Adidas do (or they did last year) long sleeve climawarm tops, with thumb slots and a long neck. They are so good I got 3. Most of the time I don't need a jacket, but I got a very lightweight reflective one if needs be.
I'm still using a nano, which must be at least 6 or 7 years old. About the same size as the current one and fits perfectly into the small pockets on running shorts. Got to replace the headphones however, I use some philips ones with an over-the-ear clip thingy.
I like to run early too, lovely in the summer, but I quit for about 2 and a half months last winter (those magazine shots of happy people running in snow is far from the reality, snow and ice in the dark is not fun. it still hurts.). Was a bit slower when I started back up again, and ran slightly shorter distances but only took a couple of weeks to get back into the swing of things. Really didn't lose much, so I guess you need not worry.