Q. I was out last evening to dinner with a rather successful friend of mine who was in town from his international work, and he had a reaction that concerned me about my shoes. We were talking about assessing potential customers in general, and he said that he looks at their shoes first. I said that I had particularly dressed up for dinner and he looked down at my shoes but didn’t comment, which I felt wasn’t a good sign. I have attached a picture of my shoes. What are your thoughts?

A. Well, those shoes are a good bit on the fashion “wild side.” (The picture showed a double buckled monk-strap shoe with added perforations, in a two-toned mix of light brown and black leather.) Surely, both the style and the colors lean strongly to the social side of dressing, and are not for business. Since your friend sounds like he is the judgmental type, it does not seem likely he would admire such a style or he may have been jealous.

While a man’s basic clothing items (suit, shirt, and tie) constitute the main aspects of his attire, his accessories are often the distinctive items that set him apart from the crowd. When I am asked “What are the key indicators that a man knows how to dress with style and taste?” my answer is “His shoes, his watch, and his tie.” Simplicity is essential to good taste in all things, and nowhere more than in shoes. Understated, well-polished, high-quality shoes are well worth the investment.  

I believe that men should wear classic, traditional shoe styles in business situations, and I agree with your friend that shoes send a strong signal about one’s dressing style. This is especially true for business attire. But I am also open to wearing all manner of fun and colorful shoes for casual social occasions. While sneakers or even high-end driving moccasins might not work for certain social occasions, generally, a fine leather loafer is perfect. 

Where I have a problem is when a man confuses appropriate and inappropriate occasions for when and where to wear which type of shoe. Lately, the most common mistake I see is choosing those dark leather shoes with white soles to wear for business or dressy/social occasions. If your dinner actually was a business event rather than a social one, then I can understand his reaction. But if it was  strictly social, without a business element to it, and if the restaurant you were eating in was not some highly-touted, top-of-the-line food temple, then I see nothing wrong with your lighthearted choice.  

Perhaps your friend does not have the same tolerance for casual wear. Also, you mentioned his “international work.” You should know that in Europe, men are much less ready to accept any offbeat deviations from the norm in menswear. An Italian gentleman often may wear well-polished calf skin lace-ups in almost any setting.

Incidentally, not only was I was impressed with your interest in “dressing up” for dinner and paying attention to the fine points of men’s attire, but also to how you processed his reaction to your choice. All too often, men tend to ignore the subtleties of dressing and how the world reacts to them

Please send your men’s dress and grooming questions and comments to  MALE CALL: Lois.Fenton@prodigy.net