You know, I think you're right about cutting it off gradually -- if you get it cut to about shoulder length, that shouldn't be too much of a shock, and if you like it, you'll probably be excited to cut it even shorter the next time.
Here's why I think no layers can be good -- layered hair, IMHO, tends to look best when it has some body. When I got layers in my hair last time, it looked so awesome when the stylist did it, but when I did it myself, it would look great at first, but by the time I got to work, it was flat and looked stupid. (Isn't that always the case though? I wish I could have my stylist come over every morning! Or, I wish I had long, thick, curly hair!) With it all one length, if your hair is flat and doesn't have tons of body, it still looks sleek and good, and you don't have to fight with it. At least that's my thought. No matter what I ever try with my hair, I always end up going back to all one length, above the shoulders, and that always looks the best. Since it sounds like your hair is about as cooperative as mine, that might work for you, too.
I think shorter hair probably would make you look older, too. Of course, you can always ask your stylist, because they tend to know best.