Hmm... I am 5'3.5" (so, on the short-ish side but not very short) and most of the time I am happy with my height, although in the past I have wanted to be taller. I don't find any clothing styles inherently unwearable because of my shortness - to be honest, the fact that I have a short waist is a bigger problem in terms of finding clothing that fits. Yes, I have to hem my jeans, but it's not a big deal and honestly I think premium denim is designed to be hemmed. I don't wear heels over 2" in general, unless they come with a gigantic platform.
I do think that other (non fashion) aspects of life are designed for taller people though, at least in America. For example, I have to raise my desk chair at lab to its highest setting to be comfortable at my desk, and my feet don't always comfortably touch the ground. I can't reach things on the topmost shelves in my kitchen. I find the overhead handholds on the subway really uncomfortable because I have to stretch to reach them. My mom (who is shorter than me) had to have her kitchen counters custom built when they remodeled the kitchen to be shorter than normal so that she could use them more comfortably.
On the other hand, my 5'11" friend is always lamenting that she can never find men tall enough to date! I can honestly say that I have NEVER had that problem.
ETA: When I was visiting Asia (Bangkok and Hong Kong) years ago I felt like a giant, both in terms of height and weight, and I was around the largest size they sold. On the whole, I would much rather feel short than like a giant.