35. Tomacco Farmer Homer
Season 11, Episode 5
Homer strikes upon a million dollar idea by breeding a tomato and tobacco hybrid plant on his childhood farm. And what good is a farmer if he doesn't rock some solid workwear? Homer's worn-in straw hat and roughly hewn suit means he can farm and sell his goods in the same day. This outfit seamlessly blends utilitarian workwear and an aesthetic that gives off an air of trust, which Homer then exploits by getting them addicted to his goods.