I have spent HOURS of my life resetting to get the villagers to wear the clothes I want them to wear. I know that's nutty, and I know it's micro-managing...I don't care. So...here's what I do.
I have 4 characters in town, so I either order 4 copies of the same clothes, or just save with the clothes on a bridge. After I save, I pick it up and walk by the villager. Eventually they spot it in your pockets, and they ask for it. If they don't ask on one character, they'll ask on another character. The reason why they might not ask with one character could be that they recently traded with the character or something. Anyway, eventually they'll ask for the item. NOW, sometimes they will try it on. THAT is when you want to save, and do a happy dance. But if they just take it and put it in their pocket, or worse yet put it in their house, then you'll want to reset immediately and try again.
The only other annoying thing, other than having to reset quite a few times sometimes, is that once you get them to change to the new outfit, they will take the old, ugly, unwanted outfit they were wearing, and put it in their house.
I have a solution for that as well, but it also involves resetting. In that case, you wait for them to ask you to give them a piece of furniture. It has to be a small piece of furniture, or when they tell you it's up to you. Then you save, and get the furniture you want to put in their house. Then the resetting starts. First, you want to make sure they are home before you give the furniture to them, that way you'll see right away where they are putting it. If they don't replace the ugly shirt with it....reset.
It's a big headache, but I actually decided on what everyone in town would wear and put in their houses this way. Yes it was insane and took a lot of time and effort, but in a crazy way, that kind of thing is fun for me. If you're only doing it for one villager, one outfit, it's not going to be that insane.
