Q I went out to dinner last night with a rather successful friend of mine who was in town from his international job, and he had a reaction that had me worried about my shoes. We were talking about assessing potential customers in general, and he said he looked at their shoes first. I said I had dressed up especially for dinner and he looked down at my shoes but didn’t comment, which I didn’t think was a good sign. I am attaching a photo of my shoes. What are your thoughts?

A Well, these shoes are a bit on the “wild side” of fashion. (The photo showed a double-buckle shoe with additional perforations, in a two-tone mix of tan and black leather.) Admittedly, the styling and colors lean heavily toward the social side of dress, and aren’t for business. . Since your friend seems like a judgmental type, it seems unlikely that he admired such a style…or was jealous.

While a man’s basic clothes (suit, shirt, and tie) make up the main aspects of his attire, his accessories are often the distinctive elements 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 so 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 professional situations, and I agree with your friend that shoes send a strong signal about a person’s style of dress. This is especially true for business clothes. But I’m also open to wearing all kinds of fun, colorful shoes for casual social occasions. While sneakers or even high-end driving loafers may not work for some social occasions, generally a thin leather loafer is fine.

Where I have a problem is when a man confuses appropriate and inappropriate occasions when and where to wear what type of shoe. Lately, the most common mistake I see is choosing these dark leather shoes with white soles to wear for business or dressy/social occasions. If your dinner was actually a business event rather than a social event, then I can understand his reaction. But if it was strictly social, with no commercial element, and if the restaurant you were eating at was not an upscale gourmet temple, then I see nothing wrong with your light choice.

Maybe your friend doesn’t have the same tolerance for casual clothes. Also, you mentioned his “international work”. You should know that in Europe, men are much less ready to accept shifted deviations from the norm in men’s fashion. An Italian gentleman can often wear well-polished calfskin lace-up shoes in almost any setting.

By the way, I was not only impressed with your interest in “dressing up” for dinner and paying attention to the intricacies of male attire, but also how you handled his reaction to your choice. Too often, men tend to ignore the intricacies of dress and how the world reacts to it.

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