By moving on from the philosophical side of things, here are the six items I chose (pardon the wrinkles and poor lighting):
#1: Blue and red plaid button-up blouse. In the land of Oregon, plaid is still hip. And in the land of Grace, plaid hides coffee spots, evidence of dropped kimchee, and overall uncleanliness.
#2: White thermal long-sleeve shirt with gray stripes. Warm, but light enough to not be uncomfortable and suitable for layering. Stripes make thermal shirt look less like long underwear.
#3: Charcoal-gray long-sleeve cardigan. Excellent for layering. Necessary for Portland winter. Long enough to hide unsightly muffin-tops and remnants of holiday overeating.
#4: White tank top. Good for layering and for not unintentionally flashing poor cleavage to innocent bystanders who value their eyesight.
#5: Dark wash skinny jeans. Gap calls the cut "Forever Skinny" but I'm still feeling "Never Skinny" in them. Still, they fit well, aren't susceptible to Plumber's Crack in the back, and are short enough to fit my stubby little legs in.
#6: Black skinny leg pants. They look like a fancier version of leggings, feel wonderful, and stretch in a flattering way. Can be dressed up or down, yet often sit in the back of my closet. I figured this would be a great chance to give them some air time.
I feel that I do have an unfair advantage in this challenge simply because I'm not working right now and spent a good portion of my days in work-out clothes or my pajamas (the two exceptions to the Six Items rule). That being said, I'm gearing up for a busy weekend out and about with friends who'll be visiting from California (hooray!) and a week in Seattle. We shall see how my six items hold out!
And a-WAY we GO!