high-waist slacker

white toque/beanie in California in the summer = check

crisp shades = check
sweet beard = check
comfy classic grey college T = check
boat shoes w/ pants rolled partway up the calf = check
slacks pulled up over belly button w/ shirt tucked in =  wait, what?!!?!!!

I had no idea what hit me as I fumbled to get my phone out of my pocket in time to snap a spy-vs-spy shot of this historical fashion milestone. The gentlemen walking toward the mint plaza café had taken a shocking step toward a whole new realm of normal, artsy, comfortable[?], male fashion--and I had to know more. I had to know if he was a fluky one-off nut or a shining styleprophet. A temporary, statement-making, pop star no one will remember or a bold new trendsetter ushering in a new era of mom-jean slacks pulled up over the belly button. The female version of high-waisted pantalones stormed onto the main stage in recent years....but never before has there been a youthful, hip, male counterpart.

Getting the camera out and ready was just enough time for another coffee house patron to block the photo and prevent the mission from being accomplished. The opportunity passed, the café filled up, and there was no way to get a shot of this incredible ensemble. My cappuccino drinking roommate turned to me--aware that my defeated soul was sliding down the barstool and onto the unforgiving hardwood floor in a sad sagging heap--and said: "why don’t you go ask him? [to take his pic]"

Nope. Can't do it. I can't walk up to someone I don't know and ask if I can take their picture without feeling like a creep, being completely embarrassed, and potentially rejected. So I did what any sane person would do. I thought about it, got up, walked outside, and asked if I could take his picture. And here it is. And here are my two questionnés:
1__No belt, no suspenders, what kind of genie magic is being used to keep these pants up so high?
2__When I declare that I will 'never ever ever' wear my shirt tucked into my pants pulled half-way up over my ribcage--how binding (and/or accurate) will my prediction/oath be?