1. Gym Membership
What good is having nice clothes if you're not putting them in the best frame? True, not every guy has a six pack and the muscles of the average member of The Expendables, but you'd be surprised at what regular exercise can do for your style. It promotes better posture, tightens muscles, and in general just makes sure you can keep rocking all that slim-fit gear without fear of having male muffin top. And like having good style, it makes you more confident. What's the harm in that?