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It really depends on how much you are out. If you are way in the closet then anything goes. If you are out to meet friends then some change of season and change of occasion clothing is good, but if you are out weekly, definitely have different clothes for different occasions; if you don't after a short while you will look like a vagabond with holes in your clothes.

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Q: Should a crossdresser have different clothes for different occasions?
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