Here is another look not every bachelor can pull off. The ascot. You probably want to be at least thirty five, although there is no legal age of consent on this one. The not so humble ascot sends a message: you are a man of wealth and taste (or at least taste) and you are not necessarily related to Thurston Howell III.
When a tie is not binding, when you want to put a little more anti-sprezzatura in an open shirt, consider the ascot. You might look like an aging retro playboy, and your problem with that is?
I have worn one many times at many different occasions, and all I have received are compliments. It helps if you have a little gray at the temples, and a very nice white shirt and blue blazer to frame the ascot.
You will either shun it or love it. If you love it, why not explore the possibilities on amazon. Many styles to choose from, so click on the image above and start necking.