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Is it a sin for a man to wear women's clothes? Believers are generally called upon to act with spiritual modesty and decorum so that the world do not have a reason to accuse us of wrong doing. This decorum cuts across our dressing and lifestyle conduct generally. Dressing should also not misrepresent or camouflage our witness for Christ and draw undue and/or negative attention on us. Titus 2:6-10 broadly speaks against any Christian conduct that would open the church community to ridicule and hinder the gospel effort among the Gentiles (non believers). We can borrow the principles in this passage in addressing the issue at hand. The Old Testament laws forbade men from wearing women's clothing and vice versa. Clothing is usually defined by culture where again it was unusual to find garments that were worn across both gender. For believers I would say that it would be inappropriate for one to wear clothes which the prevailing culture reserves for or identifies with the opposite gender. However, with the growing influence of Western liberal cultures across the globe, I recognize that this is a difficult issue for some. Global fashion trends are increasingly narrowing the gap between male/female identity in dressing and the idea of unisex style of dressing or hairstyles is becoming common. It is nowadays normal for women to wear broken jeans and T shirts even in conservative traditional African societies which used to frown at women in trousers or men adorning braided hair. In some communities, men are fast embracing female dressing traits such as braiding of hair, wearing ear rings and studs. Of course we have no single scripture in the New Testament that says "thou shalt not wear a woman's clothes". However, we can identify important principles that should guide us in all prudence when dealing with a question of this nature. The Bible teaches in 1 Corinthians 10:31 - 11:1 "Therefore, whether you eat or drink, or whatever you do, do all to the glory of God. 32 Give no offense, either to the Jews or to the Greeks or to the church of God, 33 just as I also please all men in all things, not seeking my own profit, but the profit of many, that they may be saved" (NKJ). My view concluding view is that if my dressing offends others and goes against the commonly accepted cultural norms, I should do well to avoid that dress in public for the sake of glorifying God. This is one guiding principle of scripture that I consider significant in shaping our moral world view even as we make decisions touching on our Christian conduct. If any act is viewed as immodest in the society or culture we live in, then a believer should refrain from the same, giving regard to the damage that his conduct would bring to the advancement of the gospel. Finally, I believe that it is proper and biblical to seek the leading and conviction and guidance of the Holy Spirit in circumstances where hard and fast rules are not immediately discernible from Scripture. The Bible teaches in Romans 14:21-23 that "It is good neither to eat meat nor drink wine nor do anything by which your brother stumbles or is offended or is made weak. 22 Do you have faith? Have it to yourself before God. Happy is he who does not condemn himself in what he approves. 23 But he who doubts is condemned if he eats, because he does not eat from faith; for whatever is not from faith is sin."
God made them male and female (Genesis 1:27; 5:2; 6:19; 7:16; Matthew 19:4) "The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the LORD thy God." (Deuteronomy 22:5) The Apostle Paul stated in 1 Corinthians 6:9 "Know ye not that the unrighteous shall not inherit the kingdom of God? Be not deceived: neither fornicators, nor idolaters, nor adulterers, nor effeminate, nor abusers of themselves with mankind". Vine's Expository Dictionary of New Testament Words defines Effeminate as: "soft, soft to the touch" (Lat., mollis, Eng., "mollify," "emollient," etc.), is used. (a) of raiment, Mat 11:8 (twice); Luk 7:25; (b) metaphorically, in a bad sense, 1Cr 6:9, "effeminate," not simply of a male who practices forms of lewdness, but persons in general, who are guilty of addiction to sins of the flesh, voluptuous.
The bible clearly says this behaviour is wrong as mentioned in other answers. But why? I believe it is important for Christians to know and understand the spiritual battle behind what is right and wrong in terms of our moral behaviour. If we don't know we're in a battle then we have already lost the war. It is important to understand that the culture of our world is controlled by our spiritual enemy, Satan, and his demonic hordes. They are constantly seeking to change the behaviour of human beings to "corrupt" what God has created as "good". All sin is simply rebellion against the will of God. God's will is expressed in his word. When we obey God's will we honour God. Unbelievers are easily led astray into this corruption. But believers are also being tempted and sucked in to these corrupt practices because we don't know God's standards or because the "desires of our flesh" direct our will instead of the Holy Spirit. Satan, through the culture of our world wants to steal, kill and destroy everything that is true, noble, right, pure, lovely, admirable, excellent or praiseworthy, along with every other positive description of God's creation and the standards of conduct that express his character. So today we have a world culture that is sex crazed and pornified. Everything worldly people say and do (including the way they dress) has a sexual connotation. The culture elevates freedom of expression as the highest value. Whatever two consenting adults want to do in the privacy of their bedroom is acceptable. Then pornography brings many corrupted sexual behaviours into the public realm for anyone who wants to see. This includes adultery, fornication, lesbian, gay, bi-sexual, trans-sexual, queer sexual behaviour (including sex with children and animals). What people wear for clothing then simply communicates the sexual attraction they are interested in pursuing. So Christians can inadvertently lead other people into sin by the way we dress. The bible says that all sexual desire belongs in the marriage bed between a believing husband and wife. Sexual desire, pleasure and fulfilment is an intimate and beautiful expression of love between a Christian couple who have vowed to spend their whole lives together. A true Christian marriage is the foundation of a God honouring human society. Each such marriage is a portrayal of Christ's love for the church. God has a sexual desire protection plan for every man, woman, boy and girl to provide the self-control required for a God honouring life for every believer who wants to seek first the kingdom of God. God has also planned the perfect soul mate for every man and woman who wants to get married and have a family. This is the Good News. The problem we have today is that Christians want to fit in and get along with the culture of our world so we adopt these cultural standards and practices as our own. But God's will is that we take our stand for what we know is right from God's word and transform our culture into the society God intended at creation. Until we know God's word intimately, we cannot discern what cultural practices are acceptable and which ones violate God's standards in his word. Of course, unbelievers have no knowledge or interest in God's standards to enjoy a perfect life, so it is up to us as Christians to convince them by the way we behave - including the way we dress.
I personally feel that all of this transgender, homosexuality and surgically becoming the other sex than what person is born would fall under this same question. I feel that if a person born as a man surgically becomes a woman that would be a man putting on a woman's clothing. "Surgical Clothing" (of the opposite sex) would also be proven wrong (one becoming the other) and does not make the beginning sin (of wanting the same sex) right.
The prior answers are good, but leave out one important aspect. There is the appropriate clothing for the job being done. Many jobs that were exclusively done by men in the past have now become available to women. Safe and appropriate clothing for these activities can be the same for both genders. Otherwise, the clothing distinction would always apply to Christians. For non-believers simply wearing any clothing will become unpopular in the future (Rev 3:18, 15:15) under the beast.
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