For my husband, he has lots of hats to wear. His responsibilities as a son, husband, dad and manager at work can get quite overwhelming to the point that he feels imprisoned. I tried to make it sound natural.

This is really good! I think "My husband wears a lot of hats," would sound more natural. Most people use the idiom as "wears a lot of hats" rather than "has a lot of hats to wear." Also "husband" (singular) and "hats" (plural). You have one husband. He wears many hats. Your second sentence is excellent. My only comment is that "imprisoned" is a very strong word. "Imprisoned" implies that he is unhappy and wants to leave. You might mean imprisoned or "trapped," or maybe a gentler word like "confined" or "he is under a lot of pressure."

This is really good! I think the only major change is that you might want to make is: My husband has many hats to wear. (Or, "My husband wears many hats") . A more minor change may be that you could remove "at work" and just say manager. We typically don't think about managers outside the context of work, so "at work" may sound a little wordy. Otherwise, I think these sentences effectively communicate the challenges of balancing many responsibilities. Does your husband have any outlets which ease the struggles of responsibility?

The second sentence sounds great to me! Great job. If it were me, I would write the first sentence this way: My husband wears many different kinds of hats. Hope this helps a bit!