You know, with few exceptions, I could never base my wardrobe on what other people think. I'll be brutally honest: I don't think 90% of my friends and family have a clue what they're talking about. I love them dearly, but not everyone is knowledgeable about fashion and not everyone views clothes the same way I do My dad, for example, just buys a size medium and wears it, regardless of how it fits. I see fashion as yet another way of expressing myself and making myself a work of art--dad sees clothes as something to keep him from being naked and cold.
Another male friend of mine thinks "fit" is just a capitalist marketing ploy that I have hopelessly deluded myself into believing. He would be happier seeing me in a sweatsuit and crocs than what I wear now. He views clothing as a political issue. I'm sure he has aesthetic opinions, but he'll never admit it.
Other people in my life care about fashion and clothes but frankly don't know much about them. I have a friend who will buy things because they're soft even if they look ridiculous on her. I know several people who hate skinny jeans on all women all the time. Replace "skinny jeans" with "swing jackets," "wide leg pants," or any other article and cut of clothing and you're bound to find people who feel that way. Personally, nothing is completely off the table for me. There are also people who see things that look good on the rack or on a mannequin and assume that it looks good on them. Also not true.
So in conclusion, unless someone has the same "values" as I do, and unless they are well-dressed and confident, there's no point in asking their opinions.