I think that, if you find layers awkward, you shouldn't bother with them. You may have to carry a warmer outer layer as a result, but that will depend on your own internal thermostat. I don't know of any rule that says you must layer. I think part of the answer, too, may depend on conditions where you hike: if you don't need the longjohns during the day, and they're just one more thing to add when you're going to add a jacket and pants, too, then I'd skip them.

Having said that, I find that, here in Ohio/Indiana/Kentucky, between October and December, and between March and May, I like layers. Someone once said that you know you're in Ohio when you go from heat to air conditioning to heat in the same day. It may be cold enough at 8am that I want to start with lightweight longjohns, shorts, and a midweight top. By 10am, I may be down to shorts and a lightweight top - and maybe a T-shirt by 2pm. When I get to camp around 4, the longjohns and midweight top go back on (I pitch my tent, unpack, and get in the tent to change - not a huge nuisance, since I'll need somewhere to sit while I blow up my pad anyhow.) Around supper, I may add my rain jacket (aka windbreaker) and rain pants (which have side zippers for easy on and off.) Around 8pm I want my down vest until bedtime. So, at most I'll have two extra tops, longjohns, and vest riding in my pack. I also find that, at rest stops or lunch, the down vest is too warm, but the midweight wool top (and maybe the jacket) are just right.

However, in February, when daytime temperatures start at 10 and end at 20, I effectively don't bother with layers: I put the longjohns, top, and shorts on at the start of the trip, and they stay on until it's over. The down jacket and pants come out at lunch and in camp. (If I could convince myself I liked hiking in long pants, I wouldn't need the long john/shorts combo.) The rain gear only gets used in the rain or strong wind.

I wouldn't worry about whether I was layering properly - do what keeps you warm.