Men’s Formal Dress Shoe Guide

men wearing brown monk strap shoe and trousers
Formal Shoe Guide PHOTO CREDIT: Pinterest

Need a little advice on formal shoes? Then we’ve got you covered here at The Idle Man for all you need to know. 

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There are many types of men’s shoes, and getting the perfect look starts from the feet up. Feeling comfortable; physically and mentally in a pair of fresh shoes can completely update your style, and it’s important that you have the best quality shoes to suit your budget. It’s easy to find the best dress shoes for suits, but it’s harder to find ones that go with both casual and formal wear, without loosing their unique look.

In this guide we’ll show you five dress shoes, and run you through the dos and don’t of pulling them off, and keeping them looking their best.  The fact of the matter is a pair of trainers, no matter now nice they are, won’t cut it in all social situations, and having a good selection of smart shoes is the best way to be prepared for any situation.

mens formal shoes and coats street style


The Fit

The most important factor to take into account buying shoes is getting the right size. So how should dress shoes fit? Well formal shoes don’t give in the same way trainers do, so you want to get the shape and size right first time. Get your feet measured and get to know what you feel comfortable in. Some things to remember when trying out formal shoes is;

  • The ball of your foot should fit comfortably into the widest part of your shoe.
  • There should be half an inch space between your longest toe and the end of the shoe.
  • Your foot shouldn’t slip in your shoe, and if it is but you’re desperate for them, get yourself an inner sole to bulk it out.
  • Leather formal shoes will soften, but they won’t stretch in the same way that other shoes will, so your shoe has to fit perfectly when you first try it on.

Men Shoe Sizing Chart formal shoes fit


Formal shoes, whatever the style, need to be properly cared for in order to look their best. A scruffy pair of suede monk straps or a scuffed pair of oxford shoes is going to ruin any kind of formality that you’re going for, and give your outfit a less than finished look.


Most of your formal shoes will be in leather, and luckily there are hundreds of products out there to help you keep them clean and shined, and in a luxurious finish. A basic way to clean your leather shoes is;

  1. Remove your laces so you avoid getting any polish on them.
  2. Brush off any dirt on the shoes with a soft brush or cloth.
  3. Use a leather cleaner, or saddle soap and a little water, and rub your shoes in circular motions with a cloth in order to get rid of any scuffs.
  4. Polish your shoes with a cream polish, then buff off in circular motions with a separate clean cloth.



For suede, a suede brush is your best friend, as you can’t use the same kind of cleaning products on suede as you can on leather, so you options are a little more limited. It’s a good idea to brush your shoes after every wear to prevent any build up of debris, but always remember to brush in the direction of the nap. There are different ways your suede shoes can get dirty, so there are different ways to deal with the damage.

  1. If you get mud on your suede, wait for it to dry and then carefully chip it off, before brushing out the excess dirty with a suede brush.
  2. Scuff marks can be cleaned up with a suede eraser or rubber cleaning stone
  3. Gum can be removed by placing your shoes in the freezer until the gum freezes, then, like the mud, carefully chipping it off.
  4. Water stains are tricky to remove and it’s likely that your shoes will go a shade darker, but to create an even look stuff your shoes with newspaper and lightly spray them with water. Blot with a damp cloth and leave them to air dry.


It’s not intially clear when the oxford shoe first came about, but it was around 1825 that the popular ‘half boot’ shoe call the Oxonian was first reported. The style changed from a shoe with side slits designed for comfort, and a higher heel, to the classic formal piece we know today. Through their evolution they’ve become a shoe that’s easily worn with formal outfits, but that can also be paired with more casual pieces like chinos and smart jeans.


Although maybe people get oxfords and derby shoes confused because of their similar look, it’s the difference in their lacing design that makes all the difference. Oxfords have a closed lace system and brogues have an open laced system, which affects the overall look of the top half of the shoe and the gives the oxford a more compact, tighter design.

derby vs oxford closed lace open lace diagram

Although there’s no set rule on how to tie your oxford shoes, bar lacing is usually the neatest and most common way of finishing off your look. You can either have the end of your laces tied in a bow and displayed at the top of your shoes, or tied underneath the flap of your shoes and tucked away to give a clean look.

Smart Casual Look

Although oxford shoes seem to be set in a formal look, they were originally intended to be a more comfortable alternative to the high soled shoes of the day, and weren’t necessarily meant to be for smart occasions. It’s not a taboo therefore to mix them with more casual clothing pieces, and even jeans can get a look in when you’re matching your oxfords. It is important to remember though that while it’s possible to get a more casual look with these shoes, the look should never the less be streamline and neat, so avoid joggers and a long line top and go for more tailored pieces.

