Back to a girl's opinion, although one dusty with age. I hate boots with dresses, but if you wanted to wear the combo, they need to both be appropriate for the season. I think that dress is cute cute cute, but too summery for most of the US in October.
Taking in mind my first statement (that I hate dresses with boots), I went looking on the Dillards website to see if there was anything I thought was maybe a bit more appropriate and could possibly be worn with boots, I found this
http://www.dillards.com/product/B.-D...header_juniors. Don't shoot me if you think it's ugly - I was just taking a stab.
And here's a caveat for you. Using the pictures from UGA's rush that is currently going on, it looks like hemlines are mercifully dropping a bit. A lot of what I saw on the Dillards website was seriously short. Now part of that is probably that the models are Amazons, but I'd probably follow the lead of those highly stylish girls at UGA and bring it down an inch or two.