This week on Twitter I shared a picture of a sweater that drew some nice compliments when I wore it to work. I think the fact that it's a really nice sweater (It is!) combined with getting it out early in the sweater season (when, presumably, we're more likely to dole out such compliments) probably contributed to the accolades. Whatever the reason(s), I'll certainly take the kind words.
Now I bring up the sweater because it launched a larger dialogue (mostly in my head; though my wife and certain colleagues were also privy to the deliberations) regarding how one transitions from the clothes of one's youth to the clothes of middle-age. On the face of it, this concern seems trivial, or maybe vain (likely both). I suspect there might be something larger at work though. Our appearance is, in many cases, the first impression we make. How we tend to that impression then influences how people respond to us. That much is obvious. Our appearance though is also a reflection of how we feel about ourselves and how we'd like others to perceive us.
The conflict arises when our 40, 44, or 47 year old selves still feel like our 26, 28, 34 year old selves. "It can't be time for khaki ball caps, Dockers, and Lands End gear!" you think, but then admit you do feel a little silly in the clothes that were once staples of your wardrobe. If you grew up allied with any of the various youth subcultures (metal, punk, indie, rap, goth, stoner, grunge, slacker, beat, hip-hop, skate, etc.) this issue is even more pronounced. You've invested heavily in a particular identity and now, in your advanced years, it's turned on you! Rather than helping you look cool, these fashion accouterments make you look...well...kind of sad.
While I expect this transition is one that most individuals will likely navigate on their own, I'm taking mine to the people. You see, I own a number of articles of clothing that I might very well be too old for (see examples above). As a reality check, I'm going to enlist you, gentle follower, to help me decide. Henceforth, before I go out in a shirt, shoes or jacket that might cross into the realm of "sad middle-aged dude trying to look young" I'm going to vet it online and ask for your feedback.
I haven't ironed out (Ha!) all the details yet, but I'm thinking the format will be a tumblr blog, possibly called, "Does This Shirt Make Me Look Ridiculous?". Stay tuned.