It's a good idea to have "big ears" when listening to earlier styles of jazz. Contemporary jazz sounds contemporary; we don't need to make a huge effort to bridge the gap between ourselves and the music. Early styles can sound "dated" or "corny" sometimes. Poor recording quality can also affect our reactions. We have to realize that Louis Armstrong sounded revolutionary in his day: nobody who wasn't from New Orleans had ever heard any music even remotely like that in the 1920s. It was also wholly contemporary with the so-called "jazz age" of the 1920s. It was the equivalent of the Beatles in 1964 or hip hop in the late 80s: something fresh and new.
You don't necessarily have to like something to appreciate it. In other words, there will be things you don't necessarily identify with on a personal level, but you can see how this music was considered fresh, new, innovative for its time.
When I was kid the movie "The Sting" came out with Paul Newman and Robert Redford. The sound track featured "The Entertainer" by Scott Joplin--a ragtime piece. Suddenly every kid who took piano lessons wanted to play that--including me. So in the 1970s there was a revival of the "hip" music from the 1890s.