What the F do you bring?

For all intents and purposes, I am going to be on the road until possibly the very end of September. Unfortunately, since this is Canada, it could be 20 degrees in Toronto, snowing in Halifax and the next day everything changes all over again. Now you're just fucking with me.

I currently sit, counting down the days in my Toronto apartment, amongst boxes and suitcases, figuring out what will be going into storage and what will I bring with me. I asked my roommate what she did when she was on tour but she's much more frugal than I am when it comes to clothing:

2 pairs of pants 2 pairs of shoes - one flat & one with heels 1 summer dress that can be dressed up or down 7 tops 1 sweater socks, underwear show clothes

And that's... pretty much it.

She lost me somewhere around 2 pairs of shoes.

For me, I realize that I will need clothes for the gym (more than one outfit if I don't want to be stuck in my stanky sports bra for multiple treks), a business appropriate outfit since I work out of a mobile office and may have meetings, and of course all my roller derby gear and clothing...

Also, my laptop, e-reader, iPhone, receipt scanner, portable charger, and all associated cables that come along with it... (re: mobile office)

But back to clothes: to only bring one of each? How do people manage with two pairs of shoes? HOW DO YOU MAKE IT ALL MATCH?

Joking aside, this is hard for me because even though I use the term #HoboKenny, I always made sure that, no matter what, I never looked like one.

Any other touring performers out there with some tips and tricks?