Get a Well-Known Brand: Rolex Speedking 6430
If you want a foolproof way to start a collection, go with a classic piece from one of the most well-known luxury watch brands. This 1966 Rolex Speedking 6430 is small in diameter, and its black dial and leather band make it easy to dress up or down. Powell says the Speedking was made famous during World War II when the German watchmaker Hans Wilsdorf allowed all British POWs to pick out a Rolex and pay for it later, taking each man upon their word. Many chose this model because it was one of the brand's least expensive options.
[From $1,000, crownandcaliber.com]