To the casual observer, the Dropbox demo video looked like a normal product demonstration, but we put in about a dozen Easter eggs that were tailored for the Digg audience. References to Tay Zonday and 'Chocolate Rain' and allusions to 'Office Space' and 'XKCD.' It was a tongue-in-cheek nod to that crowd, and it kicked off a chain reaction.
I love a modern suit paired with a polo or cotton T-shirt... and then paired with leather sneakers, or cashmere joggers with a tailored blazer and a sleeveless puffer vest to get the ultimate informal and formal combination.
I like to keep a uniform - wear a blazer, try to keep the same colour pants; very tailored, very fitted but still edgy.
Over the years, I've learned that you can have fun with the fabrics and other elements, but if it's not tailored right, you'll blow it.
A man in a well tailored suit will always shine brighter than a guy in an off-the-rack suit.