This is a caricature mashup of the classic Tiki Bob mug by Alec Yuill-Thornton with Don the Beachcomber. This Bob has a small mustache, flower behind one ear, and the signature straw hat and khaki shirt. He is also holding a coconut shell cocktail mug with ice, straw, and umbrella.

From TikiLand Trading Company:

"Bob the Beachcomber; born in the early 20th century, was an American adventurer, businessman, and veteran who is known as the 'founding father' of tiki mug culture to many. His face is well known for representing one of the most well known tiki bars in history. Bob eventually was instrumental in helping to expand the art form throughout the United States and beyond, including the Territory of Hawaii, where he eventually settled and called home. This ceramic tiki mug is about 8.25 inches tall, and holds about 25oz!"