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@hoefla
is he likely to become a "competitive commuter"? If not, then no need for much specialist stuff. just be sensible about wearing breathable fabrics (merino ftw), trousers that allow the right kind of leg movement and can be tucked into socks or clips. shoes - lightweight low-cut hikers or trail-running trainers are better than normal trainers as they might offer a bit more protection in the rain and wet. I think the most important thing is not being miserable in the winter. decent gloves and a lightweight rain/windproof jacket that can be kept in a bag easily and isn't too much of a sweat-fest, and finally some waterproof over-trousers for really bad conditions, as cheap as possible. I like my Gore Pac lite jacket but I can't seem to find it online now...