Wolfgang gives me different shorts all the time. No matter what I’m wearing, fairly certain he’s given me shorts while I was wearing a rain coat &boots, in the rain. He’s a funny guy
I think the villagers pick a random part of the clothes your wearing, then either pick an item that has similar color or style.
In my case earlier, Punchy spotted my brown bomber-style jacket, so he gave me brown tortoise specs. Similar to the first post, Judy spotted the brown short peacoat so she gave the same-colored glasses.
I was wearing a Viking top and one of the villagers said they had matching pants for it. I was hoping that maybe these matching pants would help complete my look, but they didn't. They were white pants and didn't work for me. I was wearing mostly brown and tan, and the white just didn't do it.