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I have heard this term and being new, just what is dressing in drab?

It is dressing as a male or boy mode.

I call it drudge clothes.

There is a long history of drag and drab in the performing arts.

Dressed as girl
Dressed as boy

OK. I dress as a male or boy.

Do I wear lipstick, earrings, jewelry, ladies shoes,etc.

I am still confused.

You don't have to use those terms to describe yourself. :-)

When you see others use the word "drab" it just means they're referring to being dressed as a male rather than en femme.

In the evenings at home I'm often in a male robe, but female wedge sandals; I wouldn't call that drag or drab, just "comfortable".

I think that en drab or en femme is mostly an expression of how you want to be categorized by total strangers. If you dress ambiguously, some will notice, and some will not. Personally, I think you should dress however you wish. It should be a constitutional right, though I don't see that in our lifetimes, or at least not in mine.

Wearing jewelry is less and less thought of as a girl thing.

Ladies shoes are still a sign.

What's worse, reasonable heel heights for a girl like me are still way too hard to find!

We have to accept responsibility for the consequences of dressing however we please, though I think there has been a slight improvement in how the average person sees us, thanks in part to Hollywood having slowly discovered our demographic segment.