Oxford shoes
The venerable Oxford, also known as a "Balmoral," sets the design standard for men's dress shoes. Its sleek lines and subtle styling look great with almost any casual or formal outfit. It's the most versatile dress shoe a man can own, so if you're in the market for your first good pair, then dark brown Oxfords are exactly what you need. Take special care not to confuse these with Derby or Blucher dress shoes which are often falsely advertised as "Oxfords" (especially in America where this distinction is less often made).
The defining characteristic of an Oxford is what is referred to as "closed lacing." With closed lacing, the lace tabs are sewn underneath the vamp (the upper part) of the shoe rather than on top of it as is the case with open lacing. Closed lacing results in a clean silhouette and a slimmer shape, making it more formal, whereas open lacing is decidedly more casual.
Derby shoes
If the Oxford is the father of the dress shoe family, then the Derby is the more laid back — although far more popular — uncle. What sets them apart is all in the lacing: Whereas the Oxford has the lace tabs sewn under the vamp (i.e. closed lacing), the Derby shoe features three-piece construction with two-quarters of the shoe, including the lace tabs, sewn on top of the vamp. This results in a more casual style known as open lacing.
This can get confusing as the distinction between the Oxford and the Derby is blurred by some shoemakers, especially in the United States. Many shoes with open lacing are sold as "Oxfords," and this is likely due to the popularity of the Derby style as well as more lax dress standards in America (wear a pair of brown shoes — especially Derbies — in London's business district during working hours and you might get some disapproving looks).
Chelsea Boots
Often associated with European style and the British "Mod" subculture, dress boots might seem a bit foppish to many men today. Contrary to this perception, however, is the fact that the dress boot is a very traditional choice that predates the modern dress shoe. In centuries past, boots were, in fact, the norm, slowly giving way to dress shoes worn with ankle spats, which themselves gave way to the exposed-ankle footwear we wear today.
The only fundamental difference between a boot and a shoe is that a boot has a longer shank that extends up past the ankle, and many dress boots are simply Oxfords or Derbies with a taller shank. Certain styles, on the other hand, are almost entirely unique to dress boots. The two most common of these are the Chelsea and the Jodhpur, neither of which use laces. Chelsea boots feature elastic on the sides to slip onto the foot. Jodhpur boots are based on traditional riding boots and feature a strap-and-buckle closure.
Little-known trivia: White Chelseas were also featured in "Star Wars" as the footwear of Imperial Stormtroopers.
Monk Strap shoes
The modern monk strap is a relative newcomer to the men's style scene, and admittedly, reactions have been mixed: Men either seem to love these laceless shoes or think they are a youthful fad. You'll have to decide for yourself if monk straps are for you, but there's no denying their growing popularity which doesn't seem to be waning any time soon. Somewhat ironically, the monk strap — while considered a younger style relative to classics like the Oxford — actually has its roots in medieval Europe, where shoes with buckles were quite common.
The defining feature of the monk strap is right there in its name. This shoe's design is similar to that of the Jodhpur boot in that it forgoes laces in favor of a strap-and-buckle closure, which offers a unique modern look that is simple and sophisticated. They're definitely the most fashion-forward of the picks on our guide, but monk straps enjoy a dedicated following for a reason — this stand-out style really does look great. Those medieval monks must have had pretty good taste.
Wingtip shoes
When someone says "wingtip shoe," you might get a Great Gatsby-style vision of the Roaring '20s complete with flappers, gangsters, and men clad in double-breasted peak lapel suits. That would be a mistake, however: Wingtips are enjoying another go in the spotlight today, undergoing a revival in popularity among men who are, largely thanks to the web, re-discovering the classic styles of days gone by.
Your grandpa likely owned a pair of wingtips and it's time to give this style another go-around. The name "wingtip" refers not so much to the actual style of the shoe, but rather to its styling; a wingtip can be an Oxford, a monk strap, a dress boot, or another type of shoe. A wingtip is simply any shoe that features a punched pattern, known as brogueing, that forms a wing-like shape one the front of the toe box.