I love pocket watches, and I have three that I wear quite frequently. Additionally, I have an enxtensive collection of chains and fobs that I also wear on a regular basis. Lots of people admire my watches, chains, and fobs, and have told me that they would like one for themselves but admit that they either can't afford them or they don't know enough about them to go out and buy one. This is a shame, since pocket watches need not be expensive and knowledge of pocket watches need not be extensive.
The first thing to consider is the type of pocket watch you want to wear because they come in three basic styles. A "Single Hunter" style pocket watch has has a protective medal cover over the face that is opened by depressing a botton to allow the wearer to check the time. A "Double Hunter" has a protective cover over the face and a protective cover over the back. This second cover may cover a space meant for a photograph or it may be opened to allow the wearer to watch the gears and gizmos move. The final type is called a "Railroad" style and has no protective cover on either the front or back. Which one is best? It depends on your personal taste. I have several "Single Hunter" styles and one "Railroad" style pocket watch, but that's only because I prefer "Single Hunters."
Another thing that goes along with style is power source, because pocket watches are powered by two different types of power. One type runs on standard watch batteries and the other type is mechanically powered (i.e. it's wound by hand by the owner). Either one works fine, but good-quality mechanical (hand wound) watches are generally more expensive than battery operated watches. Price ranges vary from about $10.00 for basic battery operated watches to many thousands of dollars for mechanical watches handcrafted from precious metals like silver, gold, or platinum).
The next thing to consider is the watch chain. This serves a very practical purpose (securing your watch to your person and extracting it from your pocket), but it is also a peice of jewelry in it's own right so it also serves as an expression of taste and makes a fashion statement. The average guy, however, generally wants it to serve both purposes.
Watch chains come in three basic styles. The first style is a "Single Albert" which is a chani that attaches to the watch at one end (the watch is then carried in a vest pocket) and attaches to a t-bar at the other. The t-bat is then inserted through the botton hole on your vest. It may also have smalled peice of chain dangling from the t-bar side that is used to display a fob. This is my persona favorite since I'm always wearing a vest at work.
The next style is a "Double Albert." This is a "Single Albert" with a second link of chain that goes into the other vest pocket. Generally a small pocket watch, small pair of sissors, or a cigar cutter is attached to the second chain. I like the way these look because they they make a serious power statement, but I don't currently own any because I tend to clip the second half of the chain on things and it just bugs the crap out of me.
The third style, the name of which escapes me, is preferred by men who don't wear vests. It's simply a chain that attaches to the watch at one end and attaches to either a belt or belt loop on the other end. Very simple and very elegant. I have one of these for when I'm wearing a suit without a vest (which is not too often). A variation on this is a simple leather strap that attaches to the watch at one end and a fob at the other. The watch is then placed in the pants pocket and it does not attach to the belt or belt loop. Since I don't own any wrist watches, I have one of these for when I'm just out hacking around in a work shirt and jeans.
The final component is the fob. This is simply a decoration that dangles from the chain, but it can make a very profound statement. I've got bunches of them: semi-precious stones like onyx, old military medals, small pocket knives, part of a Micky Mouse keychain, a pendant that is shaped like a dragon claw and holding a marble.
Your concern should not really be about price, it should be about quality and style (and sentimental value). I have a cheap battery-powered Walmart special ("Single Hunter") that my son saved his allowance for and gave me for Father's Day about three years ago. It's has a gold toned train crossing a bridge with a black lacquered background. I have it attached to a leather strap and use it for my everyday watch. The watch and and strap/fob combined are probably worth $15.00, but it keeps good time and it's my favorite because of it's sentimental value.
On the other end I have a battery operated "Single Hunter" made of silver, engraved with my initials, attached to a sterling silver "Single Albert" chain. The fob is one of my Navy Good Conduct medals. It's worth about $250.00 or so, and it's my dress watch that I wear to church and other formal occassions. In the middle I have a mechanically powered two-toned (silver/gold) "Single Hunter" watch that I wear with either a silver-plated "Single Albert" chain or a "Single Albert" chain made from braided black horse hair with gold-toned fittings. I rotate the chain and fobs depending on what I'm wearing. This is my everyday watch that I wear to work, and it's worth about $100.00.
You can get an attactive watch at just about any department store for as little at $10.00, but the chains usually aren't all that nice. If that's the case, then all you have to do is look-up pocket watch chains on the internet and you'll find nice basic chains that about $10.00. A nice "Single Albert" starts at about $20.00, and a nice "Double Albert" starts at about $30.00. These are usually made of nickle or brass. For a little more you can get silver or gold plated chains. Real silver or gold? Be prepared to pony-up some serious dough, my friend. As for the fob, you can go to a place like Hobby Lobby and find a good looking one made from semi-prescious stones like honey agate or onyx for about $6.00.
That means that a nice pocket watch and simple chain that you can wear with simple trouser and shirt or with a suite will run you about $20.00. If you want a watch and chain to wear with a vest, then you can get a decent watch, "Single Albert," and fob for about $40.00. If you want to make a power-statement, you can get a nice pocket watch, "Double Albert" and fob for about $50.00
Not too shaby for elegance, eh?