For a 10 mile commute just wear your normal clothes - if you need padded shorts to ride 10 at a time it's time to HTFU a bit - and a pair of sneakers with clips and straps. Wool is going to be a bit toasty over 85. CO2 inflater or a frame mount hand pump, 15mm wrench, 1 tube, small patch kit, water bottle, lock. Get a Brooks or other leather saddle with saddle bag attachment points and mount a roll up bag under it like others have suggested.

Convenience trumps looks after about one round trip commuting. You're over-thinking it.