Blue suede Indy boots from Leffot and Alden on the red brick soles. These are super comfortable and seem relatively light compared to the rest of my Indy boots, and the red brick soles are very comfortable, I just don't wear them anymore so time to let them go.
Red brick sole
Black, shell cordovan 6-eyelet Alden chukka from Frans Boone. I've found that the extra eyelets help these lace up a bit tigher around the ankle than the traditional 2-eyelet chukka.
Black shell cordovan
$600 $575 shipped CONUS