One outfit that’s easy to achieve, and creates a stylish and understated look is by pairing a simple slim line grey jumper over the top of a slim fit pair of black jeans, before finishing off with a black Harrington jacket. You can choose whatever oxford shoes you want with this, but a brown or burgundy will go well at creating a warmer contrast compared to the cool tone of the jumper.

mens dr martens burgundy shoes street style


Smart Look

The problem with styling a smart look with a pair of oxford shoes is how much choice there is. You can really go for a huge range of styles, as oxfords and men’s formal trousers go effortlessly well together, and a traditional pair of dark brown ones will go with various coloured suits.

One outfit that’s a simple classic is to pair a navy suit with a white shirt and brown oxford shoes. The white shirt adds a crisp contrast to the suit, while the men’s brown dress shoes compliments the navy trousers. It’s a timeless colour combination and suits every one regardless of age.

mens oxford shoes formal street style
PHOTO CREDIT: The Hanger Bay



Like most shoes with a broad history, no ones really sure exactly where the brogue first came from. There are hints that it originated from Ireland though, and it’s clear it was designed to be worn as a walking shoe, especially if the wearer liked trekking through bogs, from its additions that allowed water to drain freely from it. Over the years its design evolved, and it changed from something that was never intended to be worn in a formal way to one of the most recognisable dress shoes out there.

Brogues come in a few different styles, with some being sleek and with a smooth plain leather, while others have a thicker, chunkier design along with added detailing on the toe, or around the whole shoe. Whatever style you choose to go for, there are different ways to accentuate its look and ensure that your outfit looks clean, elegant and in keeping with the style of your shoes.


Smart Casual Look

Because of the broader design of these shoes, there are various ways to incorporate them into a smart casual look that relies less heavily on a sleek, finished appearance. You can go for various leg wear, such as chinos or jeans, however jeans will give a more casual look and allow you to experiment more with the top half of your outfit.

Choosing the right jeans is important however, and you don’t wanna go go for anything too loose and laid back. A good pair of cuffed straight leg jeans will give a tailored, yet informal look, and will allow you to easily pair it with a slim fit T-shirt. Alternatively you can go for a slimmer fit pair of jeans, again cuffed if you like, and choose a more formal top half, like a patterned oxford shirt to go with it. This will create a balance look that straddles the line between formal and casual.

mens brown brogues casual street style


Smart Look

Of course, brogues are more commonly worn in formal situations, so it’s important to know how to dress them up in a sharp, stylish way. If you’re wanting to achieve a smarter look, try to avoid brogues with a thick sole, and choose instead a more defined shoe. Polish up the leather and wear with a slim fit pair of chinos or trousers, pairing it with a smart shirt and, if the weathers gloomy, a matching blazer.

This is a timeless look that’s going to suit pretty much any body type, and if you’ve worn in those brogues enough then they’ll be soft and perfectly comfortable. For a splash of colour you can easily go daring with your socks and create a more dynamic look, but there if you’re not a fan of the look it’s easy to wear brogues with a pair of invisible socks for a cleaner, summer friendly look.

mens brogues formal look street style


Chelsea Boot

Although not the most common formal shoes, the chelsea boot is still something that can be worn in various outfits, from sophisticated smart looks, to more laid back casual styles. So how did the shoe even begin it’s life. Well it’s funny how many formal shoes started their days as walking boots. Chelsea boots started off in the Victorian times, and transitioned from men’s walking boots to a more casual, comfortable form of riding boots.

It was only really in the 1950s, when the creative socialites of London made them their uniform, that the newly named chelsea boot became a popular shoe for its appearance alone. Once the Beatles took hold of it the style sky rocketed, and everyone wanted to own a pair of these classic shoes.

The design of the shoe has changed slightly over the years, and some styles feature a broader, shorter heel that’s more comfortable and easier to incorporate into your wardrobe. You can also buy them in more materials, and although leather is still a popular choice, suede can give you a more subtle look.


