1) Roller blades. I definitely give credit for this idea to that new HP Printer commercial, you know, this one with the super-cute baby and Melanie song. It's been stuck in my head all day. And it got me thinking, I don't see anyone roller skating anymore. I used to have a pair--the kind with brakes on the front, which, in retrospect, seems less than safe--but how cool would it be to skate around as a method of transportation? Especially fictionally.
2) Quills. Yes, it's very Harry Potter (which makes quills all the cooler), but in a contemporary setting, quills would definitely air on the quirky side. Imagine the issues that could arise from spilled ink or broken feathers...
3) Envelopes. Maybe he/she collects fingerprints or trace evidence to document his/her life. maybe he'she leaves notes sealed in envelopes as a means of communication. Maybe they hold his/her many different flavors of gum.
Any ideas for quirky items/habits?