I think this is a great look for a beginner or someone with an advanced skill set. The best advice I can give when it comes to creating rolls is, when you think you’ve teased it enough, tease it a little more. I find that most people are afraid to tease their hair. With vintage styling, I find teasing key. I recommend using a texturizing power like Puff.Me at the roots then teasing with a “C”-shaped motion. Lightly brush out the surface and use a pomade or wax to smooth flyaways.
Using a little light back-combing along the way if you need to, and spraying some hairspray along the way will help, guide the hair so that it starts to curl around, using your fingers to help guide the strands in place. When in position, hold with bobby pins, and if you have blonde hair, use blonde pins to ensure they’re not too visible. Black pins look very obvious sometimes and can spoil the look. Spray with hairspray, pin the remainder of the hair up, and add a scarf for a real pinup touch.

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