Packing lessons

This month, I'll be going to an academic conference in Chicago. I'm sure it will be fun, informative, and filled with good academic networking. But none of that is as important to me as what to pack. See, the thing that's difficult for me about packing is not limiting my choices to only a few pieces that will fit in my carry-on; it's the dissonance between the mental image I have of myself -- delivering an academic paper in a nerdy-chic ensemble, strolling happily through the streets of Chicago in some sleek, casual-cool outfit that I picture on the hip urban-dweller of my imagination, and hanging out at a Chicago jazz club in a retro dress, perfect for a noir detective film -- and the practical realities of walking around a cold city, in which I need to move seamlessly between academic appropriateness and casual comfort (and make room in stretchy clothes for all the pizza I plan to eat.) Here's what I ended up with:

1 Pair of Dark skinny jeans -- versatile enough to look casual or professional if need be

1 dark floral dress -- fun, but understated; feminine, but easy to transform with the right jacket

1 Dylan t-shirt -- because I'm presenting on Dylan, so it seemed right

1 grey long-sleeved t -- because it's cold there, and I might need to layer

1 chambray button-up -- the perfect choice for moving from professional to casual in a pinch

1 black blazer -- to make things just a little more "academic" when necessary

1 teal boyfriend cardigan -- for layering and color

1 scarf -- the muted lavender compliments the other colors

1 pair simple black ankle boots -- comfortable, stylish, all-weather appropriate, and just understated enough to pass as professional in this situation.

When I started to pack these into my carry-on bag, look who I found, squeezed into a cosmetics bag:

Perhaps Oscar can be our travel mascot.