This isn’t really a subscription service, but we had to include it nonetheless. Buck Mason is the easiest way to shop for clothes, short of your girlfriend picking things out for you. This company sends you packages filled with staples every guy needs—a gray tee, a black tee, an oxford shirt, jeans, etc. Once you get it, you're given five days to choose what you want to keep, which is the only stuff you'll pay for, and then you return the rest. Perhaps the best part is that everything's American made and classic looking, meaning you won't feel uncomfortable wearing it for years to come.
More info: buckmason.com