Here are my current favorite skinnies, which fit in your price range:
http://www.urbanoutfitters.com.....NS_APPAREL
You can see me wearing them here - first photo on the left in the row of 4:
http://youlookfab.com/2009/11/.....-outfit-5/
These are SUPER skinny - almost like jeggings, except the denim is thicker (and warm for winter). They are very stretchy, but they do not bag out at the knee at all when tucked into boots. They also come in a low rise version. I love the high-rise version, which hits right at my belly button and sucks all the jiggly parts in. These are good if you have a thicker waist too - it's the first time I've ever needed a belt to hold up my jeans!
The reviews say that the black version fades a lot. I have the dark blue, and it has faded somewhat but not too bad (and I've washed them numerous times - I also throw them in the dryer). If you are a rectangle with average or thin calves, these should fit you great. I love them so much, I duplicated.
As for the ankle issue with the boots, it sounds like your boots are too wide for you. Are they supposed to be slouchy boots? Do you have a pic? I have 13 inch calves and I need nothing higher than 13.5 inches in height, and it's VERY difficult to find sleek fitting boots with those dimensions right now. Slouchy, shorter boots I can find, but not sleek, tall ones. Seems everything is designed for a wider calf and taller leg.