Kicking off our men’s shoe guide is the mighty Oxford (or a Balmoral for our UK blokes), probably the best-known type of dress shoe. The Oxford is a sleek, formal lace-up shoe identified by it’s “closed” lacing style and the appeal that the shoe is made from one piece of leather. The closed style means that the eyelet flaps on top of the shoe are stitched over the vamp, or the front section of the shoe, restricting the flap’s movement. Oxfords are usually worn in more formal situations, but can also be worn casually with a business suit. You might hear someone call this shoe a “closed front”, but it’s okay, you know they mean Oxford.

Often confused with the Oxford, the Derby is a close shoe relative, but not the same type of men’s shoe. Rather than having a closed lacing system like the Oxford, the Derby sports an open lacing system with the flaps being sewn under the vamp and not connected at front of the shoe. This style of stitching makes the flaps capable of movement and when laced the shoe looks as if it’s broken up into segments (top, side, back, etc.) Originally a sporting shoe, the Derby was used in more relaxed environments like hunting. Although a Derby could be worn in formal settings, it is more casual than an Oxford and could arguably make for a more comfortable, functional fit.

In the U.S., Derby’s and Bluchers are often used interchangeably to describe the open front lace style, but they’re actually two slightly different types of men’s shoes. If you pay close enough attention, you’ll see that Derby’s have the two sides sewn under the vamp, whereas Bluchers connect the two sides onto the vamp. Very similar, but it isn’t quite tomato/tomato.

Ahh, the Chelsea Boot. The favourited boot style of rock icons The Beatles and badass galaxy soldiers in George Lucas’ original Star Wars trilogy (yup, stormtroopers have a thing for Chelsea Boots). That easily makes it one of our favourites types of dress shoes as well. Originated during the Victorian era, but made mainstream cool in the 60s, this snug style of ankle boot is classified by its low heel, fabric tab on its’ backside and slip-on/slip off quality thanks to its elastic side panelling. Chelsea Boots have rounded toes and are versatile enough to be worn with jeans or a suit.

Identified by its wide heel and slip-on capabilities, the Loafer was inspired by mocassins; the shoe of choice for Native Americans. Like Oxfords, Moccasins come in a variety of lace-less styles (tassel, penny loafer, monk strap, etc.). Regardless of style, when it comes to the various types of men’s shoes, Loafers are generally considered to be the most casual. You can throw on a pair of loafers for a night on the dance floor with jeans or pair it with a suit – but we wouldn’t recommend loafers to wear anywhere fancy.

Brogue shoes are a style of Oxford, Blucher or Loafer that come with a perforated design punched along the edge of the leather overlapping the vamp. In short, Brogue is the style of shoes with the holes and thereby it’s own type of men’s dress shoe. But there are also types of Brogues and that’s worth distinguishing further. Hence we’re about to go all types of dress shoes within types of dress shoes on you, Inception-style. Here are the 3 most popular Brogue shoes:

Chukkas are a Derby styled ankle boot. Typically made from calfskin or suede, chukkas are created by using two to three sets of eyelets and an open lacing system to secure the quarters over the tongue of the boot.

Desert Boots are a type of Chukka, but Chukka Boots aren’t always Desert Boots. Confused? Ok, here’s the breakdown. Desert Boots were named after the light brown suede ankle boots the British soldiers wore during the desert campaign in WWII. Although very similar to the Chukka in style the different between Desert Boots and Chukkas is in their sole makeup. Desert Boots have a rubber sole and chukkas have a leather sole. Got it?

The Monk Strap style is defined as any shoe that uses a strap and a buckle instead of rather than laces to secure the foot in the shoe. When there’s a broader strap with two buckles, that’s called a Double Monk. Seems easy enough…

And capping off our men’s shoe guide is the boat shoe, which should be worn…well, on a boat. Before you start having Jay-Z fantasies about galavanting around on your 100-foot yacht, realize that boat shoes aren’t just a fashionable style of shoe, but they actually have a functional purpose. These shoes come equipped with an anti-slip rubber to accommodate walking (or partying) on wet decks. Usually, Boat Shoes (or Deck Shoes) come as Derbies or Bluchers in the Loafer style with the leather shoelaces tying over the tongue of the shoe. The typical Boat Shoe has a leather lace woven through the collar of the shoe and tying over the tongue of the shoe, to secure the shoe more tightly. Pair Boat Shoes with your most fitting yacht wear or pool clothes for a fashionable no-slip grip shoe option.