I've been eyeing the motorcycle commuters for a while now and have noted that most wear tennis/running shoes. Rarely do I see motorcycle specific footwear unless the guy is on a sport bike with full leathers. Here is what I've narrowed down to.
1. Red Wing 970 Boot - admittedly the only HD/biker style item that I appreciate. I like the fact that they function off the bike in regards to appearance however they don't appear to offer much in terms of ankle protection. Most expensive @ $180
2. Icon Supermoto. Kinda fits in with the unique look of the Speed Triple/Triumph bike, not too terrible for walking around off the bike. Seems to offer all the protection I need. Can get for $140.
My Shift jacket does not support zip on leather pants however it appears to have several snap loops that can hook into pants (belt loops maybe). I doubt they would hold while sliding on pavement though. Shift is primarily a dirt bike apparel manufacturer but after trying on several Icon and AlpineStar jackets this one was the nicest in finish and percieved quality. My only gripe is that I ended up with an XL. The large was super tight with the liner (and a t-shirt), almost constricting. However the XL fits really nice with liner but when sitting on the bike tends to rise up into my neck and helmet area. Hoping that once the jacket breaks in (however long that takes) it will not do that so much. Having ridden in it now several times it vents very well and other than the neck crowding I like it alot.