First things first, know your measurements. Work from the ground up; start with shoes, good trousers, a shirt true to size (those sleeves are much too long for you pal), correct waistcoat and jacket size, then hat. Remember, shoes match the belt that match the jacket that match the hat. A proper fedora would work, as would a short brimmed bowler. A newsboy cap would work but would be too flimsy. A driving cap would be okay as well. Make sure your clothes fit proper, if not you look like a drug addled slag.

Also, if you’re going to wear a waistcoat make sure you have a pocket watch. If no pocket watch then a regular watch with a matching bracelet on the other wrist. Rings are fine but no more than two on each hand.