I think I'd give that a pass... The only kilt that cowboy boots might even barely go with would be a denim UK. Once saw pics of a guy wearing those items with a tartan kilt and off-white kilt hose. The result ain't pretty. Much safer with 20-eyelet Docs...

Anyway, hope you have your first day out soon... I have done some prepping of Tacoma for ya already... In fact, was once hit on by a drunk russian guy at a pub northwest of downtown. Talk about a strange experience. If he was a she, I probably wouldn't have minded. But, eh, whatever floated his boat. Needless to say, I was pretty happy to get out of there.

-J