You may not like Elminster's design, and he may have old-school wizard aesthetics, but he is not "generic". If you see a pic of Elminster, you know instantly who it is. We don't mix him up with Gandalf. We don't think it's just some random wizard. They don't have to label the picture as "Elminster" so we aren't confused. It's immediately recognizable because he has strong design, even if that design is dated.
The Battle Chasers comic is an example of having many different wizards, all looked dramatically different, and each had unique design. Some looked like nobles, one was a strange, green-headed halfling, and Gnolan was more traditional wizard, but even his design was unique. You could pour through mountains of D&D art references for different ways to make wizards look unique and still look like wizards (and nothing like Gandalf).
Gale could be any random merchant selling shoes. He looks like no one. Why have concept artists? This character could have been auto-generated.
