Ralph Lauren Blue Label corduroy skirt, ruffled plaid shirt, sweater vest, Wolford striped tights, J. Crew shoes
It's no secret that I tend to skew towards the preppy when push comes to shove. Although living in New York has given rise to a new permutation of the style, the whimsy, color, and classic shapes of the preppy are at my core. It's not as though I ever really stood a chance though. My mother always espoused (i.e. bought) classics for me and was a staunch resistor of anything too clunky, cluttered, or trendy (read: no legwarmers, no Reebok pumps, no grungy jeans, etc.). I remember how victorious I felt when I finally finagled a "that looks ok" to a few grungy plaids and cardigans that I so heavily coveted so that I could fit in with my Seattle heroes (because that was only thing that made pre-teen Canadian suburban me so different). In retrospect, however, my mother was probably right that overalls were (and continue to be) a bad decision, and, as a result, her style maxims echo through my current choices whether I want them to or not.
It also doesn't help that when I left home for college, I ended up at a school with a Ralph Lauren and J. Crew flanking the entry gates. Long-storied tradition and practical considerations conspired to prep-ify my wardrobe like it had never been prep-ified before. Grosgrain ribbon was taken to a whole 'nother level. Could I have withstood it? Yes. Did I want to? No. It was just too situational-ly perfect. And it all culminated my last semester senior-year in a glorious blue-and-white gingham formal dress that I will never forget.
Law school in the South didn't do too much to temper the prep indulgences, especially considering that I was down to one J. Crew as my go-to store because of geographical and financial limitations (yes this is before J. Crew started to grow too big for its britches and think it was on par with Barneys, style- and price-wise).
Before I get side-tracked on a diatribe about my recent freshet of disappointment with J. Crew (oh it's coming...soon) -- a warning: preppy can get you in a LOT of sartorial trouble. You can end up frumpy and dumpy without much effort. But if done right, it's a great way for the professional woman to look savvy and at-ease with herself without actually putting much effort in (especially in the winter months). It's also an easy style through which to convey a sense of humor while still being work-appropriate. I know the way I do prep often involves a heavy-dose of irony (and not of the oh-this-is-ugly-so-I'm-going-to-wear-it hipster variety). Just make sure the cuts stay modern and the prints don't get too toddler and you should be safe. And when in doubt, always skew towards nerdy-preppy as opposed to clambake-preppy to stay fashionable.
And if someone ever mistakes you for being on your way to an equestrian or hunting event, take it as a sign of success. :-)