$100 for a pair of boots is not a lot. I routinely spend $100 on shoes. As a matter of fact my 2 main pair of shoes I wear are both clogs with wedge type heels on them, one brown leather and one black leather and I paid $125 for each of them at Dillard's ON SALE. My K-Swiss tennis shoes (plain white leather) cost $90 plus tax and shipping. I am not a show snob by any means because I would never spend $600 on a pair of Jimmy Choo heels, but I also would never buy a pair of shoes from Payless or Walmart.
Cole Haan makes some nice shoes for men but they are pricey. If your son is picky about his shoes I am sure they make something he will like.
If you want to be shocked, go try to buy him a pair of those black leather boots from the Harley store. You will pay $600 ON SALE. Consider $100 a bargain.
Some things it is ok to be cheap about. If you want to eat generic food or use generic home and bath products, go for it. Save some pennies, but with shoes, I would never try to go CHEAP. You definitely get what you pay for.
I've been having a discussion about this with DS16. Keep in mind that more by circumstance than nature, I have become very cheap. DS is VERY fussy about footwear -- refuses to wear sneakers for anything but gym class (and even then isn't happy about it), and has wide feet, making it difficult to find what he likes. A couple of months ago, his boots (not snow boots, more like black leather sort of maybe biker type boots, which were his everyday shoes) fell apart, and after shopping several places -- and we had to get them that day because he had nothing else -- I spent $70 on a new pair, which made me gag. Now, he's decided that pair is not comfortable for all the walking he does, and asked for a new pair for Christmas. Again, we shopped, and the only pair that fit and that he liked was $100 - at DSW!
Now, I understand in the real world (the world of people who buy things at normal prices, not cheapskate prices), $100 is probably not out of line. But I've only spent that on my footwear once -- a pair of specialized shoes for arthritic feet -- and I can't see spending that kind of money on shoes. But am I being overly cheap? Or is $100 for a good brand that should last quite a while not out of line? (Or am I talking to the wrong audience?)
Look into replacing the sole of his boots. If the body of the boot is still in good condition than, repair the sole and it can continue the life of the boot. My dad does this with his boots.
About the only shoes I pay more than $50 for is DH shoes and DD ballet pointe shoes(specialy shoes). DH is a Marine and he runs alot, between his boots and running shoes, we spend a pretty penny
But we always look for the best price we can find.
Good luck
Three words - price per wear
I think Converse are a case of expensive, name brand shoes that are horrible for your feet. My DD wore a pair as her "good" shoes for years because they were "in" with her friends. DD had foot problems after wearing some cheap Target shoes and ended up seeing a podiatrist, but with her sturdy shoes being Converse, I bet they contributed as well. I wouldn't pay big bucks for shoes like that (we got ours cheap, too). Looking back, I wish I'd not bought them due to all her foot problems.