Here is my two cents:
I like a classy style with a touch of trendy. I am older and still like to keep up a little. I may wear a trendy pair of jeans that fit well and have no skin showing and pair it with a classic one color sweater or shirt. Keep it simple.
I ask my daughter how they look. She will always tell me the truth
I do not ask hubby cause he will usually say "That looks fine!"