I saw this really cool pair of boots on my favorite boutique, eBay. The measurement around the top is about an inch larger than my actual leg. Do you think that's likely to cause annoying "boot flap"? It's hard for me to visualize with just the tape measure.

I have yet to try the skinnies+boots combo, but I suppose a gap like that would leave plenty of room for that look, as well as any thick socks in cold weather.