At the very minimum wear a helmet EVERY time you ride. For newbie riders, most accidents occur at low speeds and within a few miles of your starting point. So that "I'm only going across town, I don't need a helmet" idea is bs. It doesn't take much force to crack a skull. Don't be afraid to put some money into gear. Good helmet, good jacket, boots and gloves will set you back a few hundred at least. But even if you spend a grand or two on gear, that is WAAY cheaper than what you'd pay in medical bills and general misery if and when you go down. A $200 jacket will save you thousands in stitches, pain meds, X-rays and who knows what else.