06/14/2011 12:31 pm ET | Updated Aug 14, 2011

Purge! Purge! Purge!

This weekend, I enlisted my most stylish friend, Amanda, to help me Stacy & Clinton my closet. My instructions for Amanda were simple: Be ruthless and purge my wardrobe of any outdated, ill-fitting or just plain ugly sartorial sins. The fact was, I owned button-downs I hadn't worn for six years (when I last worked in a business-casual office that demanded something other than yoga pants and Hello Kitty slippers), as well as mini skirts I used to tart around in during my early 20s but would truthfully work better as Swiffer pads today.

Oh, did we purge. We purged like we haven't purged since our sorority days, when breakfast was a Snackwells vanilla crème sandwich cookie, lunch/dinner was peanut butter frozen yogurt topped with Golden Grahams and dessert was four Long Island iced Teas. GONE! was the lilac ribbed sweater with silver neck buckle that I once loved for how it made my small Bs look more like small Cs. GONE! were my brown plaid pants that I used to consider so hip and funky but now look like something my grandpa's gold buddies might rock on the front nine (Morty, however, would never be caught dead in them -- he prefers more of a Mafioso look, complete with black mock turtle neck, black blazer and camel slacks.) GONE! was the black long-sleeved top from Express circa 2003 with black ribbons cross-crossing its open back in a slightly fetishy manner.

Most of the stuff was easy to ditch, particularly my former work attire, which I'll donate to a group that helps homeless women entering the workforce. What proved a bit trickier to bid farewell to, however, was the more body conscious stuff. For example, in a clear plastic box shoved under my bed, we found a hot pink halter top that I wore during my Las Vegas bachelorette party eight years ago. I use the word "top" loosely, because it was basically just a strip of polyester fabric that happened to cover my chest and a few inches of my lower back. Looking back, I can't believe I wore such a revealing piece of trash, but back then, I thought I was the shit, and that shirt was my ironclad evidence.

In the same storage box, we found a similarly flimsy navy blue tank with itty bitty strings for straps. I bought it at Urban Outfitters in 1994, my freshman year of college, and absolutely worshipped the thing. I wore it with tight black pants and without a bra to the bars throughout college; I loved the way it clung to my stomach and showed off my bod... a bod I loathed at the time but looking back, would kill and maim for. (If you don't understand how a college woman could simultaneously hate her body but want to show it off in a skin-tight top, you're probably reading the wrong blog.)

The funny/horrifying thing is, Amanda and I didn't even tackle my "slutty clothes" -- a wicker basket filled with dresses and tops I used to wear in my club girl days. I'm not sure why I'm saving them -- including a black-and-aqua triangle top that basically covered less skin than those clear plastic rings that hold six packs of soda together. Maybe so my nieces can play "Dress Up Promiscuous Girl" when they're seven- and nine-years-old? I suppose I'm holding on to them because our clothes hold powerful memories -- of who we were, of who we thought we were, of who we wanted to be. There was a time when I swore up and down I would never be "the kind of woman" who shops at Ann Taylor Loft; she's now a wardrobe staple. I feel more confident in who I am and no longer have the need to show off all my goods in order to feel sexy or beautiful. And while I'm sure my napkin-sized togs could fetch a pretty penny at the second hand store in Boystown (drag queens know a good pair of black Spandex leggings when they seem one), I've tossed them in the trash. Which may explain why my garbage man is standing outside my garage right now, holding a boom box over his head and serenading me with R. Kelly's Feelin' On Yo Booty.