Sleek + Simple OR Bright + Bold?

Since I'm contemplating this myself, I'm not really sure what the right answer is. Is it better to buy one kick ass piece (see below) per season and just wear it non-stop OR buy a few basic canvases (the kind that Theory does well) against which you can layer rad accessories and wear all the time without anyone else being able to tell? I saw this jacket and it's all I could think of. Of course it's a bit out there but still pretty cool. It's a conversation starter for sure, but do I want to be known as the girl in the pink jacket (since I'd feel obligated to wear it all the time)? I guess it's the age old question of what makes for an investment piece and when spending money on a design what makes it really worth it? Just a little something to nosh on over the weekend. If you see me in the jacket, you'll know which decision I made. But in the meantime, talk amongst yourselves.

(photo: courtesy of Net-a-Porter)