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Men typically do not wear dresses.

If one does not have the confidence to wear it, he probably shouldn't bother. There is little to gain by doing so.

People, whether male or female should wear clothing that makes them comfortable and which affords practical use for the situation they are entering.

The most I can suggest is stop caring what others think when it comes to your clothing choices. Wear what makes you feel comfortable and provides the level of warmth or number of pockets or whatever else is relevant to your needs.

If the dress by itself is not enough to give confidence, than what is the point in wearing it?

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Q: How can a man get confidence by himself to wear tight dresses in to a store?
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