Hi Elizabeth! The boots in 10 work really well with skinnies/straights rolled up a bit. I've never tried them with bootcuts. With this combination of boots/jeans, I have multiple options for pairings that work well together. Same goes for the tops I packed -- they're the kind of thing that work with skinnies or bootcuts, although of course there are certain pairings that work best. I should have maximum versatility with these pieces. Angie, for once, I"m one step ahead of you -- I have either tried on or worn all the combinations I'm planning for.
The camera bag insert is a new acquisition! I decided to try this solution rather than carry my sling-style camera bag, since my primary purpose on this trip is not photography, and I"m taking very little gear (one body, one lens, lots of memory cards, batteries, and charger -- not even my laptop). I've only tested it out at home, so the trip will be the big test. I think it will work well, based on my brief try-outs -- the insert is easy to use and provides just enough protection for my camera without adding much weight or bulk. I'll post an update after the trip.