Short answer
No. The Prophet ﷺ cursed the man who dresses like a woman and the woman who dresses like a man, so wearing clothes made for the opposite sex is forbidden in all four schools, even as a joke or costume. A thobe, jubba, kurta or sarong is a men's garment, not a dress. What counts as men's or women's clothing follows local custom.
Imitating the opposite sex in dress, adornment or manner is makruh tahrimi (close to haram). What is particular to each sex is judged by the custom of the place. Unisex clothing that meets the rules of awrah is permitted for both.
The four schools agree on this.
Explanation
Abu Hurayrah reported that the Prophet ﷺ cursed the man who wears women's clothing and the woman who wears men's clothing. Ibn Abbas reported a similar curse on men who imitate women and women who imitate men. A curse marks a serious sin, so the four schools agree that cross-dressing is forbidden.
The thobe is not a dress. People sometimes ask why Muslim men "wear dresses". The thobe, kandura, jubba and long kurta are men's garments, cut and worn as men's clothing across the Muslim world, and the Prophet's favourite garment was the long shirt; see what the Prophet wore. The sarong, lungi or izar is likewise a men's wrap in South and Southeast Asia.
Custom decides. Whether an item is for men or women depends on the culture. Skirts, dresses, blouses, heels and handbags are women's items in most Western settings. A kilt is a men's garment in Scotland, but most kilts end above the knee, which exposes a man's awrah in the Hanafi school. For women, suits and clothes cut for men are not allowed, while loose trousers made for women are fine.
Unisex clothes. T-shirts, hoodies, tracksuits and coats worn by everyone are not imitation. The rules on awrah, tightness and modesty still apply; see tight clothes.
Costumes and jokes. Dressing up as the opposite sex for a play, a party or a prank falls under the same curse. Carrying your wife's bag or borrowing a relative's coat in the cold is not imitation. See also men and makeup.
The evidence
Sunan Abi Dawud 4098
Graded sahih... لعن رسول الله صلى الله عليه وسلم الرجل يلبس لبسة المرأة والمرأة تلبس لبسة الرجل ...
"The Messenger of Allah cursed the man who wears women's clothing and the woman who wears men's clothing."
A direct curse on cross-dressing.
Sahih al-Bukhari 5885
Sahih... لعن رسول الله صلى الله عليه وسلم المتشبهين من الرجال بالنساء والمتشبهات من النساء بالرجال ...
"The Messenger of Allah cursed men who imitate women and women who imitate men."
The wider rule against imitating the opposite sex.
Where the ruling is recorded
- al-Durr al-Mukhtar with Radd al-Muhtar, Kitab al-Hazr wa al-Ibaha, section on clothing. Men and women imitating each other in dress is makruh tahrimi.
- al-Fatawa al-Hindiyya, Kitab al-Karahiyya, chapter on clothing. On what clothing is for men and what is for women.
Checked by our team. For a more accurate answer to your own situation, consult a scholar. Quran translation by Sahih International. Hadith Arabic from the standard editions of the six books and the Muwatta, with gradings as recorded there; the English is our own rendering. Spotted a mistake? Tell us.