Well you shouldn't make him unless it is something he agrees to ... Like you bet him on something and he looses, then he has to wear women's clothes.
But you could do something similar to how my wife did it to me. She got me started by wearing panties and soon she had me wearing panties every day. Soon she started adding to me, getting me to also wear a bra and other items of lingerie ... After a while she threw away the last of my male undies, which I hadn't worn in a long time, leaving me with nothing but sexy lingerie to wear. Then she got me to wear other things, like women's jeans and tops ... And that is how my wife did it.
It is great going out dressed and she loves it too!
Well, if you want to do that out of fun. Then make him loose a bet between y'all!!! LOL!!! Or you could dare him too!!! :-)
If you were trying to get me to women's clothes, you find the job quite easy! Would love a girlfriend to "sort me out" that way.
It would not be proper or healthy for you marriage to attempt to "make" your husband do anything. You might ask him or tell him that it is something you would appreciate him doing for you, but to make him would be wrong. Something of this magnitude should be his decision, not yours. He may feel that his masculinity would be damaged if he did such a thing. If he is not in total agreement, drop it. It is no more proper for you to try to force him against his will into doing something that he finds objectionable than it would be for him to attempt to force you into doing something that you did not want to do. In a loving relationship, force is never used by either party.
Just ask him and find out.