In my experience, I can't wear the same jeans tucked into boots and untucked with other shoes. I need a different pair for each. Even my J Crew Matchsticks aren't skinny enough for boots. I had to get a pair specifically for tucking, and I ended up getting the absolute skinniest skinnies I could find. They look atrocious on me unless I tuck them into boots and I would never wear them by themselves. For regular skinnies, I wear a straighter leg. I do not like tapered or ultra skinny jeans on most women. They look amazing on very slim and rectangular ladies but the exception just proves the rule.
I know what you mean about being scared away from them. I think you just need to try on a whole bunch and see what works. I still haven't found a pair that I really like for myself, and it is my opinion that skinnies really look best on slim, well proportioned women. On everyone else, they only look good with tunics or tucked into boots. I know this isn't the popular opinion here, but my eyes just can't seem to adjust. Every time I have tried on a pair, I feel they make me look top heavy or butt heavy. So all I can say is that if you don't find a pair you love, don't be discouraged. It's really not a look for everyone.
