I recommend the 3/4 length series of Icon boots if anyone is looking for a shorter length riding boot that is stylish off the bike but still functional and safe.
http://www.motorcycle-superstore.com...&&Back=226%2c0
At the most you'll just need to add in a extra sole to gain a little bit of cushion. I have the vented 3/4th Field Armor Chukkas and they work well in keeping my feet cool in warm weather. Of course I have just ordered the Accelerant Waterproof Boots for wet/cold weather riding. Both the vented and waterproof versions are stylish, comfortable and they have great ankle support without the full blow motorcycle boot look/feel.