All perfect praise be to Allaah, The Lord of the worlds. I testify that there is none worthy of worship except Allaah and that Muhammad is His slave and Messenger.
We believe that this matter is determined according to the social customs and common practice of the community that the man lives in. If wearing a headband is peculiar to women, which is often the case in current times, then it is impermissible for the man to wear it because it would constitute imitating women. Ibn ʻAbbaas said, "The Messenger of Allaah cursed the women who imitate men and the men who imitate women." [Al-Bukhari and others]
Al-Munaawi said in the course of his comment on this hadeeth, "Ibn Jareer said, '...and it is prohibited for the man to wear the shoes with thin soles, known as 'hathw', and to walk in them in gatherings and markets.' This type of shoes were commonly worn by women at his time; however, they are not particular to women in the present-day." [Faydh Al-Qadeer]
Allaah knows best.