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Know Your Dress Shoes

by Kevin Yapjoco
31 Jul 2017 | 2:10 PM

There's more to dress shoes than just lace ups. They come in different styles that range from formal to casual and everything in between. A man doesn't need a pair of each kind of shoe; most will do with the first two identified here. But as you expand your wardrobe it's good to know what's out there and where they are appropriate.

1. Oxford

The Oxford is the classic and formal English shoe. It has two distinguishing features: closed lacing, where the flaps are stitched together at the bottom; and it has a curved stitching from the bottom of the lace section to the welt of the shoe. Most Oxford shoes these days have toe caps but it isn't a defining characteristic. It also happens to be James Bond's shoe of choice.

When to wear them: Black tie events and weddings.


2. Derby

The Derby is a more casual shoe than the Oxford. It has an open lacing unlike its formal brother where the flaps are not stitched at the bottom to the vamp. As a casual shoe they are far more versatile and can be worn dressed up or down, with a suit or with chinos.

When to wear them: At the office.

3. Monk

The monk strap is a style of shoe without lacing. Instead it is replaced by a buckle and strap and usually comes in either single or double straps. It's not exactly a popular shoe style but enthusiasts have made it more common in recent times. In the formality scale it sits between the Oxford and the Derby but is as versatile as the latter making them very appealing to many.

When to wear them: When you want to wear something different.


4. Loafer

The loafer started out as an informal slip-on but has been continuously refined over time into a full-fledged dress shoe. Many prefer to wear it because it is comfortable and gives an air of relaxed elegance. A popular variation is called the "Penny Loafer," which got its name from when children used to place a penny in the characteristic front slot of their loafers that could be used for an emergency phone call home.

When to wear them: Casual Fridays.


5. Brogues

Brogues are the classic business shoe, adapted from its use in working outdoors. Unlike other shoe types they are not defined by their closure style. Instead they are defined by an upper that is made with multiple pieces of leather and has decorative perforations, a medallion and serrated edges. Brogues come in four flavors: full, semi, quarter and the long wing.

When to wear them:  At the office.



The full brogue, also known as the wingtip, has a toe cap with a medallion and "wings" or serrated edges that run on both sides of the front and ends before the heel.



A semi brogue has a toe cap with a medallion and serrated edges.



A quarter brogue has a toe cap with serrated edges but no medallion.


Long Wing

The long wing is a type of derby shoe that has a toe cap with a medallion and "wings" that extend to the back of the shoe.

Photo Credits: J.Crew, Wildsmith, Crockett and Jones.