Like if you were prepared to spend a substantial amount of $$ (whatever that means to you) on a few items, maybe shoes or a coat, how do you go about shopping for it?

I primarily shop online. For me, I tend to ask friends for recommendations and browse through lists by trusted publications. I look at the product listings for items that interest me, then narrow it down based on available size, personal preferred style, favorable reviews, and ecommerce friendliness (so like, if it's easy to return, track the shipment, and if the site looks trustworthy).

Usually, this process gets me to about three items. Then I agonize over which one is the "perfect one" and then I give up and tell my boyfriend to pick one lol. Sometimes I go with which one he picks, but most of the time after he picks one I realize there was one I was rooting for him to pick. And I go with that.