Cigar smoking is a classy habit. Contrary to what people who do not smoke think, cigars are not big, expensive versions of cigarettes. There are many differences between them, starting with the fact that you do not smoke cigars the way you smoke cigarettes. In addition, the taste of a cigar and a cigarette are as different as the taste of a pizza and a hamburger. And of course, the price of a cigar is not the same price of a cigarette (although smoking cigarettes is normally more expensive in the long run, due to their much more frequently smoking).
If you want to buy cigars, and are new to the habit, then you should try the cheapest ones at first and buy them by the unit. The cheapest ones cost 2 dollars, so you can practice with them. Of course, the taste will be much different from both a cigarette (if you are used to smoke them) and a really good cigar. The main purpose of this is that you buy cigars that will allow you to practice not only how to smoke a cigar, but how to cut them as well. Because these cigars are cheap, it does not matter if you make mistakes that will cause them to burn unevenly or to come apart. It is probably a good idea when you buy cigars to buy a cigar cutter as well.
Eventually, you will start to buy cigars of better quality. It really comes up to your personal taste and how much money you are willing to spend. I recommend you buy cigars of several different brands and flavors. Over time, you will develop a preference for a type of cigar. Once you find a favorite cigar for you, it is better and cheaper to buy cigars in boxes rather than by the unit. Finally, you will graduate by buying a cigar humidor, which will let you store your cigars and keep them in good condition.
One last recommendation, when you buy cigars, avoid Cuban cigars. You might have heard that they are the best in the world. While it is true that their quality is excellent, and maybe truly the best in the world, they are illegal in the United States. In theory, it is also illegal for an American to buy cigars of Cuban origin in any part of the world. However, no country really enforces the prohibition for Americans to buy cigars of Cuban origin in their territory. Nevertheles, unless you are prepared to make a trip to another country just to buy cigars, avoid them. If you see them in the United States keep yourself out of trouble and do not buy them. Not only they are illegal, but chances are that they are counterfeit.