As graduation day quickly approaches, I have begun the Herculean task of sorting and stuffing my life into boxes. Sifting through the contents of my desk drawers has been easy; I have no need for a mediocre SOSC paper or a paper bracelet from Summer Breeze. It’s simple to pitch things into the recycling bin and move on.

Working my way through my closet has been a bigger challenge. As I’m tossing things into piles—keep, donate, store, can’t believe I ever bought this—I realize that I’m not just organizing blouses and boots: I’m trying to begin imagining my new life.

For months, I’ve known that I need to start creating a professional work wardrobe and have been methodically adding more mature, structured pieces to my collection of whimsical T-shirts and flouncy skirts. I’m working on ways to make a gray pleated Calvin Klein dress (scored on sale at Macy’s) more funky with a woven leather belt and bright wedge sandals. Thanks to some recent additions to my wardrobe, I’m ready to hit the ground running—or, more likely, to be teetering on my high heels—in my new job. What I hadn’t realized was that the clothing transformation would extend to my life outside the office.

My favorite Web site, Jezebel.com, has a new feature I can’t get enough of. The installments of “Dress Code,” by blogger Sadie Stein, feature collages of gotta-have-’em clothes for events like date night and different kinds of workplace environments. The most recent edition focused on building a post-college wardrobe, which caught me by surprise. For the first time, I realized that I’m in my 20s, and I’m a soon-to-be college grad. I guess I should start dressing like one.

Combing through my closet, I realized that I had a particular idea of what a post-college lady looks like. I just have a hard time seeing myself in that vision, and envisioning that person in some of my clothes. Does an emerging professional woman wear hoodies on the weekend? Probably not, especially not shrunken ones with her high-school team mascot emblazoned on the front. My frumpy weekend wear no longer seems appropriate for a person who is closer to womanhood than girlhood. I’m trading in my frayed jeans for dark wash denim in trouser cuts (Old Navy has some for $14.99), and my tank tops for blouses with interesting patterns and prints (J. Crew has some excellent options).

For the first few moves during my college career, I held onto things for sentimental value. After lugging boxes of oversized, sweat-stained dance company T-shirts up four flights of stairs last summer, I have renounced sentimentality in the name of simplifying the moving process. Instead of hanging on to articles of clothing, I can scrapbook my memories with photographs, and save both space and sanity, as well as spare myself some serious arm fatigue.

But what to do with the piles of clothes that are in good shape, but too tight, too casual, or too high school to come with me to New York? If you’ve got prom dresses stuck in the back of your closet, donate them to The Glass Slipper Project (glassslipperproject.org), which donates dresses to underprivileged girls. Other options include the Salvation Army or homeless shelters. You could also sell or swap your clothes to Buffalo Exchange in Wicker Park (buffaloexchange.com), and use the proceeds to buy some new threads.

I’ve accepted the fact that I have to purge my closet in order to make room for the woman I’m starting to become. Since getting rid of stuff I don’t need, it’s easier to see myself in her shoes.