I have used a lot of tacks over the years (literally 1,00's) to decorate gear and what was suggested above is pretty much the way to go. Some things to add:
1) Don't worry about getting the pattern too perfect - the originals weren't
2) Old wood workers trick to help keep the wood from splitting - clip the sharp point off.
3) Whether square shank (yes they are available but VERY costly @ $1.00 or more each) or round shank always pre-drill. I too use a Dremel with a slightly smaller bit, but also stop drilling just short of full length of the shank so the tack gets driven into the wood just a bit which helps retention. I also tap them in hard enough so the edge of the head just dents the wood, which also helps with retention and keeps crap from working it's way under the cap.
4) Don't put them where you're cheek will rest, especially if you have a beard. :shocked2: