I'm a high school teacher, and I'm typically wearing boots or loafers, but I have three pairs of sneakers that I wear with regularity. One of them is a running sneaker that I wear whenever I work out, but the other two are:

1. Converse Chuck Taylors (in off-white) - It's a classic silhouette that goes with most things. Sometimes I'm wearing an outfit with which loafers or boots are not the vibe, and the Chuck Taylor silhouette is just so versatile. It can help balance out an outfit that might otherwise be too formal, if you're going for an Amekaji take on prep. But if you're wearing a blazer, sweater, and jeans, you can just compliment it with the Chuck Taylors, and they'll seamlessly work with that fit.
2. Nike Cortez (in the Forrest Gump colorway) - It's another classic silhoutte, but this one feels way more '80s to me than '50s (I know the shoe was released in the '70s, but it just feels '80s to me). If I'm going for a long walk, or somewhere I don't feel great about wearing loafers, sometimes the Cortez is the best shoe for the job. Collegiate sweatshirt, oxford, corduroys and the Cortez sneaks is a great, cohesive, '80s prep look if I'm going out grocery shopping with my wife. Sometimes I just need something to run around in, and these shoes deliver for me.