A Gentleman’s Guide to Classic Shoes

First impressions are formed in an instant, so make sure your choice of shoes doesn’t let you down.

Here’s our guide to classic shoes – the mark of a true gentleman.

Chukka boots

Perfect for Polo – Chukka Boots
Source: Eye Contact

It’s not surprising given the cost of running a string of polo ponies that Polo is a game for the super wealthy. The gentlemen who play probably wear handmade leather riding boots by English bootmaker Horace Batten. But don’t worry if you haven’t got access to old money or a banker’s bonus.

Chukka boots are named after the periods of polo play of the same name. Between chukkas, tired ponies are exchanged for fresh ones. Off the field, you’ll wear your chukkas for recreation.

Stylish, understated and elegant, they’ve been on trend since the second world war, when a crepe soled version of the Chukka was used in desert combat.

Boat shoes

Sail Away – Boat Shoes
Source: Luxury Yacht Charters

Yachting is widely known as a gentleman’s occupation, but even if you live in the West Midlands town of Meriden – the English town furthest from the sea – you can still wear boating shoes. Traditionally worn without socks, these moccasin style shoes were invented by Paul Sperry in 1935 as a non-slip shoe for leisure sailors.

They have been popular ever since – a truly classic men’s shoe. Ideal for those summer barbecues where you want to appear relaxed by don’t want to let your standards slip.

Chelsea Boots

Chelsea boots

Chelsea boots rock

For something a little bit more formal, you can’t go wrong with a pair of Chelsea Boots. Made famous by the Beatles, Chelsea boots have been around since the Victorian era. Back then they were simply called paddock boots or jodhpur boots and were mostly used for riding.

With their stretchy elasticated gusset, they’re easy to put on and take off, so perfect for visiting friends’ houses – especially those with a no shoes rule.


Brogues – Made for all seasons
Source: Hypebeast

The shoes with the holes, brogues occupy a unique place in the pantheon of classic British shoes. They’re formal enough for almost every occasion but worn in brown are also a great shoe to relax in.

Not all brogues are equal however. Quarter brogues are holed just on the toe cap, half brogues have holes on the toe caps and heels. The full brogue, or wingtip, has a pointed toe cap with wings extending down both sides.

For the ultimate style statement though – you’ll need a pair of spectator brogues. Constructed from two contrasting materials, no gentleman would be seen without them during the roaring 1920’s


Made to Last – Goodyear Welted Soles
Source: Style Salvage

For a formal but relaxed look, the derby shoe is the right choice for the aspiring gentleman. A classic lace up, the derby is also known as a Blucher – but not if you’re English.

For longevity, go for a pair of shoes with a Goodyear welted construction. This allows them to be re-soled, so you won’t need to throw them out just as they’ve moulded to the shape of your feet.


Dress to impress – Formal shoes for job interviews
Source: Ddanzi

For all formal situations from funerals to weddings and job interviews, the Oxford, is uniformly accepted to be the most appropriate footwear. True conservatives will go for a simple parallel stitched toecap – but brogued is fine too.

And the good news is – these classic men’s shoes look just as good with jeans as they do with a formal business suit.