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Tuesday, September 1st, 2015 10:03 pm
I hate shopping for clothes. I'm terrible at it, and it takes forever, and it is miserable. I have stories.[1] This is no doubt part of the reason that I'm getting close to the point where my entire wardrobe needs replacing.

And that strikes me as an opportunity. Part of my problem, I'm sure, is that I've never had even a slightly concrete sense of a personal style: what sort of look might be a good fit for me, and what sorts of clothes could get me there? I realized a few years back that I'd actually appreciate having some rudimentary answers to those questions, and I have a decent guess that it would make shopping less horrible.

The challenge, of course, is that there's presumably quite a bit of effort involved in figuring this stuff out from very nearly complete ignorance, and I've got plenty of higher priorities for ways to spend my time. (That's not even including the fact that trying to contemplate this stuff hits all my usual "oh god I'm shopping" buttons.)

So this is my question, or my plea: are there shortcuts? Can I find some algorithm or assistant who (perhaps for some not too painful investment of my time and money) could help me skip over most of the dreaded "personal style 101" tedium and get quickly to a halfway decent wardrobe? (In a perfect world, I'd be able to emerge from the process with at least a rudimentary idea of what made it decent. Enough so that I could have some confidence in my ability to shop for new clothes later, and maybe even use that as a starting point to learn more as time and interest permitted.) I'd welcome any suggestions, general or specific. Note, incidentally, that I live in a rather small town nearly an hour's drive from the nearest decent-sized city, and that my work schedule these days is roughly 9-5 (plus lumps of evening class prep and grading).

[1] Well, really just one, but it makes the point. A few years ago, I was trying to buy a few shirts at a local department store. I spent entirely too long wandering back and forth through the store figuring out what the options were and which ones I liked and whether the ones that fit came in other colors. How long, you ask? Long enough that about 3/4 of the way through, a security guard walked by to ask why I'd been hanging around for so long. "I just really hate shopping," I said, and I guess I was convincing enough that he left me alone.


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