Here is an outfit inspired by Dean Winchester from Supernatural that is great for travelling in, it's not that surprising that Dean and Sam do a fair amount of travelling.
This outfit was based of Dean's outfit from the last two episodes of season 9. (He probably wore it in other episodes but I haven't check every single episode.) It is a simple outfit with layers that is great for fall/autumn, you can wear any black shirt underneath the plaid shirt for an extra layer. I decided not add one into the picture because it seem unnecessary as everyone have a black shirt somewhere in their wardrobe (most probably). I added some Supernatural themed jewellery, and that is about it.