Q. Later this month I’m finally meeting in person a woman I’ve only corresponded with online. We’ve seen each other on Zoom and know the reality of what we look like, age, etc. She is my height and in many of her posts I see her wearing heels that I think are 2-3″. Would it be appropriate, wrong, psychologically weak to show up in cowboy boots to keep us generally at the same vertical?
A. For the most part I’d say that would be fine. Your question really brings up three topics: Dressing with another person in mind, the appropriateness of cowboy boots, and shoes as a means of height adjustment in general. Let’s look at those in that order.
I’ve written a good deal recently (and over the years) about men needing to ask about the dress code. This is important for a wedding, a social event, or in a work setting. It certainly can also be true on a date or even on many simple nights out. There is a commercial running that is certainly of current day men dressing: it shows a first date with a well-dressed woman and a man embarrassed by his wrinkled, stretched out T-shirt. The premise is that a crisp T would be acceptable . . . now, that’s a stretch. A date need not be formal attire, but some level of attention and consideration is always appreciated.
In any setting where you are not 100% sure how the person you’re meeting intends to dress, it makes sense to discuss it. This can be as simple as “Should we dress up?” or “I’m thinking this is a casual bar; am I right?” This will put each of you at ease and shows thinking, caring, and smarts. In this case, you might say “I have a nice pair of boots, do you think they are appropriate for ____?”
Now, about boots.
Generally, when considering whether to wear boots, men should keep in mind that they may not be appropriate for the occasion. No matter what you may read on some blog saying that Western boots can go anywhere, they are actually a casual accessory and they do not go with everything or everywhere. If you are in the Southwest and your boots are Southwestern without too extreme a level of showiness for the situation, the answer is almost definitely “yes.” An inappropriate amount might be boots made of two-toned ostrich, with a silver tip, etc. If you are in a city where you can imagine that a good number of the other men might be wearing similar boots (or similar ones but of lower quality), again, it seems fine. On the other hand, if you cannot imagine another man possibly dressed with similar boots within a 10-mile radius, if you won’t/haven’t discussed it with your date, and if she seems rather conventional in her dress, then you should definitely think twice. And, if she is “dressing up” for your date, you may well want to skip the boots.
Beyond boots, there are few other options for a man to adjust his height. Shorter men have good reason to love cowboy boots where the heel can add anywhere from an inch to more than two inches of height. A thick insole can add even more. Realistically, a change of 2-2.5″ is very unlikely to go unnoticed. For a shorter man who is known as such, boots can be a giveaway that you are trying to hide your height, particularly if they have design features that makes them especially eye-catching; as such they are probably not a good idea. In order not to call extra attention to your height or to any effort on your part to appear taller, your boots should be rather plain and not overly memorable.
Incidentally, there also are instances where a date may want you to have as low a heel as possible. One of my sons is 6′ and lives in the Southwest with a wife who is under 5′; she doesn’t seem to care about his wearing boots – partially because the difference would be hard to close, but it is important for him to know her opinion. And that brings us to the psychology of it all, which is not my field, but clothing choice certainly involves a lot of it. If you show up in higher-heeled footwear, and, like you, she has seen pictures of you dressed as you usually do (without those heels), she is likely to catch on why you have chosen that footwear. This may not be a great way to approach a first meeting. But, most of all, once again, I suggest communication. If you have discussed your clothing in advance, you can move on to other topics, and not start with any anxiety about that decision–a first date presents enough things to consider (and be concerned about).
Please send your men’s dress and grooming questions and comments to MALE CALL: Lois.Fenton@prodigy.net
