A Simple Guide To Men’s Shoes

Which shoes to wear

When buying a pair of shoes, quality is key.

Shoes are an investment, because not only will you look stylish, but you also have to keep in mind the comfort of your feet.

You don’t want to hurt your feet with wearing cheap shoes.

Though one can argue that not everyone can afford really expensive ones, it is better to have two high quality shoes rather than having six low quality ones.

Truth is, you don’t need that many shoes, you just need a couple versatile, high quality ones.

So, how should your shoe locker look like?

Depends primary on the weather.

You want to have different shoes for different weather.

You cannot wear boots in the middle of summer, just as you cannot wear moccasins and sneakers in the middle of winter.


So, without further ado, here are the essential pieces of footwear needed for a gentleman to look as stylish as possible without breaking the bank:
  • Sneakers

Sneakers are always a good idea for your jeans + t-shirt combination. You can even pair sneakers with jeans and shirt as well for a very casual outing. Other than that, keep the sneakers away from more formal occasions.

Sneakers should be worn in the summer and excluded from the wardrobe for autumn, winter and spring, since they are white and light and will get dirty quite easily as well as not keeping your feet warm enough.


  • Moccasins

Moccasins ( or loafers ) just like sneakers, should be worn in the summer. As the weather gets hotter in the summer you do not want your feet to sweat and smell, so avoid leather ones and opt for suede moccasins. If you opt for white sneakers, there is no need for white moccasins as well, so pick blue, navy or brown ones for different styles and combinations.

  • Oxford shoes

The Oxford shoe is the most basic and timeless piece one can have. You should only consider plain toe or cap toe Oxford’s, as they are very versatile and can be worn in formal setting or more casual occasion.


The brown Oxford shoe is an excellent piece to have for a daytime outfit. You can also wear it while going out at night. But it is best if these are saved for daytime activities.

  • Derby shoes

Derby shoes are somewhat less formal than Oxford ones. And although the shape is very similar, the difference is that the Derby ones have an open laced structure. Just like Oxford shoes, consider plain toe or cap toe Derby shoes.

  • Double monk strap

Double monk strap shoes are very stylish and are something between Derby and Oxford in terms of formality, but without laces. You can wear them in casual setting or in a more formal one. Very versatile and have a stunning look when paired with jeans, pants or suits.

  • Chelsea boots

When winter knocks on the door, these types of boots are your preferred choice. Very elegant, very stylish and will keep you warm at the same time. The elastic siding allows for these boots to be put on and taken off with ease.

  • Dress boots

Of course, if you are not into Chelsea boots yourself, you can always opt for a standard dress boot. They are simple, basic, will keep you warm and make you look stylish at the same time.


Depending on your style and preference pick shoes that match your intentions. You don’t have to buy ten or twelve shoes to have many combinations. 

For summer, opt for a pair of white sneakers, navy and brown moccasins.

That makes it three pairs total for the summer.

For autumn or spring, opt for a pair of black Oxford or Derby shoes for formal occasion or going out at night.

Pick a pair of brown Oxford or Derby or a double-monk strap for less formal events or during day time activities.

That is two pairs total for autumn or spring time.

For winter, opt for a pair of standard dress boots and one pair of suede or leather brown Chelsea boots.

That is two pairs total for the winter.

Not only will you keep your shoe locker to a minimum ( having combined a total of seven pieces of footwear for all four seasons), you would have bought high quality shoes that also make for a very versatile wardrobe.

The Gentleman

A young, enthusiastic man with a passion for fashion, healthy lifestyle and a constant need for improving myself. Having enjoyed ( and still enjoying ) the benefits of my current lifestyle, I am dedicating my time providing short, insightful posts and tips on how to become a better man.