Originally Posted by 55/Rad
...$200 will buy you a lot if you shop efficiently but the shoes and pedal combination will eat a big part of this. Performance and Nashbar have decent gear on sale at almost all times - shorts, helmets, bags, tools, pumps, computers, bottles, shoes, jackets, jerseys, etc. No need to spend $70 on a Pearl Izumi or like-branded jersey when a generic $35 model will do - and so on. Same for helmets - you can spend $100-$200 or more. But $40/$50 will get you the protection you need from the start...55/Rad
All 100% spot on. If you have a "superstore" type store near you (Performance/Supergo/Nashbar/REI), they'll always have decent stuff on the clearance racks for cheap. Height of cycling fashion? No, but sounds like you want to be a rider vs. poser. Nothing wrong at all with high-end gear, but doesn't sound like it's where you want to be with a $ limit.
The only thing that I might add is that the glasses
are really indispensible. If you have about $20-30 left after some of the higher priority items, look for sales at Performance where they have optically correct glasses with multiple interchangeable lenses. More important if you ride at night, winter or dusk at all because the clear and yellow lenses really save and protect your eyes. Nothing worse than crashing after taking a bug in the eye at speed. Clipless is also a really good thing, but just make sure you practice entry/exit somewhere other than traffic and get REALLY comfortable with this before you take to the streets. Low end SPD and Look have been around awhile and are generally cheap and reliable. Try on as many shoes as you can
regardless of price (so you know what the comfort range is) and spend more of your proportional budget on the shoes than pedals and your feet will thank you. Also practice anticipating slowing/stopping and unclipping well in advance at first. Sudden stops and panic are what make you fall over.