I love your outfit and your 28 cubed challenge. What a fab idea! I'll be following along.
So, I think I figured out what it is I don't like about the pressure to wear belts:
Everyone has something they aren't happy and secure about. That is why dressing in a way that camouflages what you don't like and emphasizes what you DO like is so important. Pear-shaped gals who might be a little more shy about their hips don't get called shorter-top-phobic. Small-busted ladies don't get told that they are plunging-neckline-phobic just because they don't want to draw attention to their bonier chests. So why is it so bad for me to say that I don't want a belt to draw attention to my waist with a belt? My concerns are very real! Every time I go belt shopping, I just end up feeling depressed because the whole experience is spent focusing on a part of me that I don't like. No other body type seems to be pressured to do this with the parts that they don't love, which is why it bugs me. I don't like my waist. I prefer to bypass it and not draw attention to it, and focus on other things instead. I wouldn't tell someone who doesn't like her hips, bust, legs, etc. that they need to put a spotlight on them, which is what a belt does to my thick waist. I realize some people can't live without belts, and that they truly add something to their wardrobe and make some of their tops work, but I don't think that kind of reliance is necessarily a good thing and it certainly isn't a prerequisite to looking stylish. I'm going to try belts anyway next weekend with Angie, but my expectations are pretty low. I do have a stretchy 2" belt, which is supposedly great for me, but I still find it neither flattering nor comfortable (no I'm not posting pics). If that one doesn't work, I am not sure why another style would.
Sorry, SS, for going on this tangent, but your thread reminded me of it. I do think you look good with a belt though! If it was comfy, more power to you.