Boots with shorts.

First post here. I've got a lot of great cues from the sidebar and am in the process of [re]building my wardrobe. One of the key pieces I'm looking for is a pair of all purpose leather boots. I live in Houston tx, where 8 months out of the year I'll be wearing shorts (90+ degrees with 95% humidity.) Versatility is key for me in my wardrobe, and if I'm investing $150 to $300 on a pair of boots, I'd like it to go with more than just pants. I also used the search function for this question and there is a good thread about desert boots with shorts, but I couldn't find much otherwise. The consensus there was Desert boots are difficult to match with shorts.

So, my question is this, what style (if any) of laced boots look good with shorts. I was looking into work boots and Chukkas. Any help would be highly appreciated.