Q My nephew is a senior in high school. I'd like to give him a Christmas gift that would help him transition into adulthood and would appreciate your thoughts on two choices. I was thinking of giving him a set of cuff links or perhaps a messenger bag that could also double as a lap top carrier. Do either of these seem better than the other?
A I like both of your ideas for your nephew, but I prefer the cuff links. The reason is not just the obvious one -- that my interest lies with all things wearable -- but because my guess is that he will probably buy himself a carrying bag (and might have a preference for a particular style and shape). My strong feeling has always been that the very best gift is something that a person would really enjoy owning, but that he is not likely to buy for himself. The reason could be the expense, that he thinks of it as too luxurious, or even too frivolous. Whatever the reason that he might not buy it, he still would enjoy owning it. Cuff links fit that category.
If these are his first pair of cuff links, you might want to look for something simple and classic like a plain silver bar. If you know that he already has a few sets, then you might consider the more offbeat silk knots that come in various colors. At the higher end are gold designs; less flashy types are brushed silver or pewter; a fun set might be something along the lines of tiny dogs or bumblebees in colored enamel. These are good because they help tone down the dressiness of cuff links. Of course, cuff links are useless without the appropriate shirts; if you do not know whether he has any, you might want to consider his other standard button-cuff shirts, or also buy him a shirt to wear with the links.
The best French cuff shirts are all-cotton; they can run from $20 on sale in a department store to many hundreds for top quality business wear ... probably not for your nephew. Of course, starting with a solid white broadcloth shirt, your other choices include a blue pinpoint Oxford cloth or a blue-and-white stripe. While making a purchase that takes a man in a new direction can be thoughtful and fun, it is probably wise to consider how dressy his other traditional cuff shirts are, to see what he likes to wear.
Though I mentioned that the messenger bag could risk being a style he doesn't prefer, that doesn't mean it is out of the question. If you know him well and believe you can sense what he enjoys, it could be a fine choice as well. A nice leather or top-quality bag can help, as you said, "transition" him from a grade school knapsack to a professional briefcase (or at least a high-end satchel). However, unlike cuff links, these are a very visible part of his look and, thus, they mean you may be affecting his appearance every day. Choose carefully.
If you or other readers are looking for gift ideas for other men, I can suggest a few clothing-related gifts that fit the "would like to own, but won't buy oneself" category. Some of these are more appropriate for a variety of older men rather than someone in his late teens. They vary for those in different fields of work and come in different price ranges. You might consider: a cashmere sweater, a silk scarf, an alligator wallet, a fine money clip or key ring, a special necktie, a tie clasp, shirt studs for formal wear, a genuine badger shaving brush, a quality umbrella, a high-end ballpoint pen, a set of unique metal or enamel blazer buttons, a cozy terry or flannel plaid robe, a leather Dopp kit, a bomber jacket, or an upscale polo shirt with something special about the design.
Keep a few personal notes in mind: If a man has Mediterranean coloring and doesn't wear camel-colored clothes, don't buy him accessories in earth colors. Try to think outside the box, but within what matters to him. Knowing his interests or hobbies helps, such as cooking, golf, gardening, reading, fishing, etc. It's better to give one well-thought-out gift than a few that are less connected to him.
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