Our favourite shoes styles for SS14 will see you through all manner of sartorial scenarios. In this week's menswear diaries discover the history behind each shoe, and why we're wearing them right now.


The Chukka boot is a casual boot which is ankle length and typically has a dog tail tab at each heel alongside just two or three sets of eyelets for lacing. Often crafted from leather or suede, the boot derives its name from the game of polo (Chukka denotes a period of play).

On Reiss: The Chapman Chukka boots' pale oatmeal hue makes them the ideal pair for wearing on days spent off-duty in the sunnier months.

Wear it with: Mid-blue jeans, a crew neck grey marl jumper and a petrol-hued technical fabric bomber jacket.


Although the tasselled loafer's appearance suggests a longstanding presence in menswear, the first recognisable iteration of the shoe was in fact made post World War II, far later than often assumed. Subsequently the shoe was adopted as a staple of 1960s preppy style, and the rest is menswear history.

On Reiss: Forgoing the traditional brown or tan colourway, the Anstice loafer offers up a thoroughly modern take of the classic shoe thanks to its deep navy colouring.

Wear with: A crisp white shirt and grey tailored trousers.


Another stalwart of preppy Americana style, the penny loafer's impressive versatility means that it can be dressed up or down, whatever the occasion. The penny loafer's provenance can be traced back to the 1930s, where it emerged as a fashionable shoe which mimicked the flat slip-on shoe style of Norwegian farmers. Although the company which devised the shoe's signature opening at its front band began to slip pennies into the opening, hence the retrospective 'Penny loafer' moniker.

On Reiss: Simple, sleek and stylish, the Theo penny loafers are crafted from pure leather, and are a streamlined take on a menswear icon.

Wear with: Sand coloured chinos and a colour tipped polo knit.


Designed by the eponymous world champion badminton player, Jack Purcell trainers have retained a near peerless relevance, feeling just as fresh now as they did way back in the 1930s when they were first created. Key design details include a canvas upper, a rubber sole, a ‘smile’ contrast tab at each toe, a distinctive light blue sole and Jack Purcell branding at each heel.

On Reiss: The classic style arrives at Reiss boasting all of those familiar design details which have kept the shoe at the forefront of men’s style for so many years.

Wear with: Slim-fit black jeans and a Cuban collar shirt.


Forgoing laces in favour of a buckle fastening, the single monk strap shoe is an elegant formal style. Aptly named, the monk strap shoe originated in European monasteries in the fifteenth century where monks eschewed laces in favour of straps. Thanks to the shoe’s high closure, the style creates an unbroken vamp which elongates the foot.

On Reiss: The Foster single monk strap shoes in brown are a streamlined, elegant pair boasting a supple leather composition.

Wear with: A black two piece suit, a crisp white shirt and a polka dot pocket square.


Instantly recognisable and subtly studded at the sole, the driving shoe may have begun life as practical footwear but thanks to an undeniably stylish appeal, the shoe has migrated from pedal to pavement. Inspired by moccasins, driving shoes are typically crafted from suede and feature threading detailing.

On Reiss: The Brooke driving shoe is a classic style crafted from luxurious suede but featuring contrast detailing.

Wear with: Pink tailored shorts, a pair of Wayfarer shades and a white crew neck T-shirt.