A bit of background first. I work as a product designer in a large company, leading a team there. Given this is mostly IT, the dress code doesn't really exist to begin with. Bosses high up can be barefoot or in Bermuda shorts, for one. T-shirts are common. And Dilbert, when it comes to engineers. Sweaters and hoodies when it comes to my peers. The office have a few that dress in suits and seem to pay attention to what they wear, but end up looking like charicatures that are out of their rightful place.
Another aspect is my role and how the clothes should reflect that - stand out some, but not become a joke. Express creativity. I've done my share of street wear and splashes of color, but now when I close my 40's I feel a bit more... continental perhaps. I like my brogue oxfords/derbys, trench coats and black architect turtlenecks, but that is a little one sided. White shirts I've tried feel ok, but might need a bit more of splash of something.
Ideas would be welcomed!