Katy Perry rocks these do's all the time and it totally works for her. If you've got the confidence and the wardrobe to compliment then I say go for it!!
And of course, I have to mention my favorite hollywood icon, Marilyn Monroe who does the short hair pinup look...
Also, a fun thing to do for an instant pop of glam is add a flower to your pin-up hairstyle. It is so easy to make these fake flower headbands: simply find some fake flowers at a craft store or online and hot glue them onto a simple headband and voilla!
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