I think it's quite the opposite - he is signaling to his base that he supports their ability not to wear masks while still providing himself cover by saying "we still recommended you wear them - it was a personal choice by the people not to". He's been doing a pretty good job of straddling both lanes the entire time and still is.
Please delete if too political - I don't think there's any commentary on my feelings on Trump either way, more just his strategy.