MALE CALL: a list of men’s shoes and what to wear with them

Q My husband doesn’t seem to understand that wearing a pair of dress shoes with jeans and a sweater is not dressy for a night out and that wearing work boots with a suit is inappropriate or just plain silly. Can you explain to her that shoes are important, and why they are bad (or about ways to leave your lover!)?

A You are certainly right when you say that shoes are important. They affect the general appearance of a man. In the past, when I’ve been asked which categories of clothing say the most about a man’s taste, my answer has always been “…his tie, his watch, and his shoes.” Although they are the most subtle of the three, the shoes send very clear signals, especially to those who are knowledgeable enough to read their messages.

Perhaps the easiest way to get this across to your husband (and most men) is this:


• SHOE TYPE: Black patent leather “pumps” and plain toe black lace-up shoes

TO WEAR WITH: an outfit with a white tie and a black tie

• SHOE TYPE: Wingtips

TO WEAR WITH: suits, especially dark suits


• SHOE TYPE: Plain toe

PAIR IT WITH: Suits, blazers, smart casuals

• SHOE TYPE: straight toe

PAIR IT WITH: less formal suits, blazers, sports coats

• TYPE OF SHOE: Loafers with tassels and plain

PAIR IT WITH: Khaki suits, blazers, sports jackets


• SHOE TYPE: Suede lace-up shoes (winter)

PAIR IT WITH: Mid-Dress Wool Suits

• SHOE TYPE: White Bucks (Warm Weather)

PAIR IT WITH: Seeksucker suits, khaki suits


• SHOE TYPE: cowboy boots, desert boots (Chukka), moccasins

PAIR IT WITH: Blazers, sports jackets, sweaters


• SHOE TYPE: Platform, sneakers, work boots

PAIR IT WITH: khakis, jeans, shirt sleeves, polo shirts

There is a narrow category of men’s shoes that can go in one of two opposing directions; it can be either elegant or showy and flamboyant, depending on who wears it. In old Fred Astaire movies, he often wears two-tone wingtip dress shoes, called “lookers”. On such a sleek dresser — and on dance floors and ’50s society functions — the look comes across as classic, tasteful, and very special (that would be in the “Dress up laces” category). But what looks good on her probably won’t work as well on most others. If a man who does not have much taste or style wears spectators, the projected image is likely to be loud, garish and far too much. This could fall under a separate category, “Inappropriate”.

No discussion of proper shoes is complete without reference to shoe colors. Well-dressed men usually wear black shoes with blue or gray suits, dark brown shoes with tan suits, and occasional cordovan-colored shoes. These three colors also work with somewhat casual clothes of a similar color. You can veer a little (or a lot) when your clothes are even more casual. For example, bright, light colored loafers, deck shoes and sneakers can be whimsical and fun when paired with khakis, jeans and shorts. Just like onlookers, wearing colorful shoes is another place where the wearer needs a healthy dose of knowledge and confidence to pull off the look.

Please send your questions about men’s dress and grooming to MALE CALL:

[email protected]

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