A brief history of the loafer
Originating in Norway in the 1930s, this moccasin-style slip-on was soon adopted by visiting American tourists and championed by the US magazine Esquire before being originally produced for the US markets under the name 'weejuns' (as, in 'Norwegians').

When to wear the loafer
Outdoors summer business meetings, golf games, garden parties. The loafer is known for its exceptional comfort.

When not to wear the loafer
Funerals, weddings or any highly formal event. Not a good look.

What to match with the loafer
If it's a hot summer's day, match a pair of loafers with classy Bermuda shorts and polo shirt - and ditch the socks. If you're wearing them with long trousers, use either dark socks or - if you're feeling daring - none at all. But never, ever wear white socks (too Thriller-era Michael Jackson). And never wear with jeans.

What the loafer says about you
That you're easy-going, approachable and a lover of life.

A brief history of the Chelsea boot
Used for horse-riding in Victorian times and known as jodhpur boots, this ankle-high boot with elastic sliding witnessed a rebirth in the 1960s British mod scene.

When to wear the Chelsea boot
Perfect for a spring or autumn stroll or evening out, the Chelsea boot adds a touch of retro classiness to a casual outfit.

When not to wear the Chelsea boot
Sticky summer days - no matter how cool they look (think of your poor feet) - and hardcore business meetings.

What to match with the Chelsea boot
The Chelsea boot looks great with tapered jeans or cords and a chunky knit jumper or polo neck and leather jacket. Always wear with a narrow legged trouser.

What the Chelsea boot says about you
You're stylish, edgy and sophisticated.

A brief history of the brogue
Starting life in the highlands of Scotland and in Ireland, this heavy leather shoe was traditionally seen as a country shoe, patterned with punch holes, or brogueing, to allow good drainage in the boglands. They're also known as 'wingtips' in America due to the distinctive 'w' pattern of the brogueing on the toe.

When to wear the brogue
Once seen as solely appropriate for country jaunts, the brogue has now been embraced as one of the most versatile of shoes, pretty much acceptable everywhere.

When not to wear the brogue
Could raise a eyebrow at the most formalised of business meetings or evening events.

What to match with the brogue
Best with a heavy, dark fabric suit or even paired with dark overdyed denims and a chunky jumper.

What the brogue says about you
You're solid, earthy and reliable.

A brief history of the Oxford
Originating in Scotland and Ireland, the Oxford was historically a relatively plain formal shoe, but now can be found in both seamless and cap toe variations, and sometimes with minimal brogueing.

When to wear the Oxford
The Oxford is perfect for business events, wedding receptions and swanky evening dos - a snappy must-have for every gent.

When not to wear the Oxford
Best avoided for muddy country trekking and ill-advised disco dancing on slippery floors.

What to wear with the Oxford
Couple the Oxford with a dark toned suit or smart black trousers and a crisp white formal shirt for a timelessly classic look.

What the Oxford says about you
You're timelessly stylish, sussed and sophisticated.

A brief history of the Derby
Initially popularised in the 19th century, the derby shoe was originally open-toed but for the last century has been far more similar to the more common Oxford. The distinguishing feature of the derby, in contrast to the Oxford, is that the laced facings are unstitched at the bottom.

When to wear the Derby
Arguably slightly less formal than the Oxford, this exceptionally comfortable design classic will still work a treat at classy restaurants, boardrooms and members' clubs alike.

When not to wear the Derby
Playing with the kids in the park - you don't want to scuff these babies - and hiking through woods.

What to wear with the Derby
This versatile number will work equally well with a smart tailored suit or a cord and sweater casual look.

What the Derby says about you
You're dependable, traditional and stable.