One thing I firmly believe in is buying quality items. There are stores I won't shop at because it looks as though the dress will fall apart after two washes. If you're going to be buying something classic that you can envision yourself using for a while to come, you should make sure it's something high quality. If it's a pair of boots that will easily last you ten years (and you can envision yourself wearing them for that long) then they're probably worth the money. But only as long as you have it. It's not worth going into debt over a pair of boots (or any piece of clothing). What are you willing to spend money on for quality?