I'm new to road biking and got all the gear in one go, literally everything you would need to start off. Little tool kit, pump, wedge bag, spare inners, carbon shoes (the cheaper ones didn't fit properley and felt awful, and I was getting 40% off...), clipless pedals, helmet, light carbon bike the lot.
I've done more than a hundred miles in less than a week on it. That was out, every evening after work, on the roads with rush hour traffic at times and I didn't get any hassle, apart from one person shouting something at me (I think he said 'crash it!'). I had no chaffing, I didn't have pains associated with anything other than my lack of fitness.
I've been running for years and can train for races very effectively but I haven't been exercising lately. In the winter I wear Saucony lycra leggings because they are comfy and warm. When it came to buying cycling gear I just got what I thought would be most effective, full bib shorts and a jersey and I wear hilly double layer socks for my shoes (I swear by them). I can honestly say that every pound I spent was worth it.
The only thing letting me down is my legs. I went out on it, 5th day in a row of ownership and hit a massive hill about 5 miles into my journey in the countryside back roads, one I hadn't noticed in the car. My legs felt like they were on fire. I was almost at the point of becoming stationary, even on low gears I said I would try to avoid using. It was ridiculous, but at least I can say, without a shadow of a doubt, that the only thing letting my cycling down is me, not my kit. It was my own fault for not taking rest days but when you've got a new toy begging to be used it's hard to resist getting on it for a ride! Time to get fitter and healthier, I felt like a massive knob clipping out and recovering at the side of the road in full lycra, WHITE shoes and posh bike...