Shoes. Man. Its almost a cliche by now that your shoes tell a good part of your story. You're out, you see a beautiful woman and quickly flip through your mental folder of lines to see which one she's most likely to respond to. Got one. Cool...you walk over to her and she looks you up and down really quick like. Eyes pause on your shoes and right there, doesn't matter what you say, she's already shot you down. Now you're wondering to yourself, "what just happened?" I'll tell you what just happened. Those shiny square-toed joints you got on your feet happened.
Whether you're wearing a rare pair of Nike Jason Vorhees Dunk Highs or a pair of bespoke Edward Green double monk-straps, your shoes can make or break your look. Most men I know hate shopping for shoes, or any kind of shopping for that matter but I strongly recommend that a man takes the time to check out the many options when it comes time to acquire a new pair of shoes because there are so many differences in styles. Taking this time to learn the basics can help one avoid buying a pair of shoes that are too trendy, too cheap, too uncomfortable. A good pair of shoes, should last years with the proper care. Start here and then head over to "The Discerning Gentleman's Guide to Shoes." Let's get into it...
The Brogue is a style of low-heeled shoe or boot traditionally characterized by multiple-piece, sturdy leather uppers with decorative perforations (or "broguing") and serration along the pieces' visible edges. The brogue as we know it today is said to have originated in the United Kingdom, specifically Scotland and Ireland that was constructed using untanned hide with perforations. Brogues were traditionally considered to be outdoor or country footwear not otherwise appropriate for casual or business occasions, but brogues are now considered appropriate in most contexts. Brogues are most commonly found in one of four toe cap styles (full or "wingtip", semi-, quarter and longwing) and four closure styles (oxford, derby,ghillie, and monk).
Shown: Paul Smith Miller Washed Brogue.
An Oxford is a style of laced shoe characterized by shoelace eyelet tabs that are stitched underneath the vamp, a construction method that is also sometimes referred to as "closed lacing". Oxfords first appeared in Scotland and Ireland, where they are occasionally called Balmorals after the Queen's castle in Scotland, Balmoral. Most shoe stores in U.S. will refer to Oxfords as bal-type opposed to blucher-type or in simple english, "lace-ups."
Oxfords are traditionally constructed of leather and were historically plain, formal shoes but are now available in a range of styles and materials that complement both casual and formal forms of dress. The toe cap can either be lined with two narrow rows of stitching, perforated holes along the end cap stitching (quarter-brogue), perforated holes along the end cap stitching and on the toe cap (semi-brogue), or a semi-brogue with the classical wingtip design (full-brogue).
Shown: Allen Edmonds "Vernon" Oxford
The Monk Strap...
The monk strap is a style of shoe with no lacing, closed by a buckle and strap. They are normally found in either a single strap or a double strap. When it comes to dress shoes, the monk strap is like that cousin that rarely shows up to family events because they don't quite mess with everyone because it's not exactly a loafer or a lace-up. The shoes history is that it was popular with monks in Europe because it was more protective than the sandals they normally wore and it was easy to take on and while still functioning as a solid work shoe. The construction of a monk strap shoe is similar to that of a blucher, with the quarters overlapping the upper vamp or tongue of the shoe, rather than meeting in the middle to be laced.
Most menswear enthusiasts agree that the monk strap ranks right between oxfords and derby's when it comes to dress appeal. Speaking of appeal, the fact that most monk straps can work well with a suit or denim makes them very attractive to a lot of men.
Shown: Edward Green Westminster Double Monk Straps in Dark Oak Antique
Chukka boots or turf boots are ankle-length boots with two or three pairs of eyelets for lacing. They are usually made from calfskin or suede, although they have also been made from more exotic materials such as crocodile. They were popular in the late 1940s and 1950s as casual wear. The first chukka boots were called chukka because they resembled boots worn by polo game players who played in six-minute timed matches called "chukkas."
