1. From looking around online, I'd look for a color marked 'brown' or 'oakbark'. If it's a little 'red' it may match better, leather-wise.
http://www.fine-used-sadd.../saddlepics/CWD_35/1.jpg is the link to a saddle I'm getting on trial and will probably buy-and it's also very close to the saddle color I have now. That's a professionally done picture and the lighting is accurate, so if something matches that I would assume it'd work.
2. "Brushing" boots work-they just have to be closed all around (no open front). I'm not a real guru on boot styles out of the jumperworld, so if they go to a tack store and ask for sturdy eventing boots (No fleece/sheepskin, or if there is, easily washable!) that's probably the best way to go.
3. Colors on saddle pads: Dark blue (Royal blue, indigo) or a charcoal grey. Black pads with blue lining, grey lining or blue with grey lining work as well. I'm not big on patterns on the pad itself (I'm assuming pattern as in textile patterns-flames, hearts, ect). Piping or trimming is fine, though.

“There's a lot about discovering who you are and how difficult that is, and it never stops.”
- Libba Bray