Pinup can be a great look, and can be really classy. There are some great clothes available too by retro-inspired brands like Pinup Girl Clothing. One of the best parts of these retro looks is that pencil skirts, button down tops, circle skirts and sweaters can be dressed up for a night out or made perfectly work appropriate.
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The thing that really can make or break the look though, (in my opinion) is the shoes. I know that really shocks you, this being a shoe blog and all.
But really, a pair of shoes can complete a look or send everything to hell, and when you're trying to create a specific look it's even more important.
If you're trying to look like an extra in Mad Men, one safe shoe will always be the peep toe. The classic peep with red polished toes is a can't lose, and can be paired with anything from skirts to pants and look amazing.
When choosing heels, if you're going for an authentic look then choose something without a platform and with a low to moderate heel. I don't mean kitten heel, but the six inch heels aren't necessarily historically accurate.
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Wedges are also an option, but need to be exercised with a little more caution. A pair of fun wedges can look great with some capris, but with a circle skirt it can make your lower leg look a little bigger than it really is and creates a blocky look at the bottom of your leg.
Looking like you're wearing cement blocks on your feet is never good.
Pinup is an easy look, it's a good look, and it fits girls with almost any body type (but please buy clothes in your real size- fitted not tight), and you can wear so many different type of shoes. As long as it's something sleek, and heeled, anything else goes. Color, print, vamp, pitch, pick what you like because it's all fair game. Just remember to sway your hips a little when you walk. A little hip sway can go a long way no matter what you're wearing.