Starting gear? I mean, you can always choose the starting season. Or is that beside the point? Do you mean that all professions start with spring/summer gear, and it shouldn’t be like that, or that at least the player should be able to choose between winter gear and summer gear? I guess winter gear is equally painful in summer, as summer gear is in winter.
Perhaps all military professions could get an army winter jacket? Too much?
Cotton hat, wool scarf and wool gloves for all professions?
A matchbox to start fires?
I’m thinking that whatever clothes you might include, maybe not choose too durable clothes, so that the player would have to be careful in fights. So you might have a very warm but a fragile piece of clothing.
Is tailor a profession? A tailor might begin with knitting needles, or whatever supplies needed to craft warm clothing.
An EMT could start out with the tin foil “space blanket”.
A bottle of hard liqour for the homeless vagabond types to keep warm. Just for the novelty.
A sleeping bag might be interesting in a winter start scenario where you have only few other clothes - you’d have to stop and warm up every now and then until you find proper clothes.