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Most casual, comfortable summer shoes possess a long and deeply practical history, often deriving directly from indigenous, unisex clothing crafted from local materials. Here are a seven that you might encounter on your travels.

1. Espadrilles: for when life’s a beach
The espadrille perhaps represents the essence of summer dressing. Raffishly bohemian, loochely leisured, they can add a dash of casual elegance to your summer footwear.

‘Defining summer ease, espadrilles were famously worn by Cary Grant in To Catch A Thief, tiptoeing silently across Riviera rooftops…’
Generally soled with jute rope (and some rubber and likely synthetic) but originally with esparto grass, this slip-on shoe arose 700 or so years ago in the Pyrenees, the footwear of peasant farmers. Variously known as alpargatas, espardeynes (in Catalan) and espartenas, the shoes were renamed ‘espadrilles’ by Riviera high society in the early 1900s which had adopted them for its relaxed resort life. Defining summer ease, espadrilles were famously worn by Cary Grant in To Catch A Thief, tiptoeing silently across Riviera rooftops and Grace Kelly (who Grant starred with in that movie). Other famous wearers included Pablo Picasso, Salvador Dali (who wore his tied at the ankle), Coco Chanel, Ernest

Hemingway, Bogart & Bacall, James Mason and Jack Kennedy. In photos, all look incredibly chic yet relaxed and nonchalant.
So, there’s every reason to consider espadrilles today as a summer fashion staple, an elain alternative to flip-flops or sandals. Lighter and cooler (in every sense) than trainers, they also allow your feet to breathe – which a canvas/rubber-soled shoe won’t. In fact, fans say that they make you feel like you’re walking barefoot. They are usually inexpensive, though beware of cheap Chinese factory versions; instead, look out for classic brands (such as Castañer) still made authentically by hand in Spain/the Iberian Peninsula – preferably from an old artisan shop in Barcelona’s Gothic Quarter: your homage to Catalonia.

Style advice: The golden rules are not to wear espadrilles in the city – preferably just on the beach or boardwalk – and only in very hot weather (never in the rain which is not good for those jute rope soles) and never, ever with socks. Pair with longer length casual shorts or linen trousers (perhaps white, slightly cropped or rolled), as Picasso or Dali would have worn them, or rolled and a well-fitting T-shirt or Breton top. And buy them on the small side as the canvas will stretch. It’s entirely permissible to ignore the heel and wear as slippers.

2. Loafers: perfect for loafing
The loafer, what we consider today to be the classic non-tying, slip-on shoe, has its ancient origins in the frozen north. It’s really a formal moccasin, and it’s the moccasin that has given rise to a slew of casual footwear, including the deck shoe. Here’s how.
The moccasin is one of the earliest unisex shoes – certainly the earliest footgear in North America – and the ancient ancestor of the loafer. Early fur traders and explorers in 17th century New France (Quebec) adopted the Native American deerskin design but reworked in oiled cowhide. The one- (or sometimes two-) piece construction afforded mobility and protected from the elements – with no sole-line stitching to allow water to seep in.

By the late 19th century, styles were being sold as ‘camp moccasins’, and exported to Europe – though something very similar already existed in rural Norway amongst the Sami (Lapp) people.

In 1936, American shoe company Bass (which had been making camp moccasins since 1876) brought out a Norwegian variation of the loafer shoe: ‘Weejuns’, short for ‘Norwegian’. And the style took off.The term ‘loafer’ was applied at some point in the 1940s and proved popular with teens in the 1950s and 1960s. It was only marketed as men’s semi-casual wear from the late 1950s, with Gucci’s becoming a staple in both men’s and women’s wardrobes through the 1970s and 1980s.
Loafer variations have included the ‘penny loafer’ or ‘penny moc’ where a penny could be slipped under the vamp strap, tassled styles, and Gucci’s signature equine harness hardware.

Style advice. Loafers sit at the more formal end of the casual shoe spectrum. How best to wear? What to put it with? Try pairing with blazer and slacks.

3. Deck shoes: all ship-shaped 
Leather deck shoes also emerged from the moccasin (see loafer section above). The ‘Top-Sider’ was devised by Paul Sperry in 1935 as a boating shoe, with brown leather upper and rubber sole to grip the deck. Sperry had almost died slipping off his own boat and was inspired to devise a secure boat shoe by watching his dog walk quite effortlessly on deck – the gripping grooves in the rubber emulated those on his dog’s paws. Top-siders became an official shoe for the US Navy during WWII, and through the 1960s and 1970s the Kennedy clan were photographed wearing them on holiday, giving rise to an iconic American look that ultimately developed into what we’d call ‘preppy style’ today – epitomised by designer Ralph Lauren (see Olympics 2016 opening ceremony post).
Style advice. Deck shoes have certainly made the transition from deckwear to streetwear, but tread warily. Though ubiquitous in the ‘80s, that nautical look can be a hard look to pull off, and you risk looking like a fish stranded out of water if you are over-nautical in a land-locked (particularly urban) location.

