"A floor pump makes maintaining tire pressure easy. Pumps that are stored on your bike are useful when out and about, but take longer to get to the desired PSI. This pump features a smart head, meaning you don't have to think about whether your tires have presta or schraeder valves - just connect and start pumping."
"Sure, you can get a toolset with lots more on it, but for everyday use, this one has everything you'll need. Park Tools are built to last. The 5 and 6mm allen wrenches are particularly useful for common adjustments. This is the one I keep in my seat bag."
"An amazing helmet light - perhaps the single best thing you will purchase for night riding. The light output is incredibly bright (it has three settings: bright, less bright, blinky) and it moves with your line of sight. This is, hands down, a great way to be seen at night. Worth every penny."
"If you ride at night, you need more than a light that helps others to see you. You can find more powerful headlights, but unless you are really riding through super dark places (i.e., the woods at night) this one does a great job. Also waterproof, which is useful."
"If you don't want to clip in, these are a great alternative. The pins embedded in the pedals grip your shoes, and don't rip the soles. Very useful for riding in cooler weather, when your shoes are larger and may not fit into toe clips."
"My wife makes fun of me for how much I love this jacket. Light, thin, windproof, and will keep you warm down to around 20 degrees. It wasn't made specifically for biking (and I wear it for just about anything), but it sure does a heck of a job!"
"Riding with a helmet is a must. I can say with confidence that this helmet saved me from brain damage when I was involved in an accident, so I can't help but include it on this list. Of course, your head may be shaped differently, so go for one that feels most comfortable."
"Take care of your chain and it will take care of you. This system makes it easier to clean your chain. When the provided cleaning solution runs out (and it will after two or three chain cleanings), head out and get a gallon of Simple Green."