For dressier days I wear brown Ecco low tops or black Birkenstock shoes (I think they were called "Lawrence") and I always wear those with kilt hose. For more casual or every-day I wear brown Birkenstock hiking boots, black Harley-Davidson jump boots or some shoes I just got from Keen, brown Chukas or black Bronx Mesh. With the boots I wear socks pushed down or rolled unless it's cold and I want more warmth. The H-D boots weren't that comfortable which is why I've replaced them with the Keens. The Birkenstock hikers are about the most comfortable boots I've ever had and the Keens are a pretty close second although they aren't as tough since they're not intended for serious hiking. Just make sure your boots, belt and sporran are the same color for a good look. Like Colin said, check Ham's galleries for the definative look.

Jamie