oh!! I do remember the 90s messenger bag craze! I feel it even bled as late into the 2010s?? I remember people where I lived, particularly young to middle-aged men, still wearing crossbody messenger bags through 2015 or so. Further, I remember Joseph Gordon-Levitt wearing one almost exclusively in 500 Days of Summer.
I think it's an excellent look. With the 90s making a strong sartorial comeback, it's time to bring it back, I feel!
Curious and excited to see if you embrace a messenger bag.