你要告訴我,你不鼓勵穿运樣裝扮.
If someone discourages you, he causes you to lose your enthusiasm about doing something(=don't want you to wear=not to wear that attire.)
He is determined to discourage you(to wear this attire.)
If you are under order to do something, you have been told not to do it (not to wear the attire) by someone in authority.
If someone in authority gives you an order, he tells you not to do something(=not to wear the attire.)