Best Men’s Dress Shoes 2020

It’s a cliché I’m sure you’ve heard a million times before:

“Women can tell a lot about you by the shoes you wear.”

A bad pair of shoes can be a serious deal breaker.

I know what you’re thinking, it’s not like we don’t have enough to worry about already when it comes to attracting women right? It is what it is, so guys so let’s not disappoint the fairer sex and let’s make sure that we’re (literally) putting our best foot forward and that our shoes are saying the right things about us.

Whilst a lot of guys understand that women can tell a lot about us by the type of shoes we wear and that we should be wearing nice shoes. But what exactly are nice shoes? What colour and style are we meant to be wearing? The fashion world is a daunting place and can often leave the average fella feeling a bit overwhelmed.

But fear not gents for today I have a compiled a definitive guide to the best men’s dress shoe for 2020. I present you with my top five options to suit any type of date or situation which are all timeless designs which will work for any age group.

The general rule of thumb, and this can be applied to all areas of fashion, is when you have no idea of what to wear the safest bet is to go smart and classic. In men’s fashion when you want to impress, go smart and classic. If you have no idea what is cool, go smart and classic. Basically, classic smart casual wear is the easy way forward for the average joe. Footwear is no exception, so we have stuck purely to smart and smart casual shoes which by definition are going to be leather.

My Top Five Best Men’s Dress Shoes 2020

Chelsea Boot 2
Chelsea Boot
Chelsea Boot

The Chelsea Boot

The famous Chelsea boot, a favourite for any occasion that will go with almost any style. The Chelsea boot is versatile and durable. It oozes masculine vibes being a durable heavy boot whilst also being extremely stylish. They are best teamed up with jeans and a fitted leather jacket for a cool, casual look. We’ve shown a black version in the images above, but they look amazing in brown or beige and even in different finished such as nubuck or suede.

I mean it when I say this but every stylish man must own a good pair of Chelsea boots so go out and buy a pair now!

The Tan Brogue

Tan Brogue 1
Tan Brogue 3
Tan Brogue 2

The summer favourite. The tan brogue is crisp and dapper and definitely shows attention to detail with its defining feature being an elaborately decorated pattern on the toe. Match with a pair of fitted light blue jeans a light-coloured blazer and a white, salmon or sky blue shirt and a loud pocket square to be the dandiest date she will have this summer.

The Oxford

Oxford Shoe 2
Oxford Shoe 1
Oxford Shoe 3

The gentleman’s formal choice. Perfect for black tie or formal occasions the sleek shape of the oxford and separation detail on the toe adds a fashion element to a smart look. Make sure you shine at that wedding or event with a pair of these classics.

The Derby

Derby Shoe
Derby Shoe
Derby Shoe

Yet another British gentleman’s classic. The Derby is of the sale ilk as the oxford however it has a subtler rounded toe which makes it more favourable for casual wear. Perfect for jeans or trousers and a good replacement for those who don’t like the lavish pattern on the brogue. A great choice for the subtle dresser.

The Penny Loafer & Similar Variants

Weejuns A

Another great smart casual shoe the loafer can be worn with trousers or jeans and is particularly snappy for a cool date look when teamed with cropped ankle trousers, no socks and a plain black or white t shirt. This look literally screams style. Trust me – ask any woman and they will agree.

Weejuns 2
Weejuns 3
Weejuns 1

So, there you have it gents. Follow the tips in this blog post and your dress shoe game on point. You will find men and women admiring your fashion sense as you will stand out from the crowd. Women will be complimenting you, maybe not to your face, but certainly to their friends.

If you want further help with your fashion feel free to drop me an email at We can discuss how I can help you with your individual style so you can look #hotshit.

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