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>regular cotton t-shirt
>jeans
>boots (sometimes I carry a pair of converse in my pack, just for the comfy)
As for jackets, it really depends. If it's really cold, I'll either wear a German milsurp coat, or one of those below freezing school bus yellow coats. If it's spring/summer, I'll sometimes just wear a regular cotton hoodie. I've been thinking about getting some sort of windproof, hiking jackets, but I don't really need it.
I also pack one of pick related.