Letting my guard down

Ah, the problems of being fashion-focused in a small, rural town....

I live in the middle of Horse Country. For all its good points (Wide-open spaces! Fresh air! Beautiful nightly starscapes!) it's not exactly what one would call a fashion mecca. The Horsey Set thinks nothing about pulling off their knee-high riding boots and swanning about town in jodhpurs, sneakers, and disreputable barn coats or fleece jackets. If you've never seen the jodhpurs/sneakers combo, count yourself blessed: it's enough to make this Theorist shudder.

As a result of our town's remarkably casual standards of dress, I'm a lot less on the ball about my appearance for day-to-day trips into town to run errands like picking up mail from the post office or grabbing a few post-blizzard groceries than I would be if I lived in a more fashion-conscious area. I've gotten to be surprisingly OK with running these errands in my gym-going uniform of yoga pants, a fitted tee, and a giant, bright orange L. L. Bean parka that has few fashionable virtues but many practical ones (i.e., it's warm as all get-out and has lots of sizable pockets). To say it's Not Exactly my best look is a mild understatement. Usually, though, that's not a concern: the people I run into in town are dressed similarly, if not even more slubbishly.

Sadly, a close approximation of my normal workout clothes. Unflattering sports bra not pictured.

Unfortunately, yesterday when checking the mail and stocking up on Important Supplies (bourbon and red wine) for the upcoming end-of-the-world caliber snowstorm forecast for today, I ran into not one, but two women sporting absolutely adorable coats. One of them was even wearing a cute denim mini, brightly-colored tights, and cowboy boots. She looked adorable. I looked like a frump.

That's the sort of thing that makes it hard to say "Yeah, I'm a fashion blogger, and I'm trying to make a living as a stylist!"

It's not that I was jealous of her (although I was, a little: did I mention her jacket was really adorable?). It's that I felt I had let both her and myself down. Her, for obviously putting such effort into getting dressed, which I had not reciprocated, and myself, for leaving the house not looking my stylish best - or at least not like a slob. Her cute outfit made my day a little brighter: mine, I'm sure, did not.

I was left feeling a little sad, and not for any conventional reason of inadequacy or jealousy. I wasn't sad that I didn't measure up: I was sad that I hadn't thought to put forth the same effort - it wouldn't have been much - to looking nice instead of slovenly. If I had been on my way to the gym, it would have been different: functional clothing, functional purpose. The gym is the one place where I can let go of the stylistic construction of my body and focus on its sheer formal (form-related, not dressy) significance. I wasn't gymward-bound, though: I went home again before hitting the weight room.

I was sad that I hadn't measured up to my own standards.

I don't think we have an obligation to society to present our best, most polished face to the world every time we leave the house. Down that path lies madness, not to mention putting on mascara to get on the treadmill (if you must, go waterproof). But do we, perhaps, have an obligation to ourselves? Gleeful as I was to see other women walking around my small, unfashionable town looking quite stylish, I came away disappointed because that day, I wasn't one of them.

What are your thoughts? Am I taking myself too seriously? Crossing the line from "image-conscious" into "vain?" Or are my feelings of being caught with my guard down rather reasonable? How much does the prevailing fashion culture of your environment affect you - both how you dress and how you feel about yourself?