I dress like this ALL the time, shorts + low boots. I am only 5'4", but I have long legs for my height. So I'm really no expert. I think you could pull it off! Go for it.
I am 5'3" and get compliments whenever I rock this look! Do it!http://cstyledesign.blogspot.com
I love shorts and booties, even more than long boots with skirts. Go for it, besides, booties are great for fall, and definitely look great with jeans too ;)
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