I am a self admitted cowboy clothes Junkie. I have always enjoyed the dressing up aspect of our sport and disagree slightly with the order of acquiring clothing. Like others have said your hat is one of the most important items, in a lot of ways it defines you. You will probably only have one or two hats in your entire wardrobe. Because the price of a good hat is so expensive I would find a cheap hat until you find the perfect one. I would start by figure out who your Alias is, what does do. Cowboys in general wore what ever they had or could find. Some of my best looking outfits don’t match on purpose. Boots are a bit tough too because as some mentioned they have to comfortable all day. If I had to start over I would find a good pair of Lacers or Ropers to start with. Something that will serve me on the range or out on the town. You can get into the more period boots as your develop you caracter. There are so many options for dressing on the cheap but Still looking cowboy. For a very basic outfit a pair of colored jeans and a long sleeve work shirt fits the bill. Go to a couple second hand stores. Look for banded collared shirts that look cowboy. Even a regular collard shirt looks great with the right material. I have found so many usable items at second hand stores you wouldn’t believe it. If you or your wife is handy with a sewing machine its even easier. Check out the vendors both at matches and online. Sometimes there are great deals on close outs and seconds. eBay is an awesome place to look too.
Here is a complete outfit from the good will store. Shirt. $ 3.00. Used green levi’s $ 5.00. Wool sport jacket cut down and accessorized $ 15.00 plus another $ 20.00 in conchos, trim and 4 hours time. Use your imagination there is a lot you can do for very little cash