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Classic Shoes Every Man Should Own

There are two simple rules when it comes to your shoe collection. The first: having a versatile range to cover all bases. The second: Sticking to the classic styles. Whatever your look, whatever your budget and what ever's in the diary over the next 12 months, if you invest in a pair of well-made shoes in each of the following timeless styles, you’ll be covered for any occasion.


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 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 staple. It’s an undeniable classic that will never go out of style.

Once you’ve got loafers in your wardrobe, the next step is learning how to rock them with style and swagger. Casual loafers can be worn with denim and khakis, and sockless with shorts during warm seasons. If you’re dressing them up, style them with a blazer or and stick to dark colours and high-quality materials for a refined finish.


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. The perforations were designed for functionality and durability in wet terrain. The design has since evolved and the small holes are now mostly for decorative purposes. In fact, it is this detail that brogues are now renowned for.

The beauty of the Brogue is its versatility and effortless appeal. You can rock a pair with jeans and a button-down right through to tailored suits and formalwear. Brogues are also a great staple for your business attire.

Monk Strap

The monk strap shoe was, you guessed it, originally made for European monks as a more formal dress shoe alternative to sandals. Their buckle was to ensure secure placement on the foot and they originally had steel toe caps to give them protection.

Pair your Monk Strap shoes with a formal trouser or with a suit. For more detailing, roll up the cuff of the trousers so that the buckles of monk shoes are shown fully. For a more casual look, style your shoes with a V-neck t-shirt, fitted blazer and jeans. Suave.

Boat Shoe

Like their name implies, boat shoes were first created for sailors. As the story goes, in the early 1930s, Paul Sperry, an ardent sailor, and boater took his dog out for and was amazed by his grip while running across the ice. Upon closer examination, he realised the cracks and grooves on his dog’s feet formed a herringbone-like pattern that gave him grip. Sperry then formed the idea of cutting similar patterns on the soles of the shoes he used while boating.

Today, the soft leather moccasin-toed loafer-style shoe has made a mark on modern style. Being both presentable and sophisticated, this shoe offers the support and comfort of a trainer, while displaying a mature look to any outfit. Style your boat shoes with shorts and a T-shirt for a casual look or something more formal with chinos and an Oxford shirt.

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