Apart from ultra casual shoes - boat shoes etc, I love my RM williams craftsman boots. 2 pairs in comfort craftsman yearling for casual, and 1 pair of signature handmade in french calf for more formal yet non-suit events, all in chestnut colour. For work, allen edmonds monk strap in black cordovan. The RM williams are by far the most comfortable but not dressy enough for work with a suit, hence the allen edmonds. The RMs are so comfortable that I wear them when travelling also, and have no problem with 10 hours and 10 miles a day exploring different cities etc.