If you don't typically spend $200+ on shoes, unfortunately this may be the wrong place to look. I'm truly not trying to be a jerk, but the spend on footwear here is considerably more, most times.
What I can suggest is to look on buy & sell, ebay, and allen edmonds shoe bank. They did just come out with a chelsea boot, although I don't know how weather resistant it will be. However sizing and returns will be next to impossible for these methods.
Blundstones for nasty snow weather will work, and you should be able to find them for $200 ish, lots of coupons floating around for .ca shoe stores.
That is about the extent of it, if you want a finer GYW Chelsea you will need to spend $600-700++
Agreed. But I took him to be saying that he won't buy on-line. Local purchase for at or under $200... I am unable to assist. He could try the Rosen Outlet - their footwear for the most part will be much better than the mall offerings. But $200 there will still be a tough find. Still, I've come across AE boots there for around that price.