I don't know if this little nugget of information is going to make you feel good about 40 or scare the crap out of you but I think you should know... The day you turn 40 that little voice in your head that says, "you probably shouldn't wear that" dies. Yes I said it dies. Dead. Gone. You will no longer care about wearing clothes that are either stylish or appropriate.
For some of us, we resign ourselves to yoga pants. Others retire into fat pants or sweat pants or house dresses. There are mornings when I take the dog out in pajama pants, fuzzy socks and tennis shoes. And I never thought I'd let the public see me in my glasses with my hair all over my head, but 40... I am sure my neighbors talk all kinds of trash about my dog-walking attire. But I don't care. I think this might be the start of an episode of THE PEOPLE OF WALMART but until I show up online in a photo with my butt hanging out of a thong in the candy aisle, I am not going to worry about it.
You shouldn't worry either. You are 40. WEAR WHAT YOU WANT! Maybe we should pick you up one of those cheese bras next time we are in Wisconsin.