TBF if your constantly "playing" with clothes and don't want to settle into your "house" style your not going to get everything right. While everyones tastes change over time not many men change their looks at such an extreme rate. Personally I don't feel the need to reinvent myself like that. From rugged biker to Cuban playboy to snazzy Italian to the 50s and back in a week isn't for everyone. Though I do enjoy his Instragram account. Its rare that I think he looks bad but his constant image changing seems to have led him to the extreme of a fashionable look, at least over the Pitti weekend, (jackets have gotten longer, pants higher and their getting wider) which as we all know rarely ends well.
I'm sure he'll be in attire that I'll think looks great by the end of the month. You can't be all things to all men all the time.