Reyn Spooner Hawaiian Shirt

Key Years: Pre-2000s
Price Range: $35 and up on eBay, depending on rarity of print 

Reyn Spooner pretty much invented the Aloha Shirt. Originally crafted from floral prints on muumuus, their main innovation was "Spooner Kloth." Inspired by the sunfaded duds of surfers, in 1964 the brand simply flipped its printed fabrics inside out when it made the shirts, resulting in a cool washed look. One of the company's most iconic patterns is the "Lahaina Sailor" print, which has popped up in modern collections and collaborations with Stussy.

The old-school brand has a tag with a white background and a circular picture of island life, and is often made in Hawaii, whereas the recent, more modern rebranded duds feature a blue background tag with a simple "reyn spooner" embroidery in white letters.