Traveling by yourself, with two small kids, during a style challenge. I won't pat myself on the back, but I won't stop you :) Unfortunately, being a mom does mean that I frequently sacrifice style for function. Not to imply that those are mutually exclusive, but it can be work and sometimes I just don't have the energy to care. I've challenged myself before to pack as light as possible, but this was a little more difficult because I was already restricted to my 30 for 30 items. I really had to think about what I wanted to wear at the airport, since I would be wearing Bauer and would likely have to nurse him on the plane. Not to mention how hot I get trying to get through security without losing anything (luggage-wise or children). I can't even pretend that I won't break a sweat keeping Emberly out of other people's way while I hoist the stroller onto the scan belt, with Bauer strapped to me.
But I did succeed and managed to look pretty decent doing so.