress shoe.  Not only is shape a struggle, but finding the right shade of brown can be a difficult task as well. I’ve always found it interesting how the shade of a brown dress shoe can completely change the setting the shoe was made for. So here’s the rundown on brown:



Khaki is strictly a summer time colour. It’s so light in color that it really only compliment other pastels and pale tones in your wardrobe. Consider a khaki shoe for a beach setting.



Tan is a slightly darker tone of khaki but has a little bit more of a dressier feel because of it’s shade. Like khaki it’s a warm weather colour but it doesn’t look inappropriate when paired with tailored pieces.



Chocolate brown is your 4 season shoe colour. It’s light enough that it doesn’t look inappropriate at a summer wedding but dark enough to be worn to the office. With the right style, like the tasseled version above, it can be worn both casually with jeans or formally with a suit.



Chestnut is the darkest of the bunch and is strictly a formal color due to its slight red color. From galas to business meetings, a chestnut brown is both subtle and prominent at the same time.

When it comes to cost it all depends on how you plan on wearing your shoes and where you plan on wearing them. However, here are some tips to look for when purchasing. Make sure they are 100% leather inside and out. Leather molds to your foot and this increases comfort. Also, go for a wooden sole instead of a rubber one. A wooden sole is a good indication of a well-made shoe. Not only do wooden soles add to the overall look of the shoe, they also extend the shoes lifetime.

Stay tuned for part 2 of The Essentials List: Footwear.

Yours truly,

Mr. Cavaliere