I commute in smart clothes too, I wear some thick armoured textile over trousers - horrible in hot weather in traffic but worth keeping my legs safe and I have a couple of jackets I choose from depending on weather. - One set of leathers for leisure, and a separate set of textiles to wear over the top of my standard work clothes? - A decent textile jacket, and 2 pairs of textile pants eg. 1x overtrousers/waterproofs and 1x pair for leisure riding? You'll probably want all of the above eventually, textiles are great for winter and leathers summer. But the first option is probably the best to start. If you get good waterproof textiles they'll do you for leisure riding in the winter too. - Just get the leathers and a top box with all my work stuff in I personally wouldn't do it this way, I can't be bothered getting changed when I arrive. - What do I select first - Jacket/pants and then gloves / boots? Or vice versa? Everything.