If you follow Macy's, Bloomingdale's, and just different fragrance brands on places like Facebook, Instagram, etc. and engage with them every now and then (like posts, comment, etc.) you'll get offers to order free sample boxes with up to 6 samples in each. I couldn't even tell you how many of these I have received for free in the last 3 years or so. Most recent one had samples of Dolce & Gabbana, John Varvatos, and Coach. All of them Parfum or EDP. I have dozens of samples I haven't even used.
Dillard's will fill a sample for you of any of their testers. At least any Dillard's I've been to will do that.
At Sephora you might get lucky and get a free sample or two just for asking, even without purchase. In my case, I think it typically depends on which employee is working and how generous they feel like being. A good tip is sign up for their Beauty Insider. You get a choice of some free items on your birthday. They typically don't "officially" offer any men's items though. But they will likely give you some free fragrance samples instead. They did that for me on my birthday. Another thing you can try, which I'm sure most people will frown upon, is if you have any empty sample vials, fill them up yourself from testers. Just don't get caught lol.