Quick dry underwear? Do you wet yourself constantly?

Why don't you just carry on something with the basics so you don't have to make fanatical posts hedging your bets against your bags being lost.

Unless it is winter and you are going somewhere cold, why would you bring a winter jacket?

Brooks Brother's shirts? The only thing non-iron does for you is ruin the fabric. There are irons in hotel rooms for a reason. Those shirts generally have poor quality fabric and almost always have ugly patterns and colors. Not to mention that they have terrible collars. I always laugh at adults who wear button through collars with a tie.

Wrinkle free pants? How wrinkled do your pants get? Hang them up when you get home. Take 2 minutes to iron them in the morning. Take some pride in your clothes. Regular fabric will always look better than the wrinkle free kind. Perry Ellis? That cheap stuff you get from Macy's?

I get the ideas you have of making things match with everything else, but given that you're checking all of it, why don't you just get a bigger bag and not worry about any of this?