Given that Spoo & I have somehow been dragged into this, I have to say that quite honestly, I do find the whole "who is dressed better" ridiculously daft. It's fine when done purely for shits & giggles as in these threads or in the old Friday contests. No-one really took those particularly seriously either. Well I suppose one or two did, but they were just being silly. As a serious exercise I find them rather pointless. We all do things that others will find interesting, and things that others will find banal. I find viewing outfits in that light far more enjoyable than comparing them directly in a fit battle. I've yet to find one person's style that I look at, and think, "yeah that's what I want to look like". Frankly, I hope I never do. It's all an idea here, a nuance there, and trying to pull them together in a way that works for what I do.
(BTW, the answer's Spoo, coz I know he must still have his secret stash of Versace swag ready to bring into play. Now that's what I call a cool cat. )