Know your shoes

Craig of That Dapper Chap tells us everything we need to know about the difference between the various styles of men’s shoes

Any dapper gent worth their salt needs great shoes. He also needs to understand his shoes to ensure that he wears the right shoe for the right occasion.

Confused about the differences between an Oxford and a loafer? Unsure what a kilted brogue is? Unsure if you need Monk straps in your life? Worry no more, That Dapper Chap is here to help and tell you everything that you need to know.

Blogger tells us the difference between mens shoe styles

Mens shoes are available in a wide range of styles but can you tell which each style is?


If you’re looking for a formal shoe for the office or a smart occasion Oxfords are the way to go. They tend to be very plain, unobtrusive and inoffensive. They are a very neat lace up shoe, and the section with the eyelets for the laces is sewn under the top section of the shoe. They may come with or without a toe cap and tend to be available in black and brown more than other colourways. A black tie event may call for a pair in patent leather for impeccable elegance.

Influencer tells us the difference between different types of mens shoes

Oxfords: Patent black leather from Cheaney. Brown leather from Cheaney and Oxfords with a toe cap from Next


Another great formal option, a Derby only really differs from an Oxford in that the section that contains the eyelets for the laces is outside and not stitched under the top section. Again they can come with or without a toe cap.  Both Derby and Oxford shoes can come in patterned leather or with brogueing and other details, so they don’t need to be plain if you fancied something a little more interesting.

How to tell the difference between Oxford and Derby shoes

Derby’s: black leather ‘Rutherford’ Derby shoes from Barker. Barker ‘Benedict’ and Robinson’s ‘chester’

That Dapper Chap describes the types of mens shoes

Me wearing Oxford shoes in brown suede by White Stuff


Sometimes referred to as a moccasin, loafers are very on trend right now, particularly in warmer weather. Worn with suits, jeans or shorts and with or without socks, they offer a versatile range of looks. Essentially they are a slip on shoe and can be found with bars across the top, tassels and sometimes a kilt.

The first shoe below has a kilt as mentioned above. This is a length of fringed fabric attached to the shoe across the upper. Not exclusive to loafers, you can also find a kilt on brogues, Oxfords and Derby’s.

Know the difference between loafers and brogues

Loafers: Tan suede kilted loafers with tassels from House of Hound at Topman. Black leather tassel from Loake & Cheaney Penny Loafer

Influencer describes the different styles of men's shoes

This is me wearing a pair of burgundy penny loafers from Next


Like loafers, drivers are a slip on shoe with the main difference being that while the traditional loafers has a flat sole, a driver has a heavily textured rubber sole to help the shoe grip the pedals of the car. A casual shoe and available in a wide variety of colours and fabrics, these are great for holidays, worn with shorts and a printed short sleeved shirt. Like loafers, they can have tassels or metal bars across the top, but traditionally they have a threaded lace. Sometimes referred to as a Moccasin.

Influencer shows the difference between loafers and driving shoes

Drivers: beige suede from Office. Orange suede from Dune and Blue leather from Base London


Brogues are a lace up shoe, more formal than not and can come in Oxford or Derby style. Their defining factor is the patterned punching. Very traditional, and again very on trend, they’re also great as boots. Usually found in black and brown leather you can now find them in various colours and in suede also. It’s also quite fashionable to get your leather brogues tattooed!

Know the difference between mens' shoe types

Brogues: Brown suede from Cheaney. Navy leather from Hammond & Co at Debenhams and glossed brown leather by Grenson

tattooed brogues

Tattooing your brogues is very on trend right now. Tattooing by Oliver Sweeney

Bloggers confirms the differences in men's shoe designs

Me teaming a green Topman suit with burgundy leather brogues

Chukka Boots

Chukka boots are essentially an ankle boot, usually made from suede or leather and have laces. Ones with a crepe or rubber sole and made from suede (often referred to as desert boots) tend to suit more casual looks and look good with jeans. Plain leather boots with a leather sole can be worn with a suit or smarter look.


That Dapper Chap tells readers the difference between mens shoe types

Chukka Boots: All available at Debenhams online

Influencer shares details on how to tell the difference between mens shoe styles

Wearing my White Stuff chukka boots on a trip to the beach

Chelsea Boots

Unlike chukka boots, Chelsea boots have no laces and usually have elasticated side sections (sometimes a zip) to allow the wearer to put them on and remove them. The also have a loop at the back to help you pull them on. Available in leather and suede and a variety of colours, these are also very on trend currently.

Influencer shows the differences in men's shoe styles

Chelsea Boots: Loake brown suede, Black leather from Hammond & Co at Debenhams and brown leather from Cheaney

Blogger shows how to style chelsea boots

The Chelsea boots I’m wearing here are by Hammond & Co at Debenhams

Monk Straps

A monk shoe or a monk strap shoe, also referred to sometimes as a pair of monks or double monks, are shoes with no laces that are fastened using buckles. They are a more formal shoe and tend to be available in black, tan or brown. They can be found with a single buckle or two (hence double monks)

Blogger shows the difference in men's styles of shoes

Monk Strap Shoes: Loake, Red Herring and Loake. All available at Debenhams

Influencer wears double monk strap shoes

Yours truly wearing a pair of ‘double monks’ in tan leather

Sandals, Flip Flops & Espadrilles

All of these are very casual and are suitable for hot weather. Wear them around the pool or on the beach.

By far my least favourite types of footwear, and something you will never see me wearing are flip flops and sliders. I detest them. Even a sandal is offensive to me and I much prefer to wear something more ‘filled in’ such as the red Cano Shoe sandal below.

Flip flops, often in rubber or leather are formed of a flat sole with a toe post and a V shaped strap that sits on top of the foot. They are okay to wear pool side or on the beach but other than that I cannot stand them.

Sliders are similar to flip flops but have a single thick top strap.

Blogger details the different types on men's shoes

Sliders, red leather sandals by Cano Shoe and leather flip flops

Traditional sandals tend to be available in plastic, rubber, canvas or leather and have a strap across the top of the foot and another around the ankle. Often fastened by velcro or clips and are another shoes that I find somewhat offensive.

Espadrilles on the other hand are more acceptable to me as a casual holiday shoe. They are filled in and are very plain, they have small elasticated sections at the sides to alow the wearer to put them on and remove them easily but they are defined by their woven sole.

Blogger tells us the differences between the types of mens shoes

Traditional sandals, Espadrilles and rubber flip flops

Influencer wears red leather sandals by The Cano Shoe Company

Wearing the red leather ‘Benito’ sandals by The Cano Shoe Company

Boat Shoes

Also known as a deck shoe, boat shoes traditionally have a ‘moc-toe’ like a moccasin/Loafer and a lace that threads around the back of the shoe. They come in canvas or leather and are predominantly coloured blue or brown, although I have seen other colours including white and yellow. They offer a causal, more nautical look, as the name may suggest.

Traditionally they had non marking soles, so as to not mark the the boat while sailing the riviera. I would wear these sockless with shorts or with socks and jeans or chinos.  Add a Breton stripe sweater and a woolly hat for the full nautical look.



Blogger tells us th difference between mens shoe types

Boat Shoes: Timberland, Loake and Hammond & Co, all available at Debenhams

a nautical look with white boat shoes

I hope that you’ve found this post useful and that you are now armed with all the knowledge that you need when selecting your next pair of shoes whether they be a kilted brogue, a suede tasselled loafer or a brown leather boat shoe. Just promise me that you’ll avoid flip flops!

Feel free to leave me a comment to let me know your thoughts. I’d love to hear from you.


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