I totally get what you mean,
hair-mess, but unfortunately I am just not a jeans-and-top kind of girl. I feel terribly uncomfortable in jeans, or dressed casually. I love dresses and skirts year-round (especially with tall flat boots in the winter, espadrilles or sandals in the summer), and that is my look, whether on a play-date or running errands. In the summer, it's easier for me to dress "casual", but still if I am wearing pants they are usually white, with a nautical look on top.
I agree that it's the manners and personality that makes the difference and I am pretty approachable and warm

, which (I think!) helps. Fortunately no negative comments, yet.
As far as discussions - and this happened recently speaking with my SIL's friend and her DH - I always stress that the H-items are
commodities, which is a really good way to explain it to men. They understand intrinsic value. They understand resale value. They understand supply and demand. When I check eBay and my DH walks in, I show him how much the items go for, and he knows that many of them are not brand new. It certainly changes the tone of the conversation.