I wouldn't wear any garish or quirky piece of clothing or accessory. I never did in the past out of instinct. There are only a few exceptions. CONTEXT IS EVERYTHING If I belonged to a club that represents something, I would wear one item with the club's logo or other representative pictures of the activity. And only at the clubs parties or meetings. Nowhere else. I would wear it in a fun date with a woman that I've already mated. That way I can show her my fun side. But, I wouldn't put something quirky on the first dates.
IT MIGHT HELP SOME MEN. If some men are not blessed with good physical qualities; tall, handsome features, etc, they might wear only one piece of accessory that is flashier than usual. Especially if they work in an environment where other men are much better looking than him. It's a competitive world and anything that helps the physically challenged guy is fair play. Again only one piece of accessory. There might be some other situations, where some discreet and quirky stuff might be fun and helpful. I can't think of anything else at this moment. Ah. Lastly, the cuff links with coffe (bean or mug?) is brilliant.