Sometimes other boots are mistaken as chukka boots because many shoes other than chukkas have the low style ankle. If the boot has more then three eyelets it is not a true original chukka style of boot. Chukka boots, like other shoes, have a throat in addition to the shoe tongue. The throat is the part of the boot that you slip the foot through to put on the shoe. A form of chukka boots worn by British forces in the Western Desert Campaign of World War II are Desert boots. Desert boots have a crepe rubber sole.
Shown: Peal & Co. Brown Suede Chukkas for Brooks Brothers
The Boat Shoe...
Boat shoes (also known as deck shoes or topsiders) are typically canvas or leather with non-marking rubber soles designed for use on a boat. A siping pattern is cut into the soles to provide grip on a wet deck, the leather construction, along with application of oil, is designed to repel water, and the stitching is highly durable. Boat shoes are traditionally worn without socks.
Modern boat shoes were invented in 1935 by Paul Sperry after noticing his dog's ability to run easily over ice without slipping. Using a knife, he cut siping into his shoes' soles, inspiring a shoe perfect for boating and a company called Sperry Top-Sider. Sperry Top-Siders are still a popular brand of boat shoe today, among many others, including Sebago and Timberland.
Boat shoes are used by sailors, as the name suggests; however, since the 1980s they have become fashionable footwear in America, the UK, Portugal, Argentina and France. Some boat shoes today have traditional white, non-marking soles, though many others today have dark non-marking soles.
Shown: Sperry Original Boat Shoe
The Driving Moccasin...
A driving moccasin (driving moc) is a contemporary version of the traditional Native American moccasin with the addition of rubber tabs on the sole. The addition of rubber-pad sole adds to the versatility and longevity of the shoe while maintaining the flexibility and comfort of a traditional moccasin. Driving moccasins are popular for both driving, walking and wearing around the home. Due to their flexibility and comfort, they are an ideal shoe for a long drive.
There are many variations on driving moccasin sole styles varying from manufacturer to manufacturer. The two most common styles are:
Rubber-dotted - These have a uniform covering of small, round rubber pads.
Separated Pad - These have larger, flat rubber pads separated by only small areas.
Shown: Tod's for Ferrari - Gommino Suede Driving Mocassins
The Saddle Shoe...
The saddle shoe is a low-heeled casual Oxford shoe, characterized by a plain toe and distinctive, saddle-shaped decorative panel placed mid foot. Saddle shoes are typically constructed of leather and are most frequently white with a black saddle, although any color combination is possible as a Google search will turn up.
Saddle Shoes first surged to popularity in the 1950s. Saddle shoes were considered to be a rather sporty shoe and were worn like loafers in the years before sneakers really became fashionable. They were and are still not considered a particularly dressy shoe for men but work well on more informal occassions where a sport jacket may be worn. Saddle shoes have made a big come back especially with the "preppy" crowd.
Shown: Alden x Leffot Cigar Saddle Shoe
The Penny Loafer...
In 1933, the Spaulding Leather Company turned out its version of the loafer. The G.H. Bass shoe company introduced the original version of what we now call the Penny Loafer in 1936, calling it the Weejun. The name refers to the flat slip-on shoes worn by Norwegian dairy farmers.
John Bass began producing loafers that had a strap across the top of the shoe for style purposes, as a loafer is traditionally defined by having no buckles or laces. This strap had a split design that was supposed to look like a pair of lips. This opening in the strap was soon used as a way to add a decorative touch to the usually simple loafer and small objects, such as pennies, were often placed there. A stylistic embellishment that had once been peculiar to Bass’s shoes became synonymous with an entire fashion. In the 1970s, the shoes became an essential part of the Preppy look. Bass introduced a slimmer version of the shoe called the Dover Weejun in 2009. The penny loafer is the ultimate classic shoe.
Shown: Alden Penny Loafer
Legal Disclaimer: The information and images provided on this page were compiled from various sources online. I do not purport to own any of the materials above unless expressly stated.