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As you can see I have a GelaSkin on the back of my iPad 2 and the case is still held securely in place. There is some fraying around the edges of my skin, but I cut it back a bit to fit better into the keyboard case.
Most people will use the Logitech Keyboard Case in landscape orientation, as shown here.
You can use your iPad 2 in portrait orientation as well, the case was designed to support it, and for some applications you may find this works better for you.