A gentleman’s guide to classic shoes

Smart, brown, leather Derbys from Samuel Windsor are a versatile choice

Smart, brown, leather Derbys are a versatile choice
Image source: Samuel Windsor

First impressions are formed in an instant. Make sure your choice of footwear says the right thing about you with help from our guide to classic shoes – the mark of a true gentleman.

Oxford shoes

Polished Oxfords from Samuel Windsor will take you everywhere from interviews to weddings

Polished Oxfords will take you everywhere from interviews to weddings
Image source: Prestige Oxford shoes in black leather from Samuel Windsor

For formal situations like job interviews and weddings where a suit is required, a pair of smart Oxford shoes is uniformly accepted to be the most appropriate footwear. True sticklers for tradition will opt for a simple parallel stitched cap toe – but brogued Oxfords are a great choice too.

Think Oxfords are only for formal wear? Think again. Wear a pair of brown brogued Oxfords with your indigo jeans and top with your favorite shirt for a look that’s comfortable and casual, but still classy.

Derby shoes

Lightweight leather Derbys from Samuel Windsor can be laced tightly or loosely for a comfortable fit

Derbys can be laced tightly or loosely for a comfortable fit
Image source: Lightweight leather Derbys from Samuel Windsor

For a formal but relaxed look, Derby shoes make a great alternative to Oxfords in all but the most formal of settings. A classic lace-up, Derbys are also known as Bluchers – unless you happen to be British, in which case you’d be met with blank incomprehension.

For longevity, go for shoes that feature Goodyear welted construction. This special method of stitching the leather or rubber sole to the upper allows them to be resoled again and again. A favorite pair of quality Goodyear welted shoes could easily last you a decade.


Wingtip brogues from Samuel Windsor are suitable for smart and casual wear

Wingtip brogues are suitable for smart and casual wear
Image: Prestige Brogue with rubber sole from Samuel Windsor

The shoes with the holes, brogues take their name from ghillie brogues, the name for the shoes gamekeepers or “ghillies” wore when working on the great aristocratic estates of Scotland. The holes were originally to allow river and rain water to drain easily from the shoes.

Now broguing is purely decorative, and comes in several designs. Quarter brogues are holed just on the toe cap, while 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.

A fine pair of these shoes is formal enough for almost every occasion but brown brogues also look great for casual use. For the ultimate in style statements, we turn to the spectator brogue. Constructed from two contrasting materials, during the heady days of the roaring 1920s, no gentleman would be seen without them.


Brown leather penny loafers from Samuel Windsor look great with chinos

Brown leather penny loafers look great with chinos
Image: Loafers from Samuel Windsor

For a dash of European flair, don a pair of black tasselled leather loafers with your suit, or for more casual wear, a pair of brown suede penny loafers looks great with chinos or moleskin pants.

These versatile slip-on shoes come in black, brown, and blue, so there’s a style and color to suit all occasions. Leather is the smarter option while suede tends to sit toward the more casual end of the spectrum.

Chelsea boots

Black Chelsea boots from Samuel Windsor

An iconic shoe loved by British band The Beatles
Image: Prestige black Chelsea boots from Samuel Windsor

Made famous by The Beatles, Chelsea boots have actually been around since the Victorian era when they were simply called paddock boots or jodhpur boots and were mostly used for riding. Apparently, the British monarch, Queen Victoria, loved them because the elasticated gussets eliminated the need to fumble with button fastenings.

These days Chelsea boots lend your outfit sophistication. They look great with wool rich trousers, or dark jeans. For a bohemian edge, wear a roll neck sweater and top with a tweed or cord jacket.

Boat shoes

With non-slip rubber soles, boat shoes from Samuel Windsor are comfortable and safe

With non-slip rubber soles, boat shoes are comfortable and safe
Image: Classic boat shoe in navy and brown from Samuel Windsor

You don’t have to be a yachtsman to wear boat shoes. Traditionally worn without socks, these moccasin-inspired shoes were invented by Paul Sperry in 1935 who noticed his dog never seemed to slip on the ice. He cut tiny slices in the soles of his shoes – mimicking his faithful hound’s paw prints. The shoes quickly caught on and, because they also grip well in wet conditions, they soon became a favorite with leisure sailors.

A classic and very wearable men’s shoe, boat shoes are perfect for those summer barbecues and drinks parties when you want to appear relaxed but don’t want to let your standards slip.

Whichever shoes you decide to wear, make sure you buy quality footwear – like you, a decent pair of leather men’s shoes gets better with age.

Posted in Men's Shoes.

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