Check the closeout sections of the online and brick and mortar stores to find the best deals. Generally these will be last year's fashions or other discontinued items, but the discounts can be pretty big.
I haven't visited a Cycle Gear in person for a while, but that seems the way to get clearance items. So far it's sometimes even items on clearance which aren't labeled! A knowledgeable associate will know. Looking online, I basically don't buy anything because the deals aren't as good. I hear on this thread that Cycle Gear has a clearance section online, but as a huge man, aka average, but labeled huge to motorcycle gear (5'10" and 195 lbs with too much muscle for any armor until I found XXL by Fox (mechanic by trade)).
They really do let the ladies look good in their armor.
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There are some things that can be used several ways. I have a mesh padded jacket I wear all year. During rain I can put in the waterproof liner. During cold I can wear thick clothes underneath. During summer I just use with a t-shirt underneath.
My riding pants are ordinary jeans but with several extra layers of jean material sewn into the extended knee area.
My boots were more expensive, but I wanted some that fit well and could be worn all day without hurting. They have been rubbed/sprayed with waterproofing.
Be sure to get ear plugs. Some new silicone plugs have different cores that can be switched to give more or less wind noise reduction.
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Lots of great advice Ronk, may I ask where you found the extra layered jeans? I like my mechanic's pants as they're way tougher than jeans, but other than knee pads I'm still looking. (sorry if this is off the ladies topic, but wherever he found it maybe they have ladies cut stuff too!

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I use old tan boots which are "Army" issue and they work great, but they suck up rain like they they're trying to save the cow they used to be attached too. Would water-proofing them work? Where can I get some? Recommendations? Would they stay breathable or should I get another set of boots for when it could rain?
Yes. Always hearing protection, not only will you hear the grand babies longer (progeria usually hits when you're old but it's from loud behaviors from a lifetime of ear damage) but you'll listen better to what's going on if you're not getting a headache from the constant wind...maybe it's just me with all the head injuries, but it gives me a headache. My buddies with fewer head injuries, who let me talk them into trying some hearing protection, said it was a lot nicer. Carry extra because you'll lose them over-time and you might save a buddy too.