Well, CCadam, you seem to more "normal" in this situation than many other people.

It's been my experience that clothes ARE an extension of how we feel about ourselves or what we want to put out to the public.
For example: I'm heavy set so when I'm out in public, I check out heavy set women to see what they are wearing; how they choose to or NOT hide their bulges so I'll get an idea of what I would like to try wearing myself.
There are three categories that I've come up with, the slob, the indifferent woman and one that really cares how she presents. The slob either wears something that simply covers her skin. Then the younger woman that wears low rise jeans and a short top with her gut rolls hanging out or she wears tight white pants that show panty lines and every single dimple there. This type could also be classified as "slutty" or "flirty." Then there's the decently dressed woman that hides her bulges with lose yet stylish clothing and cares about whether her purse and shoes match.
The make-up and jewelry also tell a story.

If a "slob" (female) started a conversation with me, say at the mall, I'd give her polite answers, but I wouldn't try to be friendly or continue the conversation.
BUT... I can tell when a woman is dressed poorly because she doesn't have an option! In that instance, I'd be friendly.
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Psalm 119:105 Thy word is a lamp unto my feet, and a light unto my path.