The longer my husband and I are together, the luckier I feel - honestly. I've never met a more supportive individual and that goes for every part of my life, including shopping.
We moved in together and combined incomes soon after me met and though he was always the major breadwinner (he's older than I am and has a well established career; we met when I was in law school and my additions were pennies) he never made me feel like I couldn't do something because, in the end, he was the one paying for it. He knows I'm not an idiot and know our finances well -- I know what we can afford and he's never said no to me because he doesn't have to. I've never hidden my purchases nor lied about cost -- in fact, I tell him when I buy something and show him as soon as it arrives. Before him, I was as fiercely independent as any of the others who've spoken on that point -- I've always worked and paid for my own things but after living together for a while, I came to the realization that although I wasn't bringing in as much money as he was, I was pulling my own weight in other areas and we both firmly believe that we have an equal partnership regardless of whose name is on the paycheck...
As far as the original question: does he like my shoes (CLs and others)? I just asked and he said he could care less about the shoes -- he likes them because they make me happy and because I look great when we go out and that he's proud that I go home with him. (Awwww!) He's never chosen my shoes for me (nor would I be comfortable with that arrangement) but he does tell me when he likes something.
Also, Choco -- I have to disagree with your theory: DH's mom is not fly -- she's a wonderful woman but I don't think she's ever spent more than $50 on a pair of shoes or any other piece of clothing. My mother was a designer and I grew up around fashion so we come from very different backgrounds. However, he doesn't think I'm frivolous or spoiled or any of those other things and, again, is supportive of the things I choose to spend our discretional income on. Also, as he's not a shopper, I've completed revamped his wardrobe and now he's proud of the way he looks. I remember the first time he put on a
Prada suit -- the jacket alone was $1k but he turned to the mirror and said, "I look like James Bond." Needless to say, we brought it home. A well-fitted wardrobe is key regardless of the price tag. He also makes sure to tell me when women hit on him (he plays it off but I know he secretly enjoys the attention
).
This got long but I just want to end by saying that if you're with someone who makes you feel guilty about making a purchase you worked for, I think you may want to wonder what he will be making you feel guilty about in the future and rethink a few things...