I’m coming up on 3 years riding so I’ve picked up quite a few bits of gear now. My first outfit probably came in around $700 for boots/pants/jacket/gloves/helmet so it wasn’t the best out there. Since then I’ve been adding to it when I had the money and felt the need for something better. I’ve managed to survive the past 2 Seattle winters wearing a mesh jacket with an old cycling GoreTex jacket thrown over the top (with lots of layers). This saved me some money as good jackets can be one of the most expensive items you buy. Probably will break down next winter and buy a dedicated winter jacket as I was surviving and not enjoying the cold weather. May even go down the electric route but that’s even more money.
Nice helmets can be very nice but be aware they don’t necessarily mean better protection. It can mean more plush materials, better paint job etc but it can be the same or worse protection than a $100 helmet. Check out http://sharp.direct.gov.uk/ for a comparison on protective abilities of helmets. Having said all that I LOVE my Arai as it just fits me perfectly. I certainly was not looking to spend $500 on a helmet but once I tried it on there was no going back.
I pretty much wear all my gear all the time. The only concession I make is my 2 mile commute on city streets to work. Then I skip the pants and just wear my jeans but that’s a pretty safe bet. The cyclists are passing me more often than not! The most important thing about gear is to buy stuff that you will actually wear. I have a top of the line external back protector but it just got too tedious strapping it on all the time. I now have a very good protector that fits inside my jacket but I know it’s not as good as the one lying on my closet floor. But in this case convenience won over protective ability.