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1.
1. adj. Having aesthetic or intrinsic charactaristics that bring to mind things that are generally old-fashioned. In the aesthetic sense, this is similar in concept to the term retro, however, "Old-Timey" is usually used to express something slightly more primitive than "retro". Generally, the term "retro" is almost never used to describe things that are aesthetically relative to anything older than about 80 years old, (or generally just the 1920's) and usually represents cutting-edge thought, technology and design of a particular bygone era, usually sometime between 80 and 20 years preceeding the current date.

"Old Timey", on the other hand, is usually used to express someone or something whose general air is more generalized and primitive, and might have a much broader range of nostalgia, usually identifying with things only as recent as fifty years before the current date to two hundred years prior. Anything older than two hundred years old is sort of too old to be considered old-timey.

There is a bit of overlap between Old-Timey and retro, however, there are things that are Old-Timey that are certainly not retro, and vice versa.

A more obvious example might be that of the game Pac-Man. Pac-Man is retro, however, it is not nearly primitive or old enough to be Old-Timey.

The Film Metropolis, although a silent film, and filmed in the 1920's, is also not really Old-Timey either, as it's futuristic art deco look and feel made it stand out in it's day. Though it is from the era of things that could be considered Old-Timey, it rather is more properly described as retro.

Having a handlebar moustache connected to a large, bushy set of sideburns, a hairstyle that was popular for men from around the first quarter of the 19th century into the first decade of the 20th century, is definately old-timey, and much too old-fashioned to be considered retro.

2. adj. or noun. A term applied to music that has a primitave, usually folky sort of sound. Most commonly reffered to Jug Band and Bluegrass music, but also may include Dixieland Jazz, Ragtime, Folk, Klezmer, etc.
1. My uncle bob is very old-timey. He drives a model t ford, smokes a pipe and wears a bow tie. He also participates in Spanish-American War reenactments.

1. The tacky souveneir shop near that roadside Nevada ghost town was built to look like an old saloon. It was very old-timey.

2. I like this barbershop quartet. They are very old-timey.

2. Uncle Jed's Washboard and Jug band play Old-Timey.
by Christopher J Olsen September 10, 2006
 
2.
Of a nature of times past. Rarely replicated in our modern world. Folksy. Often this term is used to describe some thing or process that is not modern. However, it can also mean something that is of uncompromising quality.
Person 1: How come your contractor doesn't use a nailgun to frame? Why does he insist on using his hammer?

Person 2: I guess he's old timey.
by D'Wayne Giles July 10, 2008
 
3.
Of a crappy nature; not refined or developed; poor quality; shoddy
I only got to first base with my Old Timey date last night.
by Studio 004 May 19, 2004