I would go for dark colored suits with bright accents - a navy or midnight blue suit with orange or lavender pinstripes paired with a paisley shirt and some tan colored shoes and matching belt, for example, conveys power, but also expressiveness. No sunglasses at night - that is just way too clichÃ©d. If you want accent jewelry, and you want it to be flamboyant, try a Chrome Hearts bracelet. I like the idea of the navy suit with a blue gingham shirt and orange tie. To spice up this look, you might want to pair it with a really interesting belt. Maybe get him into a proper jewelers and have a special buckle made, or look for one in a vintage shop. I like the idea of a celtic belt - a little different from the prevailing western belts that I think are really starting to bet played out. And of course, if he is a gallery owner, he needs a proper black suit. I wear mine with everything, from white shirts to silk paisley ones - depends on his personality. If he is really innately supercool (which I suspect he is not) maybe he could pull off the all black look. You know, a black Dior or Helmut Lang suit with a black shirt and a black tie - maybe even a leather tie. Okay, you've gotta be really sure of yourself, and have just the right look, to pull this off. I tried once - bad, very bad, idea. If he really has money, I light the look of a Lucien Pellat-Finet knit under a black suit. The blue suit/orange tie thing is pretty standard, but do you think this guy can really pull this off the flamboyant stuff though? Of course, I'm not a gallery owner. But if I were, I'd probably try all sorts of crazy crap. Way, way more crazy than these suggestions - but then again, I probably wouldn't need a consultant. Or maybe I'd need one to stop me from expressing my inner Elton John/David Bowie/Mick Jagger.