How do you feel about wearing cliche prints/styles?

So, I have been slacking with blogging (as always). If you missed the first post, I will go ahead and tell you again, that it is not in my plan right now to keep up with the blog and post several times a week or anything like that. However, I would like to be posting more.
I have been hung up because I want to post about the projects that I have been sewing, and I haven't been sewing much and what I have sewn, I don't have good pictures of. I am just not a good photographer. :(
But I have decided that I think it is okay to post things that are not about what I am sewing or what I am planning on sewing.

So, this post if just a question post. How do you feel about wearing cliche (overused, expected, etc) rockabilly, pinup, etc. outfits?

I love vintage and vintage inspired clothing, however, certain prints and styles seem very cliche to me. Not that I do not like the style, but it just seems so over done, that I feel almost like I am "dressing the part." It is weird and I am just not certain how I feel about it.

For example, I have a cherry print dress (like this fabric)

 
My husband loves it (which is why I keep it), but I am just not certain about it. I feel like I am dressing up "rockabilly" (just add a red cardigan, heels, and pomp and pony). It is not that I have anything against dressing rockabilly, I actually love a lot of rockabilly clothing. I don't know it is really hard to explain.

Here are some prints/styles that I am just not sure I can feel confident in...

sailor inspired wear

cherries I already mentioned

leopard/tiger print 

even polka dots, gingham, and stripes to some extent!! 

Now, don't get me wrong. I have nothing against any of these companies or any of this clothing. I really like the look on other people. I personally feel odd wearing it. It is weird and I don't really understand it. I was curious if anyone else was like this.