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:
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.