Q I'm a single man in my early 70s. My new lady friend has been telling me about a gentleman she knows who unwittingly dresses in what she calls "a gangster look." The only thing she refers to is his wrap-around sunglasses. Can you explain what other clothes might make a man look like a gangster? I certainly want to avoid that. We older men without wives need help!
A I'm not really sure that wrap-around sunglasses constitute "a gangster look"; generally speaking, they are either viewed as bicyclists' wear, slightly out-of-date ("Matrix" style), or an older man's look (the large ones that fit over glasses). I do agree that the mobster look is certainly an image to be avoided -- at any age. And I commend you for paying attention to such a remark and taking her seriously. Too many men do not pick up on such helpful signals.
The primary image that comes to my mind when I think of typical Hollywood (if not real world) gangsters is the combination of a very dark shirt (black or navy blue) with a sharply contrasting (white) necktie. While the reverse of this look is an elegant, gentlemanly combination (a white shirt with a navy blue or a black necktie), this is what I always refer to as "a Nathan Detroit look," (referring to the gambler character in the play, "Guys and Dolls"). Subtler versions of this were worn by Regis Philbin in his "Who Wants to be a Millionaire?" days ... and perhaps the concept of stealing money might have been in the premise of the show.
A so-called, full gangster suit is usually pinstriped with stripes that are too-bold or too widely-spaced. Another look that fits this characterization is one that used to be acceptable, but is now not only dated but rather widely considered unacceptable; it's a trench coat in dark leather ("Matrix" again). Other elements that also had their eras of being in-style might include too much shoulder padding, a flower in a lapel, or an oversize bright pocket square (although a subtle one, correctly folded, is still totally appropriate).
Accessories are the area where it is easy to go wrong. While small, tasteful cuff links are a timeless and handsome choice, oversize links have always been an element of low-class dressing. What is "oversize"? Well, dime-size is fine, but as big as a nickel is probably pushing it. In fact any flashy jewelry is to be avoided. In upper-class circles, a gentleman does not wear any glittery, clear gems, such as diamonds, sapphires, emeralds, etc. But formal men's cuff links and studs can include a discreet sprinkling of small, opaque, semi-precious stones, such as onyx, mother-of-pearl or lapis lazuli. This rule also applies to rings. In fact, wearing any ring that is not a wedding ring, even a college ring or a signet ring, is questionable. But never, under any circumstances, wear a ring on your pinky finger. Also, in the highly questionable jewelry category are men's bracelets and neck chains of any size.
I do have one final suggestion. Given that she brought this up, you might gently ask if there is any piece of clothing that you wear that is her "gangster" style. While you and I may not agree that it is, it will be clear that it is something she prefers you do not wear.
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