Pairs of Shoes Every Man Should Own

Pairs of Shoes Every Man Should Own

How many different styles of shoes does one need? It's the ultimate fashion question. There are so many styles and options out there, where do we even start? Fear not, we'll show you the difference between a Chelsea Boot and a Chukka Boot, and when to wear them. You'll also know what other styles you'll need in your wardrobe, and which shoes will pair perfectly with a men’s suit?

We have compiled this handy and helpful guide to help you sort out all of your men’s footwear questions. Here are the pairs of shoes you will need, and how to wear them.

The Chelsea Boot

A timeless classic and highly versatile in style, Chelsea Boots are ankle-high, close-fitting boots that typically feature an elastic side panel. This signature side panel makes them easy to slip on and off. Consider these boots your best friend—a sophisticated slip-on style, if you will. Not quite dress shoes or utility boots, Chelsea Boots are versatile and fit many occasions. We love how they elevate your style in more casual settings.

Pair them with jeans and a cardigan sweater for a casual but sophisticated look. Wear your leather Chelsea Boots to work or for a date night. You could also invest in a second pair of suede Chelsea boots for more casual weekend hangouts.

Dress Sneaker

Men's dress sneakers are a fantastic hybrid of casual shoes and more formal dress shoes. They are perfect for occasions when you want to stay casual, while still keeping a fashionable vibe. Wear them for occasions where wearing dress shoes might look a bit too formal or stiff. Think nighttime rooftop party or a dinner party at a friend’s house. With the bonus of being extremely comfortable, they might become your go-to shoe, great for running errands or hanging with friends on the weekends.


Trainers are the ultimate casual wear. These are your gym shoes or yard work shoes. Not to be confused with running shoes, which are made with a sole designed for impact, these shoes are for workouts at the gym including weight lifting. Alternatively, you could just wear these shoes around the house or on any non-work day because they are just so comfortable. Don’t forget to pair them with your men’s workout clothes to be comfortable, casual, and ready to hit the gym.

The Chukka Boot

The Chukka Boot is sometimes regarded as a slightly more formal variant of the Chelsea Boot. These boots feature laces, however. They typically have two to three eyelets and are usually made of calfskin, making them very soft and flexible. These shoes can be worn with your weekend wear, out on date night, or with your business casual attire to the office.


Another timeless classic, these shoes never go out of style. These are great shoes to have for elevating your relaxed style in the summer. Loafers can be worn with jeans or with men’s chinos to uplevel an otherwise casual style. They are best for warmer months and are typically worn without socks when worn with shorts.

The Oxford

Every man also needs a pair of Oxfords in his wardrobe. These are the epitome of formal. You may only wear these shoes a couple of times per year, but they are tightly laced, highly polished, and painstakingly designed—truly the ultimate formalwear. These are the shoes you want on hand to wear to a wedding or a black-tie gala.

Slip-Ons or Boat Shoes

Every person needs a casual slip-on shoe. Whether you keep them by the door for walking the dog in the morning, or they are your go-to shoes for everyday wear, you need a comfortable and casual shoe that is easy to take on and off for ease and convenience. You could go with a more youthful, easy-to-slip-on style that covers the top of your foot. This particular style also features rubber soles originally designed for skateboarding, which gives the ultimate casual, comfortable cool vibe.

For a more mature look, get yourself some boat shoes. These shoes also work great for casual outings but provide a different twist to your outfit. We love wearing boat shoes to the beach in the summer with men’s board shorts for a fun, relaxed, and casual look.

Whether you are in the market for dress shoes or something more casual, we hope this list has been helpful and informative, guiding you to your next men’s footwear purchase.


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