Our Guide to Smart Shoes

What makes a shoe 'smart'? Is it the smooth, quality leather, or maybe the impeccably cut upper with its flawless stitching? Is it the quality of the cleated sole, or the polished finish? Actually, it's all of these – and more. At Charles Tyrwhitt, we're here to heel you properly, with shoes crafted from either Italian, French, or Portuguese leathers. Better still, every pair of our smart leather shoes for men comes with a long heritage of style, practical features, and ingenious design details.

Let us take you through our men's smart shoes for all occasions – step by step – from Oxfords to trainers via brogues.


Every shoe rack needs a pair of Oxfords – they simply set the standard for smart (if not, the smartest) footwear. The question isn't when to wear Oxford shoes, it's when not to. In iconic black, this bestselling style will see you from weddings to business meetings and interviews. Their enclosed laces give a clean and elegant finish, which shows off the smooth leather. The Oxford is named after the university, where 19th-century students craving comfort found low shoes easier to wear than boots.


You need to be a bit of a footwear aficionado to spot the difference between Oxfords and Derbies. Put simply, the Derby has open lacing, with the vamp left unstitched, while the Oxford lacing is fully closed. This means they're more adjustable – ideal for those with wider feet and higher insteps. Like the Oxford, the Derby is a formalwear classic to wear with your business suit or occasion outfit. Back in the mid-19th century, they were the trainers of their day, worn for hunting and riding as a lightweight alternative to boots.


With a wealth of different colours and cuts, there's a pair of brogues for every occasion. This design classic hails from the damp farmland of Scotland and Ireland ("brog" is Gaelic for shoe). Those signature perforated patterns were originally punched in to let out water when the shoes were worn in boggy conditions. The journey from field to fashion was completed when, in the 1930s, the Prince of Wales adopted brogues for sports such as golf.


On the smart-casual shoe scale, loafers sit in the middle. "What makes a loafer so distinct?" you might ask. Well, first it has to be the defined heel – this is what distinguishes them from moccasins. Second, the sole, which is completely separate from the upper. Slip-on loafer shoes for men are perfect for teaming with lightweight suits for summer… and they don't look out of place with shorts either. They first gained sartorial status in 1930s America and were based on shoes worn by Scandinavian fishermen. It's believed that the term 'Penny loafer' was coined when, back in the day, young men would insert a penny into their loafers for the bus ride home after a night out.


Sleek and polished Chelsea boots are Tyrwhitt's bestselling boot and make an elegant alternative to your Oxfords. This year-round style sits just above the ankle, with a signature elasticated panel on the sides. Chelseas started as 'paddock boots' for riding – even Queen Victoria sported a pair. When the Beatles brought them into mainstream fashion in the 1960s, the style was renamed after the Fab Four's achingly hip SW3 hangout. Few boots can boast such a diverse fan base.


More casual than the Chelsea is the Chukka boot. This modern classic has a rounded toe and laces with two or three eyelets. Chukkas sit closely against your ankle, so slip neatly under slim-fitting or tapered trousers – wear them with your suit for a relaxed look at the office during colder months. After being worn by British soldiers during the desert campaign of World War II, they became popular civilian wear. Why do desert boots share their names with a polo term? We think it's simply because they look a bit like riding boots…