For what it's worth, from my experience as a relatively newbie (to riding on the road at least) i've found that shorts were probably the best and most important investment for me. I got some normal lycra (waist) Endura shorts for around 40 notes from Evans and they're just the job. Once I got over the image conscious bit I found lycra more comfortable relative to others I tried - and you can always put a pair of normal shorts over the top if commuting, getting on the train etc. I already had a light and cheap Asender light waterproof jacket which keeps the rain out and the chill off, plus folds up into the pocket, and would recommend at least some sort of waterproof jacket. I prefer layers to a thicker jacket so just a normal micro fleece if really cold, otherwise the normal tops i use for running. And if you've got money to burn don't worry about the all the gear, no idea image - if it inspires you to get up and out, investments worth it if it keeps you fit and healthy.