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.
The classic style of the pin-up originates back from the 1940s. Due to the shortages of materials during WWII, this period of makeup is considered the "natural beauty" look.[20] The US was immersed in war-time economy, which put distribution restrictions on consumer goods.[21] General rationing was supported; women applied mild amounts of products. Despite the rations, "Women were encouraged to keep buying lipstick and to send letters to the front covered in 'lipstick kisses' to boost the morale of the soldiers."
Bettie Page was a stunning woman. She looked fabulous wearing an easy pinned up hairstyle – well, then there wasn’t such a definition, women only did their best to move with the times. Bettie did her best to become an example of how sexy a girl can look. She was pretty bold, wearing a perfect hairstyle and nothing more – we mean, she was often spotted almost naked. However, the modern ladies can inherit only the hairstyle from her, adding it to their regular outfits. Here we have some examples of hairstyles that remind us miss Page and her ability to combine a feminine hairstyle with an aggressive hotness.
Other pin-ups were artwork depicting idealized versions of what some thought a particularly beautiful or attractive woman should look like. An early example of the latter type was the Gibson Girl, a representation of the New Woman drawn by Charles Dana Gibson. "Because the New Woman was symbolic of her new ideas about her sex, it was inevitable that she would also come to symbolize new ideas about sexuality."[9] Unlike the photographed actresses and dancers generations earlier, fantasy gave artists the freedom to draw women in many different ways.[10] The 1932 Esquire "men's" magazine featured many drawings and "girlie" cartoons but was most famous for its Vargas girls. Prior to World War II they were praised for their beauty and less focus was on their sexuality. However, during the war, the drawings transformed into women playing dress-up in military drag and drawn in seductive manners, like that of a child playing with a doll.[11] The Vargas girls became so popular that from 1942–46, owing to a high volume of military demand, "9 million copies of the magazine-without adverts and free of charge was sent to American troops stationed overseas and in domestic bases."[12] The Vargas Girls were adapted as nose art on many World War II bomber and fighter aircraft; Generally, they were considered inspiring, and not seen negatively, or as prostitutes, but mostly as inspiring female patriots that were helpful for good luck.[13]
Although pin-up modeling is associated with World War II and the 1950s, it has developed more recently into a subculture which can be seen represented in the styles of some celebrities and public figures. Pamela Anderson was considered the "perennial pin-up" due to decades' worth of modeling for Hugh Hefner's Playboy magazine.[30] The American singer Lana Del Rey, whose style is comparable to that of the classic pin-up model, has performed a song called "Pin Up Galore".[31] Beyoncé has recorded a song titled "Why Don't You Love Me"[32] which pays tribute to the pin-up queen of the 1950s, Bettie Page. The burlesque performer Dita Von Teese is often referred to as a modern pin-up. She has appeared in a biographical film about Bettie Page, Bettie Page Reveals All,[33] in which Von Teese helps to define pin-up. Katy Perry makes use of the ideas associated with pin-up modeling, and has included these in music videos and costumes. The Victoria's Secret Fashion Show can be comparable to burlesque show, whereas their yearly advent calendar can compare to pin-up in general. [34]
Honestly, this look can work for anyone! Since I used a “fauxnytail”, the look will work for anyone who has long enough hair in the front for a roll (about chin-length at least) because it needs to be able to be pulled up into some sort of bun. It really should work with any face shape and be flattering because the placement of the ponytail adds volume which is complimentary to most faces.
Pinup Girl Clothing: Leaning a little more mainstream and rockabilly, Pinup Girl has an enormous fanbase that spans a variety of subcultures and demographics, from hardcore pinup enthusiasts to true vintage hounds to Disney fanatics. The shop always features some kind of sale and carries collections inspired by everyone from Audrey Hepburn to Dita Von Teese that go up to a size 4X.
You can’t be anything but eye candy in vintage inspired pin up dresses with A-line, pencil or circle skirts that dance with your every step.  A wide cinch belt helps define your waist and add a contrasting color to your pinup fashion. The strapless, spaghetti or halter neck pin up dresses are the most popular 50s pinup clothing for summer.  Pin up dresses with sleeves are harder to find however with a little crop or cardigan sweater sleeveless dresses are wearable all year long.

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The best part? The different types of vintage hair accessories are endless. Everything from hair clips with rhinestones and precious gems, to hair bandanas with geometric shapes, delicate floral designs, butterflies and more were all hits of this era. So, incorporate some retro hair accessories into your next fancy hairstyle or even your every day look to get that 50's glamour appeal you're after. 
Modern art – art for the masses, that is – is supposed to be fun and flirty, which is why this collection of American pin-up art is so incredible to scan through.  Regardless of how you feel about the whole idea of Russia and its current state of affairs, you have to admit that this is a new blend of talent that shows off all sorts of things at once.  If you know anything about Russia and their rules, you understand that their Soviet social posters are important in terms of their rigid rules and propriety.  All of that is ridiculed in a tasteful way by spicing them up with pin-up art that really makes you take a second glance at these posters.
The clients you would most likely come across for this style are vintage enthusiasts, pin up pageant girls and burlesque artists, as well as people going to costume parties. There are also always drag queens and the secret “I Love Lucy”-obsessed people from that era who are holding onto nostalgia. Either way, this style is great fun to create and will come in handy when you least expect it, or when you want to embrace your inner silver screen goddess.