//5 Classic Shoes Every Man Should Own

5 Classic Shoes Every Man Should Own

Check out these 5 classic shoes every man should own. Here at Idle HQ we’ve whittled it down to 5 key styles that we think you should have in your wardrobe this and every season. 

Check out more Men’s Style Guide features.

Some of you may be at that age when wearing a pair of trainers to go meet your mates down the pub simply isn’t cutting it. Of course, classic shoes have been around a few hundreds of years, but what you need to get your head around is slotting them into your everyday look to build up a stylish and timeless wardrobe.

Here at Idle HQ many of us have a bit of a sweet spot when it comes to classic shoes as many of us own a few pairs. However, we know that many out there don’t share the same feeling, and that’s what we have to change. There are, of course, many styles of shoe out there for you to have a go with, but here at Idle HQ we’ve whittled it down to five key styles we believe every man should own.


The loafer is a classic shoe that is a personal favourite of mine. They can be worn s quite literally any situation and work well. The loafer didn’t start life out as a men’s footwear mainstay, its origins stem from the Native Americans who invented the first version of the slip-on shoe called the moccasin. It wasn’t until mid-1800’s that shoemaker Raymond-Lewis Wildsmith developed the slip-on shoe for the landed gentry and the royal family as a house shoe.

From the foot of the royal family to the feet of the everyday man, the loafer has been through it all. It was in the 1920s and 30s when men started to wear the loafer to city lounges in America. Since then the loafer crept its way up to the more formal stakes and we now see it as both a formal and casual piece of footwear.

loafers mens street style
PHOTO CREDIT: Syndicate Details

Of course, there are many versions of the loafer for you to choose from, but we’ve narrowed it down to a few styles and a select few brands that seem to know what they’re doing what it comes to this classic slip-on shoes.

Key Brands:

We can’t talk about classic shoes without mentioning the good ole penny loafer now, can we? First invented my Mr. G.H.Bass himself when he saw a Norwegian farmer sporting a form of slip-on shoe to herd cattle in. Bass developed this shoe with a strip of leather across the front with a diamond shape cut out (for the penny). No-one really knows where the name ‘penny loafer’ comes from as no-one knows why the term was coined (no pun intended). But what we can agree on is that this pair from G.H.Bass & Co in black is spot on.

If you’re after something a little different then why not give these horse-bit loafers from Gucci a whirl. Guccio Gucci developed the horse-bit loafer after he worked in the famous Savoy hotel in London. He noticed that people staying at the hotel (who were of a certain caliber) loved the equestrian lifestyle and so wanted to incorporate that into his shoes. This brown pair is spot on as their silhouette and colour make them one versatile piece of footwear.

G.H.Bass & Co Weejuns Penny Loafers , Gucci Horsebit Loafers, John Lobb Tasselled Loafers
SHOP: G.H.Bass & Co Weejuns Penny Loafers


The origin of the brogue is unknown, no-one really knows who made this classic shoe up as nearly all the nations in the UK claim ownership of it. What we do know is that the shoe was made to be worn in the country in the fields whilst hunting.

The intricate design and perforated holes in the leather were made so that water and air could escape the shoe if it ever found itself in a puddle. Up until the mid 20th century, brogues were not considered a formal shoe, and to wear them for occasions other than country walking was frowned upon. They came mainly in brown, due to their practical and country origins, but they were developed in black when it became acceptable to wear them for business.

brogues mens street style

Key Brands:

For a more traditional pair of these classic shoes then why not give this pair from Churchs a go. The classic silhouette and style make them one versatile and smart shoe for this and every season. Handmade in the heartland of England in the shoemaking capital of the world, Northampton, these shoes will last you a lifetime and look stylish all at the same time.

If you feel you’d get more use out of a brown pair of brogues then try this Grenson pair on for size. Slightly less rigid then the pair from Churchs, as they are more of a casual shoe, they will work for both formal and casual occasions. Brogues can be quite a heavy piece of footwear, but this pair from Grenson are designed to be lightweight so you can wear them all day long without your feet getting tired.

Base London Davy Chunky Brogue Tan , Grenson Brogues Brown, Churchs Brogues Black
SHOP: Base London Davy Chunky Brogue Tan


The derby shoe is another classic that goes back a few decades. The great thing about this shoe is its simplicity and knack for always being modern and stylish. The derby shoe, or blucher as it’s sometimes known, is made up of only a few piece of leather and minimal stitching to keep it simple and sleek.

Its origins come from both American and the UK as during the 1850s men would wear them to go hunting. By the turn of the 20th century, however, the derby shoe became appropriate to wear in town as well as the country. So you see, all of these classic shoes started life out in the mud and dirt of the country before they became a fancier and more formal shoe.

derby shoes mens street style

Key Brands:

For a shoe with a little bit of difference then why not try this dark blue pair from Edward Green. Their classic silhouette and minimal design make them the perfect accompaniment to a smart-casual look this season. Teamed with a pair of dark grey trousers and a white button down dress shirt, you can have a cracking formal look with a small hint of detail on your feet.

