Dress Shoes

Knowing which dress shoes to wear for the right occasion is just as important as knowing which jacket or tie to wear. Not all dress shoes were created equal. A few basic rules apply to your dress shoes--they should match your belt and they should not clash with your trousers--but really the idea is to wear specific makes for specific occasions. For example, sleeker shoes are more formal. Black shoes are dressier than brown. Slip-ons are less formal than shoes with lacing, and closed lacing is slightly better than open lacing.


The Oxford is the champion of modern dress shoes. If you own only one pair of dress shoes they should be black Oxfords. Often they feature a rounded toe cap design. Men have been wearing Oxfords for formal and business casual occasions  since boots became informal.



Derbies are casual Oxfords. They are better suited for walking and feature open laces, meaning the laces go through two flaps that open at the top and bottom of the tongue.



The wing-tip, with a brogued cap coming to a point at the center of the top curving back and down along the sides, is suit-level in black and business casual in brown man who wears wing-tips more than weekly risks having them integrated into his reputation.



Like Chelseas, dress boots bring an edge to formal footwear. Still, they will not serve you well unless you do frequent business in Alaska, or you are an oil tycoon going attending a dinner that specifically says no cowboy boots.



Loafers and slip ons are huge in America. They are okay for everyday business, and perfect for those who hazard slipping off their shoes under their desk, but not quite formal.



These are shiny black leather slippers with a bow on top. Wear them to the opera if you must. Anywhere else, opera pumps will make you look like something out of a fever dream.

Wearing the wrong type of shoe if the best way to make yourself feel uncomfortable. Likewise, complementing somebody’s shoe is sure to backfire when you call their Oxfords loafers. Dress shoes are full of distinguishing details that tend to get a bit existential. You do not really need to know the difference between a derby shoe and a Blucher, but you should never wear a pair of shoes you cannot name.

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