OK..
With your jacket I'd go either the Dri rider climate control, the ixon sismic or the rjays tour x
All 3 are mesh jackets with CE armour, a waterproof and a winter liner, prices between 280 and 300. The tour x is a longer jacket, and has the bonus of a 1.5l water bladder. Leather gives you more protection, but hot as hell and not as waterproof as one of those. Textile jackets don't stretch, so make sure you have wiggle room, pull all the liners out and try it on, you don't want it too tight with them in, but if it's too loose without them the wind will use it to beat the crap out of you

Make sure its a snug fit around the waist too.
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helmet, that depends on how big your head is to what brand you buy, if you have a boof head, look at the HJC's, they start at $270 (prob find some cl-14's discounted somewhere)
Smaller heads, the KBC's are very good, if you want a good helmet without spending a lot, the VR1-x at RRP $250 is a good deal, if you want something cheaper the tk-8's at $199 are also very good with lots of ventilation.
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gloves, ideally you'd have two pairs, a summer pair with good protection and a winter waterproof pair. At the moment I'd just buy the summer ones, and if its raining wear latex gloves underneath to keep your hands dry.
When checking fit, make sure you don't have to much excess on your left thumb, too much excess makes indicating a pain. If they fit, the dri rider dri mesh at $70 are a good deal
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Boots
Now this is where you need to spend more. If you're riding your bike in the rain as a commuter, the Gaerne Gsp1 or the forma pro both $299 rrp and waterproof are something to look at. If you won't be riding in the rain, a cheaper boot would suffice, just remember you do get what you pay for. The gsp1 has quite good ankle protection for the price.
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Draggin jeans, very good, but boots are more important. Draggins protects your skin which can pretty much grow back, but boots protect your ankles.
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then hit em up for a discount
There are obviously different things you could buy, these are just suggestions
Remember with helmets, the rule is buy the smallest that DOES NOT hurt.. leave it on, talk to people.. after about 5 min the helmet will either start to hurt or you'll be used to it. Don't buy a helmet that doesn't fit cos even you like the graphics, you'll end up hating it.
Gloves, remember tight, but not restrictive tight.. they will stretch. If something is comfortable when you first put it on it is probably too big
