The Half-pant

The half-pant (shorts) is, by now, a rope around my neck. I really like it. I really stand for it. It represents a lot to me. In the office, I have sensed it even makes the atmosphere light-weight, collegiate and free-flowing. But the CEO has spoken. So, I spoke with a few people about it:

My Engg counterpart: We are always at each other's neck. We are also great friends. I think he is the only friend I have made in the work environment in the last 20 years. Don't get me wrong. Guy's a rocket. Doesn't mince his words, doesn't shy away from a fight. And I suspect he is quite adept at CYA and politics too. 
Advice: as long as some amount of formality is expected, it's okay. Draw your boundaries and choose your battles. T-shirts and Jeans should be your lowest threshold. 

My wife: It's your Saturn. (Me: What?). Yes, it's Saturn doing this to you. It is making you face all the things that you have escaped from, even looked down upon. Saturn, when he focuses his seven and a half year long gaze at you, does this. 
Advice: Choose your battles. If it is really important to you, fight for it. But is it? What's the dream - lots of people wearing half-pants in the office or large scale financial inclusion of the people. 

My boss, the CPO: ha ha ha ha ha ha ha ha ha ha! At _-_-_-_ , and before that, growing up in a college campus and then another college campus, I have never had to face this question. And then, a deeper conversation ensued:

Me: Boss, this is shitty! I now have to ponder over my wardrobe, thinking what to wear. Earlier, I wouldn't think anything and just grab-wear-go!

Boss: You are wrong. Everyone thinks. It is your self-expression. You express yourself through your clothes as well as through your words. Why do you think you wear flashy socks 
(note: My office nickname is "flashy socks"; I wear multi-colored and different socks on the two feet) 

Me: Because it is fun. And people gift them to me. 

Boss: Fun is your self-expression and people gift them to you because they know you like them.

Me: So, then what? 

Boss: Choose your battles. My 2-cent is Internally, don't give a fuck. Externally, if you think your clothes can make someone feel disrespected, fall-in for the sake of your users and your business. But internally, don't give a fuck. 

... and here I am. Totally not sure how to handle this.