Long story short - I have yet to add booties to my shoe wardrobe. Do you all think they will be wearable this coming fall/winter, 2009/2010 (hence the prediction). If so I'm thinking of bighting the bullet and getting a pair.
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Curve: The loveliest distance between two points. ~Mae West
I think since people are trying to get as much use of of things as possible, booties will still be "in." Shoe styles seem to have more staying power than other types of trends (think wedges, flats and even those gladiator sandals from last summer. All are still popular this year.)
And even if they aren't as popular, you can always wear them under pants/jeans during the winter months when it's too cold for other types of shoes. At least that's what I do.
I think if you find a pair that works well with your individual style and your existing wardrobe, you'll be inclined to wear them regardless of which way the wind is blowing next fall. I'm in the same position as you, I just don't see too many I like so I haven't pulled the trigger.
I haven't really taken the time to look, but the fall 09 runway shows are up on style.com, maybe check them out... that's a really good way to predict the fall trends. But that being said, I bought a pair of booties this year and I'm sure I'll at least get a little wear out of them next fall. If you find a pair you love then go for it but I wouldn't get a pair just to say you have some booties :)