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God created humankind in his own image, in the image of God he created them, male and female he created them. — Genesis 1:27 (Net Bible)
A woman must not wear men’s clothing, nor should a man dress up in women’s clothing, for anyone who does this is offensive to the Lord your God. — Deuteronomy 5:5 (Net Bible)
I noticed a few posts lately in Geminispace, discussing the idea of men wearing dresses, usually with a positive recommendation. So this seems like an appropriate moment to weigh in on the subject.
The fundamental issue here is that, in God's created order, men and women are distinct genders, and God wants them kept distinct. Therefore, it is wrong for men to wear women's clothing, and women to wear men's clothing, because this confuses the distinction between the genders.
I have to clarify that, to some extent, the categories of male and female clothing are determined by the popular culture of your nation, region, or ethnic background. Some clothing is inherently gender-specific, such as clothing designed to support your genitalia. But of course pants vs. dresses is not an issue for tribes that only wear robes or loincloths. Likewise, the connotations of styles may change with time. Today in the USA, it is easy for women to wear pants and still appear feminine, as opposed to 200 years ago.
The critical question, for whether or not you are sinning, is whether or not your clothing is blurring the distinction between genders in the place that you live or are visiting. Of course, there are a lot of technical discussions to be had there, but that is the guiding principle. If your clothing is "making a statement" that gender boundaries should be ignored, it is displeasing to the LORD and you should not wear it. (Be sure to find some replacement clothing quickly.)
As to dresses specifically: If you have another garment similar to a dress that you believe can be worn in a masculine manner, you should not refer to it as a dress but by some other name (kilt, toga, whatever). In all my English dictionaries, the word "dress" is defined as a garment with a "skirt" and a "bodice", and is defined as a garment "usually" worn by a woman or girl. In short, the word "dress" has feminine connotations baked into it and similar masculine garments should be referred to by a different name.