My friend has come to stay for the weekend, she lives 300 miles from me. We went out last night in a group of six girls, all dressed up and I thought we all looked good!
We had quite a bit to drink and I got chatting to a woman I've seen around but never spoken to before, she was very nice and said innocently 'look at that is that a transvestite' pointing at my friend, 
I didn't want to embarrass her and said no she is lovely but didn't crack on she's my best friend.
Thing is she apparently has a point, I asked another close friend discreetly if she thought this and she said yes! And I'm horrified! OK my friend is a big girl, 5ft 10 and insists on wearing the highest shoes she can find so looks very tall, she has naff 80's hair which she is trying to grow out? She admits its naff!
She had an all black outfit on and black trendy leather jacket and I thought she looked ok? But the more I look at what she wears, I'm debating if it not 'age' appropriate, we are both knocking on the door of 45! 
So WWYD, I hate that people think this of her, so how can I approach it or should I leave well alone?
I've posted before about some people in a pub laughing behind her back a about her hair and I plucked up the courage and told her about it and she agreed, but this is potentially very hurtful? 