Riding boots are very popular with a lot of long-distance riders. You can find nice riding boots at your motorcycle dealer. You should particularly check out the boots at a BMW dealer and at a Harley dealer. Some people report riding in waterproof boots bought at an army surplus store. I dunno.
Waterproofing is important to some people. Any boot can be made waterproof simply by dipping it in rubber. The better waterproof boots are made with a layer of Gore-tex or some such, so that the boots also breath some and there's some chance of your feet surviving a hot day. If you're choosing a boot for summer riding and you don't ride much in rain, perhaps you would prefer a non-waterproof boot for just this reason. If you ride year-round and want a winter type boot that's waterproof, and you're also going to use it in the summer, I recommend you put a bit of lemon oil, tarragon and sage in your boots: that way, at the end of the day, you can say your feet are poached in a mild lemon, tarragon and sage broth, which sounds a lot higher class than simply saying your feet are cooked.
I ride in the winter in a pair of Teknic Defender Gore-Tex boots that I got at NewEnough.com for $85. In the summer I ride in sandals.
I have not shopped price on the boots below. You'll have to search around on the internet to find the best price. I have tried to find net retailers that each carry a few different brands of boots. Here's some links to some popular brands of riding boots:
If you're looking for boots for casual off-road, for example riding a KLR or V-Strom, you can get very adequate and comfortable boots for about $100. I don't recommend street boots for off-road use: they aren't made to protect your ankles or toes, and they won't last long under this kind of abuse. If you're going to ride off-road, you really do need dirt bike boots. Remember, this is from a guy who rides in sandals six months out of the year. There's a lot of brands of boots out there retailing for $90 - $135. I've put a small sample here. Talk to the kids who ride motocross, they live in these boots and know what works and what doesn't.
If you want a full off-road outfit, boots, pants, jersey, gloves, then buy a Dirt Rider magazine and check for Apparel Package prices. You'll save a whole bunch of money.
If you have a dual-sport bike, you'll likely have to rotate your shift level up a notch to make room for any of these boots to fit underneath.
If you're looking to get 20 feet in the air, you need SIDIs or AlpineStars for about $300. I'm not an expert on getting 20 feet in the air, except for one thing: if you're 20 feet in the air, you have perfect suspension, and you land on level ground, you get a 20g impact. 30 feet = 30g impact. If you weigh 170 pounds, at 20gs you weight 3400 pounds. Oh, and you don't have perfect suspension, so it's actually worse than that.
I ride off-road in O'Neal Element boots the I got at NewEnough.com for $90 including shipping..
Gloves are, in my opinion, a very personal thing. Most riders I know own two pair: a light weight pair for summer riding, and a set of gauntlets for cold weather riding. I ride in bare hands from 60° up. I use FirstGear Supertech gloves in cold weather. If it's really cold, I also use Moose Paws. I have electric grips.
My best recommendation is to go to a lot of motorcycle shops, especially including a BMW and a Harley shop, and try on a lot of gloves. Pick what feels good. For riders, the important thing is warm hands that can feel the controls.
If your primary concern is staying dry, a really outstanding cold and wet weather glove is the Frey-Daytona Voyage, about $150.
It's a good idea to have a few spare sets of gloves around for passengers. I have a set of cheap $10 vinyl and fake fur gauntlets in size medium to loan to women. If you have a SO (or SWAMBO to Brits) who always rides as a passenger, I recommend you take her to a sporting goods store and let her pick out some ski gloves. These are not very good for driving as they're almost always too thick to feel the controls, but if you're not driving they are warmer, more water and wind proof, and cheaper than motorcycle gloves. In March you can get some very nice gloves on sale for half off, typically like $25 for $50 gloves.
Still wearing shirts with little alligators on them? That's soooo passé. Well, now you can have a prestigious
With this belt your kid can fall asleep while you're driving and nothing happens.
Unless you ride with a full-face helmet, you should always have eye protection - even when riding behind a windshield. Ask any optometrist, and they'll be happy to tell you stories of bikers with hundreds of little tiny pieces of rock permanently embedded in their eyes.
You can pick any good sunglasses for daytime riding, of course. At night you need something clear - for example a pair of those cool WWI flying goggles.
If you happen to be suffering the slings and arrows of outrageous aging, you can get bifocal safety glasses quite inexpensively. These are polycarbonate lenses with a reading glass section molded in. They're great for looking at the road, or down at your instruments or map. You can get clear or tinted bifocal safety glasses from several manufacturers for $6 to $12 at Ebay or SafetyGlassesUSA.