Dressy

The cocktail a woman drinks while she applies makeup and does her hair for a night out, delivered to her bedroom by her gentleman. A proper lady has one before leaving the house.

Husband: "Honey, what would you like for your Dressy tonight?"

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dressy casual

Basically it means casual but not too casual. You need a little spice in the sugar if you know what I mean. That's what dressy means. SO basically, jeans are ok, as long as they're good jeans. And, collared shirt, don't go overboard and wear like a suit. You'll look stupid.

Usher, Kanye West look at the stuff they wear when they're rapping.
They always dress nice, so does P. Diddy.

ex. Kanye West wears a polo and jeans, this is dressy casual.

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Dressy Jessy

Is an online slutty model who will use the pity of every man around to get what she wants and to extort money from.

Tha DRESSY JESSY sent my husband nudes and extorted moneys from him...now we are divorced.