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pin curls, I can brush them into a cascade of curls (that sounds so glamorous!) across the back and set a few sculpted curls near my forehead.
As the layers grow out, I still set the same pin curls, but they brush out to softer waves. In this photo my hair is closer to 8 inches long. Nice if you like to style more dramatic up-dos and French Twists.
One thing to consider if you're contemplating a middy-esque cut is how often you plan to set it. I set my hair 2-3 times per week. But if you won't be doing it that often, consider going to a longer length.
Longer layers can be put into a ponytail on the "off" days or worn with the sides pulled back and still have a retro feel. Check out Wild Kat's tutorial on a cute, no-fuss style.
Shorter layers, like mine, tend to look shaggy if left down and not curled. On my "off" days, I make full use of a bandana or snood. Whatever you decide to do, make sure you have a style that you can enjoy and not feel you have to "deal with" each morning. Vintage-styled hair can be worn on a daily basis if you're realistic about your lifestyle and take pleasure in looking your best. Experiment and have fun!