For those of you who are on a budget then give this black pair from Base London a whirl. Their simple and minimal design makes them the perfect work shoe for those of you who are after a smarter look for the office. The red interior adds that little bit of hidden detail making them the perfect shoes for the office this and every season.

Edward Green Derby Shoes, Edward Green Derby Shoes Blue, Base London Derby Shoes Black
SHOP: Base London Derby Shoes Black

Monk Strap

Probably one of the lesser known shoes out there but the monk strap shoe is one of my personal favourites as it’s a little bit different and adds some detail to your look. The monk strap shoe was, you guessed it, originally made for the monks as a more formal dress shoe alternative to the sandal. Their buckle was to ensure secure placement on the foot and they originally had steel toe caps to give them a little bit more protection.

The structure of the shoe isn’t too dissimilar to the traditional oxford shoe, so you can see why they became more and more popular over time as an alternative to the oxford shoe. These days the monk strap shoe has taken on more variants than I care to mention, but what we can all agree on is that they’re as stylish as ever.

monk strap shoes street style

Key Brands:

  • John Lobb
  • J.M. Weston
  • Churchs

You can two options when you’re picking out a pair of monk strap shoes: you can either go for a double monk strap or a single monk strap. Either way, they still look stylish. This brown pair from John Lobb is spot on as their silhouette and darker brown colour gives them a more formal feel than a lighter shade of brown. Worn with a dark navy suit for a different yet stylish formal look this season.

For a single monk strap look that’s still full of style then try these J.M. Weston monk strap shoes. Their colour and shape give a more formal look whilst still being a classic looking shoe with all of the style needed. Worn with a pair of black slim-legged trousers and a white button-down shirt for a spot on formal look this season.

John Lobb Monk Strap Shoes Black, John Lobb Monk Strap Shoes Brown, J.M.Weston Monk Strap Shoes Black

Chelsea Boots

The Chelsea boot is probably one of the most notable and favourite pairs of shoes on this list, so it’s best to save them for last. The Chelsea boot was originally made by royal shoemaker J. Sparkes-Hall who created the boot as a house shoe for Queen Victoria. The elasticated sides and high silhouette made for a comfortable alternative to the rigid shoes of the time.

Over the years the Chelsea boot made its way onto the feet of men and women across the country as comfortable alternatives to their normal rigid dress shoes they were used to wearing. The boots made it over to the equestrian side of life when they became an alternative to the knee-high riding boot, again, as a more comfortable alternative.

Speeding into the 20th century the Chelsea boot made its way to the Kings Road in London (this is where they got the name ‘Chelsea boot’ after the famous London borough) where the young and trendy sported them as fashionable boots, and in particular bands such as The Beatles wore them almost all of the time.

chelsea boots mens street style

Key Brands:

  • Churchs
  • Edward Green
  • J.M. Weston
  • R.M. Williams
  • Grenson

When it comes to Chelsea boots there is a whole world of choice out there. For a more casual pair then why not try this brown suede pair from Grenson. Perfect for teaming with a pair of casual jeans and a simple tee for a day out or you can dress them up for the office with a dark grey flannel suit.

For a more formal pair of Chelsea boots then give this pair from Churchs a go. The smooth black leather gives them an instant formal feel whilst still being stylish. These are a great pair of Chelsea boots to own (I actually own this pair myself) as once you’ve broken them in I couldn’t think of a more comfortable shoe to wear.

R.M.Williams Chelsea Boots Brown. Churchs Chelsea Boots Black, Grenson Chelsea Boots Sued Brown

And On That Note

Classic shoes are the way forward for the man who is starting to grow up with his style. It doesn’t matter what background you’re from you can always sport a pair of classic shoes and look stylish at the same time. Forget the connotations of looking like an old man, some of the most stylish men on the planet all rock a pair of loafers from time to time, so grab a pair and get walking.

If you’re more of a brogue or derby kinda guy then I don’t blame you. Classic and comfortable is the way forward here. Originally designed to be worn in the country, these two shoes are perfect for that classic edge to a modern look. Monk Strap shoes are something a little different. Originally made as a dressier alternative to sandals for the monks these shoes have the same design and framework as the derby shoe. The choice is yours whether you want a single or double monk strap, either way, you’ll still look stylish.

Or, if none of the above tickle your fancy then try and sport a pair of Chelsea boots for a classic and timeless feel. The choice is up to you whether you want a smooth black pair for more formal occasions or keep it casual with a brown suede pair.