I'm awfully late here and have little to add, but wow, such an interesting conversation.
I remember a similar discussion earlier this year when Aida mentioned that her hubs does not care for tucked tops on women, considering them masculine. I think it was with trousers, perhaps, not skirts.
Meredith, I'm a bit perplexed that your husband doesn't like those dresses. I wonder why? They don't even have a similar cut. So it can't be the shape of them.
Claire, I have been wondering about your harem pants and why we haven't seen them yet in a WIW (or I missed it)! Now I know the reason.
Rae, I have no solution. I like the boots you already have. But if your husband really dislikes them then I do think it makes sense to replace them, especially if you wear them typically with him. As for the perfect replacement pair, I'm no help at all.
My husband usually likes the stuff I buy, at least if it has YLF approval. Occasionally he will reject something (white jeans) but then he often comes round, if I keep it, to loving it (white jeans again). It's very convenient for me, of course!!