5 Dress Shoes Every Man Should Own

As men we often neglect the importance of the shoes we wear. Women will spend a month’s wages on a pair of heels to make a statement but the typical man will settle for a £30 leather pair similar to the shoes they wore at School.

I’m not saying we need to overdo it, I’m just trying to stress the importance of the shoes you wear.

We did a video about a year ago where we hit the streets of London and asked women what they liked on a man and over 90% of them said ‘good shoes’.

A good pair of shoes can really dress up an outfit I recommend you check the elevator shoes. Throwing on a well fitted white tee with some dark denim jeans may be casual when worn with sneakers, but wear it with a Derby Shoe or a Brogue and immediately your outfit is suitable for a bar visit or casual dinner date.

Even if your day to day style doesn’t require dressing up, it’s still important to own at least one of these 5 dress shoes I’m about to recommend. Whether it’s to dress up a casual outfit for a night out or to wear with your suit at a wedding, I highly recommend you have at least one of the below in your wardrobe.

In a nutshell, if you’re reading this and you still think you don’t need to own a good pair of dress shoes… you’re wrong. Re-read the first few paragraphs.


What Makes A Good Shoe?

Before we dive into the 5 dress shoes every man should consider owning it’s important to understand what makes a good shoe.

Shoes are an investment piece. They’re something I’d always recommend spending more money on than you normally would. Why? It’s simple. Cheap shoes look, well, cheap and they also wear a lot quicker.

You could head out after reading this and buy yourself a pair of Brogues for £40 ignoring what I’m about to tell you.

The £40 pair of brogues are made with cheap leather, they’re mass produced and the quality of the stitching and sole makes a Shoe Shiner squeal.

Because of the poor quality this cheap pair of shoes you thought were a bargain quickly wear and after 8 months of weekly wears they’re simply unwearable. You head out and buy another pair for £40.

Over the space of a few years you’ve probably spent £250+ on dress shoes alongside having to go through the hassle of shopping each time.

On the flip side a stylish man knows that a well-made, quality pair of dress shoes can last them up to 10 years and sometimes beyond. A Goodyear Welted Construction means they can be resoled when worn, and hardwearing leather will withstand all weather conditions.

You could invest £200 in a good pair of shoes that last you years from now or you could spend a little amount to begin with knowing that you’ll be shopping for a new pair soon.

I know what I’d rather do…


Here are a few things to look for in a good pair of shoes.

The Leather

Make sure it’s 100% leather. Pay attention to the thickness of the leather as well, with thicker leather often meaning it will be a more hard wearing shoe but may be less flexible. Try to avoid bonded leather which is typically made from leftover scraps that are glued and bonded together.


Don’t neglect comfort in return of the shoe being hardwearing. More modern shoes and typically ‘ready to wear’ shoes are often more flexible and take less time to ‘break in’. If you want to wear your dress shoes with more outfits it’s important to pay attention to the comfort.


Investing in a good pair of shoes typically means you’ll wear them for years to come, therefore concentrating on a style that will outlast the trends is important. All of the 5 shoes I recommend in this article are ‘timeless’, they’re shoes that have been around for centuries and will continue to be stylish in centuries to come. Investing £300 in a pair of blue suede shoes because they’re on trend right now will typically lead to you hoarding them away in the wardrobe once the season passes.

Well Crafted

Paying attention to how the shoe is made is highly recommended. I always recommend a Goodyear Welt Construction which can easily be resoled if they start to wear. Other construction methods such as the Blake may be cheaper and will make the shoe more flexible but it’s often less resistant to water damage and repeated wear.


Another thing to consider is buying directly from Shoemakers. There are a number of brands that focus solely on shoes and some of them have been producing high quality dress shoes for centuries. There reputation is built around the shoes they produce and they don’t just include them in a collection to boost sales.

I personally only buy shoes from specialised shoe brands such as John Lobb, Grenson, Crockett & Jones and Loake. 

So let’s dive in, here are the 5 dress shoes I recommend every man to own.

1. The Derby or Oxford Shoe

This shoe leans more towards to the formal spectrum but modern styles have made it a shoe that can be worn with casual attire.

Firstly it’s important to understand the different between an Oxford and a Derby, as both shoes have similar characteristics.

The key difference is the lacing system on both shoes, with the Derby using an open lacing system and the Oxford using a closed lacing system. A closed lacing system typically makes the Oxford a more formal shoe compared to the Derby which uses the open lacing system. Here’s a visual representation.


In terms of colour opting for a darker brown will make the shoe more versatile. Black leather tends to be more formal and tan tends to be more casual. Therefore opting for a darker brown will allow you to dress up or dress down the shoe.

If you want to use the Oxford or Derby for formal occasions only (as most people do) opting for Black leather will better suit.


2. The Brogue

This really is the go to shoe most men invest in as it can look great with a suit but also look great with jeans.

The brogue is a shoe that’s been stylish for decades and it’s main characteristic is the ‘broguing’ detailing you’ll find on the shoe. Originally the purpose of the perforations were to allow water to drain from the shoes, now the ‘broguing’ detailing is seen as more of a style statement and more modern shoes have taken a more decorative approach.


Again when choosing a brogue the same rules apply. Focus on the quality of construction, comfort and do your research. This again is a timeless shoe therefore it isn’t something that will come in one season and will be out the next.

In terms of colours a Tan will be the most versatile and will create a subtle statement. I often advise against Black leather for Brogues as they tend to be more of a casual dress shoe.


3. The Monk Strap

A personal favourite of mine, you really can’t go wrong with a Monk Strap shoe. This shoe bridges the gap between formal and casual again making it the perfect option to dress up some jeans or wear with a suit.

The monk strap shoe is another timeless yet versatile shoe, appearing as a registered design all the way back in 1901.

The two common Monk Strap shoes are the single monk strap and the double monk strap. Some designers have introduced 3 and more straps but realistically these will be more short lived.


The single monk strap is a cleaner more minimal shoe which is often great for formal attire, where as the double monk strap is my personal favourite. Opt for a shade of brown as it will make the shoe more versatile and even lighter shades of brown and suede if you want to create more of a statement.

You can add some Italian flair or what people like to call Sprezzatura to your outfit by leaving one strap unbuckled on your double monk strap shoes.


4. The Chelsea Boot

A more controversial choice this time, as the traditionalists wouldn’t class the Chelsea Boot as a ‘dress shoe’.

Personally I think the boot looks great dressed up or down so including it in this feature seemed fitting.

The Chelsea Boot typically consists of two parts made from a single piece of leather, the vamp and the quarters. They have a strip of elastic that extends to just below the ankle but not all the way down to the sole. They’ll have rounded toes, low heels and typically be made from leather.

Personally I’d wear Chelsea Boots with denim, having a small turn up to show the elastic detailing on the boot. They also don’t look out of place with a suit dressed down with more modern styles utilising them with tailoring.


5. The Loafer

Last but not least and probably the most versatile of them all, the loafer is a shoe you can wear all year round.

From the Gucci loafer to the Penny loafer your options are endless, but choosing the right style really is down to personal preference.


The loafer is a lace-less, low shoe which keeps the ankle exposed. The loafer typically exposes the socks you’re wearing or is often worn with no socks in the summer.

Tasselled loafers are something I’d personally recommend, and keeping it classic with G.H. Bass Weejuns is something I’ve recently invested in.

bass weejuns


How Many Do You Own?

So there we have it, 5 dress shoes I highly recommend.

Personally I’ve made space in my wardrobe for all 5, but investing in just one or two to start is highly recommended.

How many do you currently own?

Comment below and let us know.