To Work

Get really dressed up and go to work at your traditionally uber-casual office. Let everyone think it’s for a job interview at a competing firm and hold your nose a wee bit higher, you smug phony. Go to The Capital Grille for lunch and let them call address you as “miss” and put lemon in your water, even though you’re technically only there to redeem a “Free Meal” coupon.

Volunteering with Children

Reach into the far corners of your closet for your Notorious B.I.G. “Juicy” tee since it’s been awhile. Forget that young children are inquisitive little buggers and try to pose so that “I smoke skunk with my peeps” is never legible. Let the other volunteers raise their eyebrows at your adept wardrobe decision.

On the Back of Yvonne’s Scooter

A pencil skirt and wedges is the obvious choice here, no? Lest we forget that this is a pony without a sidesaddle option. Warning:  Your tote bag is crucial, because you’re going to need to cover your lap while you breeze down Hennepin Avenue and hope to god that a.) no one recognizes you, or b.) decides to honk.

To a Dance Night at First Avenue

A cardigan, with a wool miniskirt. Yes, this happened one time, and years later, this category of clothing still remains a struggle, as I am not too keen on traditional “club wear.” Go buy yourself an LBD that you can accessorize the hell out of! 

To a High School Basketball Game

Your class sweatshirt–can I get a whoop whoop for the Class of ‘06?!–and a pair of kitten heels (pin-curled hair optional). Why? Because you’ve got unique style! You wore plastic teardrop clip-on earrings to Kindergarten! You rocked butterfly clips like no one’s business in middle school! And damnit, you were voted “Best Dressed” runner-up senior year! [Preach, Miley.]