This is something I've been working on for a bit: minor dares.
These are dares that you can safely do without utterly breaking social convention.
As I'm rather shy, this is a good thing for me.
The basic principle of the dare is that you only get to wear one layer of clothing. All clothes have to contact the skin directly.
You have two options:
You get the underpants and undershirt of your choice, and that's it. This is a good option for not going too far from home.
This one's a bit more picky. You get a button-up shirt, and a pair of jeans or similar. Both should be a size or so too large. You only get to button 2/3 of the buttons on the shirt. This one seems simple, but once you go anywhere you'll start feeling a lot more naked than you look. Keeping your clothes on will require conscious effort.
This is my first dare issued, so I don't really know if it works. Be honest, please!