How do you valuate clothing?

I'm trying to buy a new summer sportcoat and I was thinking about how to valuate clothing. Like for example, I could spend say $500 on STP for an Isaia sportcoat, but for that same amount of money I can buy a Kiton sport coat on ebay or a Canali sport coat in a store. Now Kiton is probably the best of the 3 labels, but the problem then is that you have to choose something from the stock that is available on ebay and you have to buy it sight unseen with very stringent return policies. With the Isaia, you have to choose from the stock that STP has in your size, plus it's sight unseen, but they have a very liberal return policy. With the Canali, it's probably not as quality as the other 2, but since you are buying it in a store you get a larger selection and you get to try it on in the store.

This same valuation method applies on all items. Take shoes as another example. Say I find a pair of C & J handgrades on ebay for $300, but they are a half size too long. On the other hand for the same amount of money I can buy a pair of Allen Edmonds at full retail but with an actual in-store fitting and a selection from any style that I want. Or, I can go to the outlets and buy, say, a SF Tramezza shoe for the same amount of money, but I have to find something in the selection that they have in my size.

It seems like there is always this tug-of-war between selection, service, and price that's kind of hard to figure out. What factors influence your decision on whether to buy a particular item that you are looker for at a retail store, a discounter, or ebay? Or, do you have any other thoughts on this particular subject?

I buy what I like don't sweat the small stuff Odor sometimes the wife won't like the price but this old Trad can take the heat it's not like she isn't wasting more money on Rosenthal dog figurines than I ever could at Brooks or J Press.

my only quibble is that I wouldn't buy a pair of shoes that are a half size too long, especially C&J's for $300...

but otherwise, the concept sort of works. only thing to keep in mind is that while ebay has stringent return policies, you do have the option of 1) selling the item or 2) executing a chargeback, so the risk with the ebay option can be minimized.

I go by function first. what can I really use or what needs to be replaced. Since I am in studio classes around paint and other materials, buying really high end stuff, even on sale is a risk. I value clothes by use and durability. Regardless of name, if it doesn't work and work well i feel ripped off, no matter how prestigous the name. Generally i try to buy better and buy less. (He says as the brown shoes stack up in the closet)

1. Do I need it?
2. How good does it look (includes fit and color)?
3. Quality
4. How often can/do I wear it (i.e. shoes are worn often, while belts are rotated more; this is why I would buy $100 shirts but I might only pay $15 for a belt I wear casually, while paying $100 for a belt that I wear with dressier clothes).