My dad's a Harley guy, keeps telling me to get one - but idk I really love the "standard" look and I'm not a fan of the bobtail or chopper or anything like that (though I did raise my bars which did wonders for my comfort on long rides).

Indians are cool, I would also look at Triumphs and Royal Enfields for the classic Euro/American bike look, but basically every brand has a "modern classic" line right now since that became trendy about ten years ago. I would avoid getting an actual classic until you're really experienced at maintenance, lmao.