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The Shoe Guide

A handy glossary for different types and styles of men's footwear, from casual shoes to dress shoes, including their various parts.

1. Brogues - Brogues take their name from the Gaelic word bróg, meaning “to pierce a piece of leather with an awl.” The original brogues were practical deerskin shoes worn by rural men as they tramped across the rain-sodden moors of Ireland and Scotland. Those shoes had holes punched into the uppers so that any water that got inside the shoe could find its way out when the wearer took his next squelchy step.

2. Cap toe - The cap toe refers to a piece of material, such as leather, covering the toe of a shoe as well as the means of reinforcing or decorating it. Think of the cap-toe oxford for example: a classic business shoe.

3. Cedar Shoe Trees - The single most important favour you can do for your shoes, other than provide proper cleaning, is to invest in a pair of unvarnished cedar shoe trees. Put them in when you take your shoes off at the end of the day. The natural wood absorbs moisture, which stops the leather from cracking, while the shape of the tree helps prevent creasing.

4. Chelsea Boots - Invented in mid-19th-century England as a short ankle-high riding boot for women, the chelsea boot offered a great innovation: a side panel of elastic that made it much easier to get on and off than a laced riding boot. In the 1960s, the style was taken up by men into the mod scene, especially when The Beatles and their imitators started to wear them. Now as elegant and convenient as ever, they are a wardrobe staple.

5. Chukka Boots - Named for a chukka, the period of play in a polo match, chukka boots originally were ankle-high suede riding boots with short laces and only two or three eyelets on each side. Today the design has been adapted and can look very smart when made of polished leather, great with a pair of casual trousers and something of a statement when worn with dress pants.

6. Derby - These more informal shoes go by many names, including bluchers, bucks and Gibsons. Originally commissioned for soldier’s kit, they slowly made their way into men’s country and hunting wardrobes due to their construction, which is more rugged and waterproof than oxfords. Derbies are easily distinguished from oxfords as the vamp is sewn over the throat of the shoe, and the laces are placed on top.

7. Desert Boots - Desert boots, stylish but informal, have been with us since World War II when British officers stationed in Egypt paid cobblers in the Cairo bazaar to make simple ankle boots out of undyed suede with rubber crepe soles. English mods adopted them in the 1960s and they have drifted into and out of fashion ever since. Though they stand up to spring and fall weather, they are also lightweight enough for summer. And they’re versatile, looking equally great with jeans, chinos or corduroy pants.

8. Drivers - Driver shoes are aptly named; they are shoes meant for driving. Typically they are an adaptation of a slip-on moccasin: lightweight, flexible and comfortable. They often have an extended rubber sole that curls up the back to protect the heel and back of the shoe.

9. Espadrilles - Espadrilles may have originated in the 14th century, but they still look fresh every summer. Their distinctive jute sole and canvas upper make them perfect for casual wear. Developed for the climate in the south of France, espadrilles keep the feet cool in every sense of the word.

10. Loafers - The very name conjures up notions of informality and comfort – and laziness. Did these shoes really catch on because men were too lazy to bend down and tie their laces? Some experts believe loafers originated in Norway, made by off-season fishermen, before sharp-eyed tourists brought the pattern back to the U.S. in the 1930s. Others point to the moccasin made by First Nations peoples. Either way, penny loafers became a central part of American culture in the mid-20th century.

11. Monkstraps - Monk straps really are inspired by the footwear worn by monks – most probably by 15th-century Franciscans in the Italian Alps. Halfway between a lace-up, a slip-on and a sandal, they are fastened by a single or double strap that crosses over the instep to be buckled on the side. Monk straps offer a delightful alternative to the dress boot, their versatility complementing both the suit and casual trousers.

12. Overshoes (Galoshes) - Overshoes, or galoshes, are protective rubber slippers worn overtop shoes in wet or snowy weather. Galoshes do offer the advantage of keeping the soles dry and are designed not to slip in icy conditions.

13. Oxfords - Thirty years ago, a man knew what was meant by the term “dress shoes.” They were the lace-up shoes he wore with a suit – sturdy, plain and designed not to stand out. Oxfords were always “closed laced” – in other words, the two parts of the upper that are drawn together by the laces were sewn underneath the front part of the shoe. Classic oxfords still follow that pattern, made with an undecorated vamp, stitched welts and (often) leather soles. They may or may not have a toe cap, wingtip or brogueing.

14. Sneakers - Originally designed for sports and other forms of physical exercise, sneakers today are an integral element of a man’s refined, casual wardrobe. The term generally describes a type of footwear with a flexible sole made of rubber or synthetic material and an upper part that is made of leather or synthetic materials.

15. Wingtip - The wingtip shoe has a toe cap with a backward extending point and curving sides, resembling the shape of a wing.