I like this forum more an more already and it doesn't hurt that many of you are helping to confirm that I'm not alone with some of my tastes. Contrasting collars-IN THE RIGHT SETTING, it looks baller as hell. I own a few light blue/lilac contrast collar shirts and with a dark suit, it stands out a ton in a business atmosphere. With that said, I would never wear one out to a party/club/social gathering Pinstripes-I'd leave them for the office. Again, I love them and half my suits have pinstripes, but they're for business. The only time I'd consider them is with some of the modern brand companies. Ralph Lauren makes a reasonably priced pinstripe suit. The pinstripes are about 1/4" apart and close enough to not give the "investment banker" look. If it were me: I'd wear a black suit, make sure my tailor cuts the hell out of it so it's perfect. I'd do a light colored or white shirt tailored to me and a bright bright tie that stands out. That's more my personality though. If I wanted to stand out even more: Navy suit White checkered patterned dress shirt Bright color dot pattern tie or other tie pattern that contrasts the shirt light brown Brown shoes/belt Just remember, that you can make a $200 suit look better than a $2000 suit with proper tailoring.