New Balance 990 (1982)

The first sneaker to retail for $100 (in 1982 dollars — about $320 today) and the shoe that defined "dad shoe" before that was a compliment. The 990 was made in the USA, cost twice as much as competitors, and sold to runners and professionals who valued function over fashion. Then in the 2010s, fashion swung toward ugly-on-purpose aesthetics, and the 990 suddenly became cool. Aimee Leon Dore, JJJJound, and Teddy Santis collaborations turned New Balance from "your accountant's shoe brand" to the hottest sneaker label in fashion. Steve Jobs wore 991s (the UK-made variant). The 990v6 still retails at $200 and is still made in Maine.