Looks that don't work for me

There are always new trends coming out and I try to keep my eyes open for more "everyday" versions of those trends to ensure I get multiple usage and extra wear out of them.  However, there are a couple that I love, but am either too nervous to try or that just do no work on me.

For example,I am IN LOVE with Jessica Simpson's Dany platform. I think they're gorgeous and I love the height and the raw wood look, but I am just terrified to even attempt them-those suckers are TALL.  Another trend that makes me nervous is the bold lip.  Anything really dark makes my top lip look overly thin since it exaggerates how tiny it is! So I def. have to stay away from the vampy lips :( Some other trends that I have tried but that I feel somewhat introverted in is the really wide trouser leg, the Rihanna inspired bold shoulder and the middle (hair)part. I have a fairly deep side part and when I part it down the middle I feel awkward although it is somewhat cute.Also,I have purchased two pairs of wide leg but I think I just want to wait until summer to wear them with sandals or a taller wedge.  I also want to try a self tanner, but I have a serious fear of turning orange.  I've seen it done right and it looks great and I have seen it go horribly wrong and look oompa loompaish, so we shall see. 

Any trends that you like but are hesitant to try??