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A Definitive Guide to Dress Shoes

Posted on the 10 March 2015 by Manofmany @manofmanytastes

Men are simple and like things to be as uncomplicated as possible - especially when it comes to our wardrobe. For example: if we're going to the gym, we grab gym shorts and gym shoes. A trip to the beach means swim trunks and sandals. And anything that isn't a sneaker or a sandal gets classified in the overwhelming category of "dress shoes", right? Wrong. Unfortunately there's more to dress shoes than just labeled as non-athletic, slippery soled shoes you wear to work. There's actually s a science (and a hierarchy) to dress shoes and all dress shoes are not created equal. We help you to understand the differences between an Oxford and a Derby, lace ups and slip-ons and everything in between with this guide to dress shoes.

A Definitive Guide to Dress Shoes

The Oxford (or a Balmoral for our UK bloakes) is probably the most well- known menswear 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.

A Definitive Guide to Dress Shoes

Often confused with the Oxford, the Derby is a close shoe relative. 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 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.

A Definitive Guide to Dress Shoes

In the U.S., Derby's and Bluchers are often used interchangeably to describe the open front lace style, but there is a slight difference. 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.

A Definitive Guide to Dress Shoes

Ahh, the Chelsea Boot. The favorited boot style of rock and roll icons The Beatles and bad ass galaxy soldiers in George Lucas' original Star Wars triology (Yup, stormtroopers have a thing for Chelsea Boots). 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 it's elastic side paneling. Chelsea Boots have rounded toes and are versatile enough to be worn with jeans or a suit.

A Definitive Guide to Dress Shoes

Identified by it's wide heel and slip-on capabilities, the Loafer was inspired by mocassins; the shoe of choice for Native Americans. Like Oxfords, Moccassins come in a variety of lace-less styles (tassel, penny loafer, monk strap, etc.). Regardless of style, in general, Loafers are considered to by the most casual of the "dress shoes". 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. The 3 most popular Brogue shoes are:

A Full Brogue or Brogue:
A wing-tip shoe where the perforations emulate the letter "W" as starting at the centre of the top of the shoe and sweeping around the sides of the shoe.

A Definitive Guide to Dress Shoes

A Half Brogue (Semi Brogue):
A design with some perforations on the edge of the toe cap, but the majority of the design is the decorative perforations in the centre of toe cap of the shoe (medallions).

A Definitive Guide to Dress Shoes

A Quarter Brogue:
This is the same as a Half Brogue, but with instead of the medallions in the toe cap, the Quarter Brogue is plain.

A Definitive Guide to Dress Shoes
A Definitive Guide to Dress Shoes

Chukka's are a Derby styled ankle boot. Typically made from calfskin or suede, Chukka's 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.

A Definitive Guide to Dress Shoes

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 Chukka's have a leather sole. Got it?

A Definitive Guide to Dress Shoes

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...

A Definitive Guide to Dress Shoes

The boat shoe is to 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 shoe laces 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.

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