The standard menswear selfie.  Oh for shame! — The standard menswear selfie. Oh for shame!

A casual search around the internet reveals most genuine questions regarding menswear pertain to the more rigid aspects of the interest. Questions of propriety are at the top, particularly as concerns weddings. These are the can I wear x with y if the event is at four pm in a non-denominational church sort of queries, to which, more often than not, a good answer won’t help matters anyway. One notch below these are questions of pattern scale or color—a sort of tie, shirt and jacket derby where the obscure is clobbered by the banal. Occasionally one sees an interesting question; I recently ran into: “how does one negotiate boutonnieres and topcoats?” This last one might just as well be the meanderings of an eccentric rather than a genuine concern. (From a practical perspective, I imagine I would transfer the flower from lapel to lapel as needed).

The dearth of consistently good questions in these matters surely stems from the nature of the medium: the internet Q&A forum. On the surface, these outlets encourage rushed answers over thoughtful discourse. It’s unknowable, but I wonder what percentage of how-to-tie-a-bow-tie questions are frantically posted by groomsmen while late for the appointed church time. I was fortunate enough to have an uncle, a retired Royal Navy man, in amongst my groomsmen both admonishing and assisting those few stumped by their bow-ties. But what if no avuncular figure is waiting in the wings, prowling the pews?

Those men who have the experience--that know well the rules and how to flout them--do participate in question-asking of a sort. Digging just a little deeper online, one uncovers member-only forums dedicated to every echelon of dressing, from street-wear to the loftiest bespoke ambitions. The most prolific of these is Styleforum, which is really an evolving and immense library of opinion regarding male dress. I’m not a member, but have read quite a bit of the publicly available content. It can be interesting, self-conscious, combative and revelatory all in a single sitting. Some humble questions are asked, but mostly there is the nervous hedging of uncertainty with blunt, semi-hostile statements of generally agreed-upon principles. The bravest members submit selfies for scrutiny. This strikes me as a very modern way of asking a question.

Image searches can answer those vague questions, like what's the correct facial expression for a gray tweed?  Courtesy of the Harris Tweed Authority Digital Archive — Image searches can answer those vague questions, like what's the correct facial expression for a gray tweed? Courtesy of the Harris Tweed Authority Digital Archive

Of course no one becomes better at anything without asking questions. The right questions, I’ve found, are often silent, and phrased as internal statements or ideas, rather than anything punctuated by a question mark. Contemplating a gray tweed jacket, I wanted to see something similar in action—actually, I just wanted to see recent precedent. An image search is all that was necessary; within a few fractions of a second I had hundreds of examples of the good (at left) and the bad. Very good answers can manifest over time from explicating images. In a similarly broad approach, Adolph loos, architect, essayist, and generally opinionated fellow of the turn of the previous century began many of his short critical pieces with that old standby, the rhetorical question. “Ah, to be well dressed, who does not desire to be well dressed?” (Men’s Fashion, 1898). Better still: “How is Fashion Created?” ((Gentle)Men’s Hats, 1898). But Loos does get rather specific with his answers: “an article of clothing is modern when it is possible to wear it in one’s native cultural environment at a certain occasion in the best society and it does not attract any unwarranted attention.” (Men’s Fashion, 1898). Oh how I wish Loos could see how complicated modernity in dress has become. I imagine he would have many more questions.

Ultimately, the very best resources are those experienced people with whom an hour’s face-to-face conversation is not unusual. I have learned more in an afternoon spent with tailor Chris Despos than a week reading essays or the online debates of the anonymous (but well-attired). My father is another good source, but his wisdom usually comes as a question of his own. At a recent backyard gathering he asked me where he might, these days, find some decent polo shirts. I pointed at my own, asking innocently enough if he wanted something similar. “No” was his flat response. “Shows too much chest.” Point taken, pops.