09. Conor McGregor — Rolex Sky Dweller, $37,500
Conor McGregor is the celebrity athlete having the nickname “The Notorious.” He is known for his smart suits and his designer sunglasses, and an extensive collection of luxury watches which consists of some truly remarkable horology. Conor McGregor once said in an interview that every time he wins a match, he will add a luxury watch to this collection of watches. Despite having no formal relationship with the company, McGregor has some of the Rolex models in his watch collection. One such watch is Rolex Sky Dweller. Debuted in 2012, the sophisticated watch delivers calibre 9001 (one of the most complicated movements to date), a dual time zone display, and a refined leather strap.