Rags Against The Machine

I'm a slim woman in my early 40s -- successful in my field -- and I am always in jeans, a vintage ripped t-shirt, and boots. I mean, ALWAYS. Granted, I have an extremely expensive handbag and perfectly highlighted blonde hair, and I always wear winged eyeliner. My friends say that going "underdressed" like this is disrespectful and inappropriate for (corporate-type) business meetings. Are they right, or is rocking your own thing no matter what a sign of confidence? (P.S. I'd kill myself befor...