‘Long before sneakers, Brazilian Indians used to waterproof their feet by dipping them in liquid latex tapped from rubber trees.’

4. Sneakers: the original sports soles
Long before sneakers, Brazilian Indians used to waterproof their feet by dipping them in latex tapped from rubber trees. But sneakers, or plimsolls, as we know them today emerged in the 1860s when low-cut, lace-up canvas uppers were first joined to rubber soles, giving rise to the effete generic style of the ‘croquet sandal’ or ‘tennis shoe’. In 1876, the Liverpool Rubber Company began producing a rubber-soled shoe, marketed from 1885 as a ‘plimsoll’ – because the red rubber sole resembled the famous red line on the ships’ hulls. By the 1890s, various rubber-soled shoes were being produced, mostly in the US and Canada, the term ‘sneakers’ appearing as early as 1894.
The Ked, introduced in 1917, became the first commercially marketed sneaker in the US – its name combining the Latin for foot (‘ped-’) with ‘kid’. The Converse All-Star arrived in 1919 as a high-top boot, the forerunner of all athletic shoes. And how hard it is to imagine the hipster uniform today without the Converse sneaker…

Today, not all canvas shoes are created equal. If you want a substantially soled sneaker, you might consider Converse, Keds or Vans (established 1966 in the US); white ones can look particularly natty – when new and clean, of course.

Style advice. But when is it really OK to wear sneakers? What colours? Cotton socks? What trousers? Sweaters?

5. Flip-flop: just tomorrow’s flotsam?
The world’s most ubiquitous footwear, the flip-flop has a very simple construction: just a sole and a Y-shaped strap. Flipflops seem to have originated in ancient Egypt circa 1,500 BC. But in the modern era, the flip-flop returned with US soldiers from Japan post-World War II – in the form of the zōri, a traditional straw sandal. The flip-flop became a firm unisex casual summer favourite from the 1960s, though the onomatopoeic name (derived from the distinctive foot-slapping noise a pair makes while worn) doesn’t seem to have entered American or

British English until the 1970s. Barak Obama became the first US president to be photographed in flip-flops while holidaying in Hawaii in 2011.
‘the flip-flop returned with US soldiers from Japan post-World War II – in the form of the zōri, a traditional straw sandal’

Style advice. Though the Dalai Lama is a frequent flip-flop wearer (and has had audiences with several US presidents while wearing them), flip-flops are generally viewed as just a step too far in the direction of comfort for even smart-casual purposes. And though toed socks may be available, we would generally advise against going there.

6. Birkenstocks: indulge your inner hippie
Moving on from the classic leather sandal, this German orthopaedic brand found firm favour with the flower people of the late 1960s. The Birkenstock’s signature contoured cork and rubber footbed, typically featuring a chunky upper with double buckled straps, is possibly one of the healthiest summer choices for your feet.

Style advice. Follow the rules for classic leather sandals. It’s advisable to stick to classic brown leather, despite the plethora of designer options out there. They can look presentable with longer khaki shorts, or rolled casual trousers, or neat chinos and a well-fitting polo shirt. But be warned: they will most certainly make your feet look a lot bigger.

7.Desert boots: hot-foot from the Sahara
Less formal than a hard-bottom but more dressed-up than a sneaker, desert boots make an interesting summer-wear choice with a less structured suit or sporty separates. Clarks claims the desert boot as its invention, Nathan Clark having brought the simple, minimally structured design back from his experience in the Middle Easter during WWII. The style celebrated its 65th anniversary last year.Check out John Mills in Ice Cold in Alex, treading gingerly through a desert minefield in his sandy boots.

Style advice. Desert books can ably plug the gap between casual and formal; think of them as a deconstructed formal. You can have some fun with the range of colours available, but avoid going over-patterned.

Casual shoe opportunities abound for your late-summer relaxation. Here, comfort is certainly king, but one should remain wary of committing the worst sartorial crimes. So, no flip-flops in the office or espadrilles on the underground, please, even in August.And what about health? Be aware that unstructured shoes can have an impact on your posture. The total absence of support in the flip-flop, for example, can present a problem for some wearers – particularly over prolonged periods or after walking any distance. In summary, it’s wisest to wear the most relaxed styles only when you intend to relax to the fullest possible extent.

Bibliography: Shoes, Linda O’Keeffe, Workman Publishing, New York, 1996The Seductive Shoe, Jonathan Walford, Thames & Hudson, 2007

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