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If your kitty is skittish, you may want to make sure to get one where the top can be removed for visits to the vet. That way, you don't have to worry about pulling him out, the vet can lift off the top and do the exam while he sits in the bottom part. Works for my Lickorish who is a very scared kitty around strangers and vets. Also, I would go with a size that would fit the largest size you think he could grow to, then you don't have to get another carrier when he outgrows a small one.

We have a sherpa one (Petmate) for Squeek, it has a front zip door and windows with shades and she comes out the door on her own at the vet. It wasn't actually sold as a carrier but as a portable shelter for pets, but it has a handle on top and works fine as a car carrier, although it would be too large to take on a plane and not suitable for checking in as animal cargo as it is soft sided. We leave it out and open in the house and the kitties like sleeping in it sometimes.
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