Smart Casual Look

As a shoe that’s taken on many different looks, the chelsea boot can easily help rock a smart casual look, and is ideal for slipping on and finishing off pretty much any outfit (except obviously your gym wear, please don’t ever wear these with gym shorts…). Because of their close fitting look however they look best with more slim lined pieces, so if you’re going for a casual look with jeans, try choosing a pair in a slim fit design. Then it’s as easy as throwing on a T-shirt, and a long trench coat to complete an easy, stylish look.

mens Chelsea boots casual street style
PHOTO CREDIT: Rowan Row Blogspot


Wearing chelsea boots in a smart way isn’t as hard as it seems. If the Beatles managed it, so can you. The sleek design already lends itself to a formal look, so the trickiest part if making sure the shape and colour of your suit matches with your shoes. As we said before, brown and navy is a classic colour combination, so if you’re going for a light pair of brown chelsea boots, why not pair it with a sleek navy suit? If you want to go for a more traditional black suit though, a pair of black leather chelsea boots will compliment it perfectly.

mens suit and chelsea boots street style
PHOTO CREDIT: Plane Pretty


Desert Boots

The desert boots have a slightly more complex history than its walking shoe counterparts, and originated in the exotic landscape of the Egyptian desert (you might have guess that though from, well…the name). South African army lads who were sick of the tough boots they had to wear in the heat, commissioned a new pair of shoes to be made in a bazaar in Cairo. The new, tough, but light suede shoes became a hit, and after the war, Nathan Clark (recognise the name?) nicked the design and brought it back to showcase in America.

It was an instant hit due to its affordability and comfort, and it’s still a popular choice today because of its versatility but unique, stylish look. Remember to keep these suede boots looking their best with a little TLC, and, if you’ve got the money, try getting two or three pairs in different tones so you can dress up your outfits accordingly.


Smart Casual Look

Because suede gives such a subtle, gently muted look, it’s easy to make a pair of desert boots a staple item that can be worn with casual pieces. Keep the colours light, and mix a pair of slim fit jeans with a striped T-shirt, before pairing with some brown desert boots. You can try out different colours, but as brown is such as versatile colour it’s a good choice if you want to match it with a variety of tops and jeans.

mens clarks originals desert boots street style
PHOTO CREDIT: Clarks Originals


 Smart Look

It can be a little harder to get a smart look with these old school army boots, but their more delicate design does enable you to pull off a formal look, so if you’re choosing a light coloured suit, a pair of desert boots might be a good choice to go with it.

mens desert boot smart look street style

Men’s Formal Loafers

Now on to one of the most popular dress shoes for the summer; the loafer. There’s a seemingly endless supply of designs for this shoe, with tassel loafers, penny loafers, suede loafers and leather loafers, and all having their own unique history and stories behind the design and uses. The basic design was adapted from the Norwegian fisherman shoes, better known today as the boat shoes, and has taken on a different styles since then.


Smart Casual Look

For the summer time when plimsolls just won’t do, the loafer is a great alternative to slip on with a casual outfit. You can wear them with jeans and chinos, and for a less sleek finish a pair of more intricate tassel loafers are great for adding a bit of interest to your look. Try pairing a well fitted T-shirt with a pair of cuffed chinos, and slipping on a brown pair of tassel loafers for an outfit that can be worn time and time again with just a few variations.

mens g h bass co loafers street style


Smart Look

So it’s easy to pair loafers with a casual outfit, but it’s just as simple to work them into a smart look as well. Go for a darker leather penny loafer, which is more streamlined and elegant than a tassel one. Pair it with a classic black suit and tie and you’re all set. Avoid visible socks though, and keep your feet fresh with some trainer socks instead.

mens loafers smart street style


Men’s Formal Dress Shoe Guide

  • To ensure you get the most comfortable men’s shoes, make sure you get the fit right. Measure your feet and try the shoes on.
  • For the best formal shoes, classic brands like Hudson, Grenson and G.H. Bass & Co. are great.
  • Stick to brands like Dr Martens and Hudson for the best Oxford shoes.
  • Loafers are some of the best men’s shoes when you want a more casual or summery feel.
mens grey flannel shirt street style

On That Note

So there you have. You’ve seen some of the dress shoes that are easily incorporated into both casual and smart outfits, while still maintaining their classic look, and you’ve learnt a tad about their history. Caring for your shoes is the number one way to make sure you can pull off these looks, but it doesn’t take much to give your suede desert boots a little brush now and then, or polish up your leather brogues from time to time. The cut and finish of the clothes you wear your shoes with is also important, so be sure to wear something that not only suits your body, but also your shoes.


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Need a little advice on formal shoes? Then we’ve got you covered here at The Idle Man for all you need to know.  Read...
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