James is the only male Silent Hill protagonist with blond hair. He has a men's classic medium-short hairstyle with longer (side-)bangs, parting of the hair slightly to his left.

He wears a black t-shirt with wide neckline underneath a taupe gray-mixed polo shirt.
The most memorable piece of his outfit is his jacket though, which comes closest to an M-65 olive drab field jacket. Check local or online Army Navy stores; this type of jacket is not too difficult to find and almost all Army Navy stores either carry them or can order them for you.
Still there are a few things that need to be modified:
on James' jacket the right chest pocket is missing; in it's place you will find two patches, reading EastEnD and fronTier. Right above his left chest pocket is something that kind of looks like a round button pin that lost the front part with the picture. Next to this James has a patch with the flag of the United States of America.
On both his arms, right underneath the shoulder, he wears yellow red patches. Make sure you attach them to your jacket the correct way: on both arms the red line on the patch is pointing towards James' back.

James also wears a pair of basic dark blue jeans and black harness boots. He does not wear any kind of jewelry, not even his wedding ring.

Nice accessories for the cosplay would be the steel pipe, the board with nails or a printed out photo of Mary.
The flashlight also is optional, since James does not always have it either.