I’d grab my beloved pair of leather hiking boots instead. I’m a little too far up north for cowboy boots. There’s connotations for sure, but sometimes boots are just boots, and some people really pull them off.

I’m thinking denim jeans and a button-down with a necklace (I’m visualizing a pocket watch necklace for some reason) is a nice look. And then a denim jacket for more layering, but in a different color from the jeans. But not for me, personally.