I, too, have "wrestled" with these things. After many many months of thinking (too) hard about head coverings, I came to the conclusion that they are a good thing, mostly because they are a physical practice in humility, which is something I struggle with. I understand the flip side perspective, though, where the head covering instead could become a source of pride. But for me, the head covering issue became a thorn in my side simply because I found I was more concerned w/ what people thought than, well, what God thought (haha it's true tho). So that's when I decided to get over my self-consciousness and just "try" it, to see what the spiritual benefits might be. Now, for me, there was actually a very practical benefit that I feel is tied to their original use, which is that I have long, thick hair that goes all over the place, and even in a pony-tail, when I do a bow the pony-tail would flop over my shoulder and into my face. Not to mention my silly habit of swishing my bangs to the side - I have some fidgeting problems, which manifest into me playing w/ my hair a lot. By covering my head and using the covering to get the hair outta my way, I can participate in all the physical aspects of our worship (sign of cross, bows, etc) without distraction. Beyond this, another reason I have stuck with it is because my patron is the Theotokos, and as my avatar suggests, I want nothing more than to emulate her (even though I do a bad job at it most of the time), and as everyone always says, her head is always covered in icons. Anyway, these are a few of the reasons why I continue to cover my head.
An important thing to remember is, everyone is at the divine services to pay attention to their relationship with God, not the people around them. The fact that we all face forward, including the clergy, is a testament to this, IMO.
As for modest dress, I personally usually go for ankle-length skirts or dresses (which I usually then wear a shirt over the top to make it more like a "skirt" since many of my dresses are spaghetti strap), precisely for the reason you said: bows and prostrations, etc. This hasn't been a huge problem for me, since my personal every-day style in spring and summer consists of broom-skirts ("peasant skirts" as some call 'em), so I have many. On top, I have cultivated a daunting collection of solid color cotton t-shirts, in many many colors
The only advice I can give for finding skirts that fit you and are the length you want is to try thrift stores, since those are the only places the broom-skirt style is found these days (unless you count Urban Outfitters, but I can't afford that lol). Good luck on your search for clothes!