For helmets look around and try on as many as you can. Figure out what size you wear in the major brands you intend to look at, Icon, HJC, Shoei, whatever else you want to look at. Does the helmet fit snug but not to tight? Does it stay in place if you turn your head fast back and forth, up and down (with the chin strap done of course)? ASK THE SALES GUY! Don't let them push you to one helmet or another, but ask them to help you get sized for a helmet. Generally they might know atleast something.
Generally you'll wear the same size throughout that manufacturers line.
Next find what's in your price range. Protection wise you're not going to find a MAJOR difference between brands unless you're paying major $$$$$ for that atmosphere re-entry tested racing helmet. Not to mention when you're on a budget and the helmet takes up $800 of that $1000 you set aside, that's less money for other gear.
Next look through the helmets in your price range, and find the most comfortable. Is the padding comfortable? Does it have any spots that are uncomfortable? Any hot spots where it seems to rub? Would you want to wear it for 2hrs? Does it seem to ventilate well? Is the field of view decent? If you close the visor does it cut out a lot of background noise or does it still sound like it'll be loud when you're doing 70mph down the freeway?
Then when all is figured out, find a paint scheme you like, or do your own! Decals, paint jobs, something to personalize it if you want to.
After that, invest in some good gloves for where you ride. Always go for leather, or kevlar palms. The heavier the better. If it's hot weather go with a textile, mesh, or ventilated leather upper. If it's colder riding, a leather glove with little or no ventilation is fine. Get something comfortable that fits! Too large and it can get hooked up on stuff. Too small and they're rip and wear out faster.
A good jacket WITH ARMOR/PADDING is the best way to go. Sure it'll be bulkier, but when you land on your shoulder or back doing even 10mph it'll feel like someone just nailed you with a baseball bat. Shit sucks, have a messed up shoulder from one of those lil 10mph jobs.
Yet again, leather is going to be the most abrasion resistant...but it's still going to be hot as hell. Textile/mesh is more comfortable and will get the job done. Mesh is great for hot days, but does even less against asphalt. I like Mesh or Textile/Mesh, it breathes well and won't leave you feeling like you're in a sweat box. You can also look into a Leather/Mesh hybrid jackets are also starting to come down in price and are a decent alternative.
As for pants, as wrong as it is most of us just wear a heavy pair of blue jeans at best. It's the wrong answer, but it's more comfortable. Yet again Leather is the best, textile/mesh work, as does the kevlar reinforced denim (Draggin' Jeans for example). Make sure they fit well in a tuck, and that they're not to long as to catch on anything (pegs/shifter/belt for example). If they connect to your jacket in the back, even better.
As for boots, go for comfort and protection. Over the ankle at the least (if you go down in shoes, you can grind the outside of your ankle clear off). I usually just wear my Oakley SI Boots. They're comfy, I have to wear tan boots for work anyways, and they're leather with good ventilation. They may not be the BEST protection (though my issue boots stood up well at 45mph) but they're comfortable and that's what matters in boots to me.
What you buy/don't buy is all up to you, but just keep in mind that skin+pavement=wire brush in open wounds. After it happens once you'll do your part to never let it again.
As for brands, look around in threads here. Alpinestar, Dainese(sp?), Icon, Shoei, and all the other brands people mention a lot tend to be mentioned that much for a reason.