Yes. I actually did it all myself. At first it took some time figuring how to work the thing. I got one with 6 different hole punch sizes so you can adjust it to fit the size hole you want. It looks like a pair of pliers with a rotating hole punch mechanism. You have to carefully measure the distance between the holes, mark the exact spot you want to punch, punch through both the front and back sides of the leather to get it to go through cleanly, and then carefully remove the excess fraying inside the hole. I do this by re-punching carefully front and back until the excess leather comes out. I discovered its works best on stiffer leather like my saffiano leather shoulder straps and more expensive leather belts.
This is similar to the one I bought. They start around $6 and go up from there.
http://www.ebay.com/itm/Arrow-6-Siz...603?pt=LH_DefaultDomain_0&hash=item2a51a4ba9b
Here's a picture of my luggage saffiano leather shoulder strap with the additional 2 holes. It's at the newer longest setting.
Thank you so much!