The Ayomipo Guide to Men’s Dress Shoes. 👞

Most people have heard Steve Harvey’s “Every man should have five suits”. 

In the video (either Mr Harvey’s or several of the “covers”), the idea is for men to have a core wardrobe— a versatile wardrobe that doesn’t require breaking the bank and one that gives men the freedom to combine pieces without much thought, knowledge about colour combination, much planning, etc and still look good.

My goal here is to propose something similar for men’s dress shoes.

A core “shoe rack” that works for all formal and business casual events including work, conferences, business meetings, church, etc.

Perhaps first an introduction.

Dress shoes are really formal shoes. These are the types of shoes men (ideally) wear with at formal events— weddings, interviews, work, funerals, etc). Sometimes when the dress code is “smart casual’ dress shoes can be worn too. Traditionally, dress shoes contrast with athletic or sports shoes like your tennis, sneakers, etc.

So if you are a man and you go to formal events such as your 9 to 5, where you are expected to wear shirts tucked into trousers, you should wear dress shoes except your 9 to 5 is done in a studio somewhere painting abstract portraits, in which case you’d better go in there barefoot and bare chested so you can better channel your inner Picasso 😄😄😄

For your first pair of dress shoes, you should either get 

1. A brogued wingtipped Oxford or

2. ⁠A plain toe derby without broguing. 

The choice will be determined by how many formal events you have in the week.

If you are new to the dress shoe business then I need to “interpret my tongues”

Oxford and Derby shoes are quite similar except that oxfords use a closed lacing system and Derbys an open one.

But pictures explain this best.

There you have an Oxford and a Derby.

Now, that you know the difference between oxfords and derbys, what is a “brogued wingtipped Oxford”?

“Broguing” refers to the perforated ornamentation found on shoes. In the past, it served a real purpose as gentlemen while riding their horses through swampy or wet areas would drain their shoes through these perforations however now, since it exists solely for “fashion”.

“Wingtip” describes the decorative toe cap of the shoe. The vamp of a shoe could either be plain or divided into two with the part over the toe either a cap or with ‘wings’ whose ‘tips’ extend from the front to the sides of the shoe.

Brogued wingtipped Oxford 

Oxfords are more formal than Derbys, but embellished shoes are less formal than plain ones— so plain toed Derbys or brogued wingtipped Oxfords are similar in terms of formality. 

So both are fine for your formal events and can be dressed down for business casuals too. Although, the Derby has just a tiny little bit more relaxed feel when worn, so strictly speaking the Oxford is the more formal of the two.

The second pair of shoes should be the second of the two above. If you have a brogued wingtipped Oxford, then go for a plain derby and vice versa.

Plain toed Derby

For the third pair, I’ll encourage you to get a dress boot. Few things elevate a man’s appearance  like a pair of dress boots! And you can totally wear this even with your casual pair of jeans! 

Leather Boots

And you can choose whatever type of boots you want — either a wingtipped or a cap toe. As long as they are traditional boots not all those contraptions with several buckles and flaps and all what nots…

The fourth item, should be a proper Oxford. Preferably a Plain Oxford or if you prefer something more contemporary, a cap-toe.

Captoe Oxford. Plain

These are the kings of the shoe hill my friends! These are the classic dress shoes. Either one you get will be the most formal of your shoes and ideally will be worn for the most formal events— weddings, funerals, convocations, inductions, royal college membership ceremonies, award events, et cetera.

For the fifth item, there are at least three options — 

1. A Chukka boot

2. ⁠A Chelsea boot

3. ⁠A Penny Loafer

If you are the agbada/danshiki/ buba ati shokoto wearing type, please don’t wear laced shoes on these! That’s the ultimate fashion faux pas — and you can tell your faves you heard it from me. Lolzzz… Instead pair these out-of-Naija formal wear with your Penny loafer. I know these days many people wear their native garments with sneakers and other sports shoes; it’s a clear contrast isn’t it? wearing agbada and sports shoes. Is it basketball you wear agbada to play or badminton? Fashion evolves I know but this kind of behaviour is more telling I suppose of our search for the elusive fountain of youth than fashion evolution.😄

Penny Loafer

For those who are the more “business casual” types a Chelsea or chukka boot will be appropriate. 

I you want to emphasise the business in business casual, then go for a Chelsea boot, otherwise a chukka boot (especially one in less formal colours of black or brown) will work if the  casual is more important to you.

Now I have actually gone to this length for three reasons—

1. to give men a basic framework informing their shoe choices

2. to try my hands at fashion writing… hopefully me too can hammer this 2025 from content writing

3. ⁠so all the sisters complaining they don’t know what gifts to get “brother” can hear this good news, repent of their evil ways, and be liberal. After all, it is the liberal soul that will be made fat.

If I have achieved any of these things through these updates, àbùse bùse niyen or as the English  will say, “fine and dandy!”