My DH is the opposite -- it took his eye a LONG time to adjust to skinnies, both on me and even more so on (some) others. He just doesn't like snug fitting clothing. Tailored, sure. And body con dresses can pass his style filter. But not pants, really. Not ever. He much prefers a fluid fit. Then again, he likes short hair on women, too. He's an outlier. Which suits me just fine.
He also doesn't care to wear snug fits.
I don't comment on his clothes unless he asks my opinion, but he often does ask. I will make suggestions on fit. He is not easy to fit because he has narrow sloping shoulders. He asks me a lot about colours, too, and accepts my verdict without complaint. We tend to agree on colour in general.
He comments all the time and often negatively (at first) on new items I wear. It's not always about figure flattery. It just takes him a long time to adjust to any new look. Typically, if I decide to keep something and wear it happily and with confidence, even if he was a nay-sayer at first he will become an enthusiastic proponent.
The longer I've been on YLF, the more often he will like something right off the bat. It could be that I am choosing better or it could be that his eye is becoming more educated.
Also, I've learned that he is a bit like the forum. It really, really, REALLY helps him to see the item styled as I plan to wear it. If I simply pop it on over whatever I'm wearing he cannot see its potential. He needs to see it in motion, in an outfit, to understand what I like about it.