Psychology suggests that the first thing that someone notices about you is your footwears. Shoes are more important. I'd prefer 'em.

There is a childhood fantasy among our generation, who've grown up playing video games and watched as many movies thanks to torrentz. That look like a detective, wear same clothes, smoke those cigarettes and eat food like them. 

I would want this one.

Try something new. Everyone wears the Santa Clause and Iceman costumes in different ways, but that is no surprise. Try to amaze everyone else. Be a protester like the Ferguson one or middle-east, even better, be a Santa-protester. Depends on your creativity.

So you'll know what time it is.

So you'll know what time it is.

It is totally okay as long as you can carry it properly. You should wear what you find comfortable in also knowing the place you are visiting.