I loved reading all the above posts. It made me look at the "question" with different eyes. I have since found that I don't mind seeing younger people wearing clumpy boots with light clothing. Would I follow suit? No, sorry, I would feel like a bag lady, but I certainly wouldn't "condemn" another old Biddy doing so.
Fashintern: You are absolutely right! I actually read your resume as your post amused me so much and guess what? We share the same birthday!! :O)