Pinup Girls: 15 Ultimate Secrets to Dating the Elegant Icon

Dating pinup girls isn’t as straightforward as dating other girls. Here’s what you need to consider when dating a pinup girl to not fall flat on your face.

pinup girls

Think pinup girls, and already you’ll be conjuring images of sailor’s tattoos, Rita Hayworth, and all that coiffed hair. But one thing is for sure, whatever size pinup girls come in, they’re all curvy, voluptuous, and just plain va-va-voom!
And if you think you want to try to get into the culture and fancy yourself a pinup girl for a girlfriend, then you have to learn that it may not be as easy, breezy as you think. Those kinds of girls are into pinup for a reason. You may have to put in extra effort to be noticed, considering their discerning tastes.
So, what is a pinup girl anyway?
Before you decide you want to go seduce the next Betty Paige, get yourself familiarized with what the pinup culture is all about and why pinup girls dress the way they do.
The pinup girl is a classic Western icon admired by men and emulated by many women for her beauty and sense of style. It started in the 1800s when women started to be more independent, wearing boots and bloomers instead of skirts and petticoats. Therefore, looking more masculine and 10 times more sexual. Soon after, many artists and illustrators created images of voluptuous, hourglass-figured women with lush hair and full lips.
The war in the early 1900s spurred propaganda to entice men to join the military forces. It used images of women playfully wearing military getups. 1920s came and the flapper generation began, where women wore shorter hems and even shorter hair.
However, the quintessential pinup didn’t start until the 40’s, when illustrations of sexy and enticing All-American women were “pinned up” by soldiers in their barracks to boost their morale. Soon after the war was over, everyone figured using images of voluptuous half-naked women was a good marketing move—and the rest is history.
How do you date pinup girls?
#1 Find them in their habitat. First of all, find a pinup girl. If you don’t know one in your immediate vicinity, then you can go to car shows, vintage shops, and similarly themed events to find a pinup girl. Usually, pinup girls model for photographers and in car shows, so you won’t go wrong there. [Read: Where have all the women gone?! 10 places to meet them]
#2 Try looking online. If you still can’t find one, try online *Duh! You can find almost everything there*. There’s a dating site for almost anyone with a particular preference or fetish. There’s also a growing community of pinup girls online, so you won’t lose your way.
#3 Learn about the culture. Once you get to talk to pinup girls, you have to have some substance, especially when it’s about the type of things they’re into. You have to know about their culture, so you should make researching about it your homework.
#4 Talk the talk. Pinup girls have a lingo. If you approach them with some lousy pickup line, and they say, “Are you writing a book?” don’t think they’re the least bit interested in you. They’re actually telling you to back off. Pinup girls today like to use lingo from the 40s and 50s as part of their culture—and that’s how you know they’re authentic rockabilly chicks. [Read: 30 foolproof pick-up lines & 10 you should never use]
***By the way, rockabilly is a type of music in the 1950’s (think Gene Vincent’s “Be-Bop-A-Lula”), which has also taken a revival along with pinup culture, wherein the pinup clothing and hairstyles are popular in the era. So moving on…
#5 Let them take the lead. Pinup girls are tough. Just because they live like their world is stuck in the 50s doesn’t mean they take shit from guys. In fact, that era was when women became independent from men and became more empowered. So expect pinup girls to be more assertive and dominating.
#6 Ditch machismo. Take it from Rosie the Riveter. Pinup girls do things that men can do—even better. And you can say the same for the pinup girl you’re dating.
If you want to get her attention, be chivalrous, but don’t be a misogynist. Don’t ever think women are the weaker sex, because she’ll definitely prove you otherwise.
#7 Be patient. And not just normal patient. Be extra patient. This is because pinup girls take a longer time to get dressed. Aside from the beautiful hairstyles that take hours to make, there’s the issue of clothes. Many pinup girls wear vintage clothing and vintage fittings underneath those clothes, if you know what we mean.
Cinching their waists with corsets, wearing thigh-high stockings, and of course, those petticoats. If you want a sexy treat, why not just watch her get ready for your date instead.
#8 Step up your game. Be dapper. You don’t want to be looking like garbage beside your pinup date and make people wonder what the heck she’s doing with you. Of course, you have to step up your style game too.
If you can’t rock a pompadour, at least get yourself some dark jeans and a thin shirt with the sleeves rolled up, some high-cut boots, a leather jacket, and you’re good to go. Or better yet, just get that pompadour. [Read: 23 hacks to be a lot more attractive to women instantly]
#9 Embrace her curves. The pinup culture is all about celebrating the natural female form, all those curves and shapes that come in different sizes. The hourglass figure is a pinup girl’s thing, so be sure to compliment her on her ample bosom, her thin waist, and her round hips.
#10 Accept her quirks. She probably has quirks that make her unique compared to other girls you’ve dated. She likes things a certain type, so don’t judge her for it. She may even have her own taste in music, and her home may even look like straight from some 50s furniture magazine. Well, you liked her look, you might as well like everything that went along with it.
#11 Don’t forget your individuality. Don’t get lost in all the culture. You have to continue to be yourself and be comfortable in your own skin—heck, even if being pinup is not really your thing.
While you accept her preferences and the whole pinup look, you have to talk about making compromises early on in your relationship if you want to keep dating her for a long time. [Read: 15 compelling reasons to date an artistic, creative person]
#12 Don’t forget to have fun. Even if she’s into pinup, the point of you dating each other is to enjoy each other’s company. Accept her as she is, and you can be sure that she can accept you as you are too, even if that means you’re into hip hop and dress like a gangster. The main thing is to not forget to have fun and share some laughs.
#13 Compliment her. She spent a significant amount of time putting her look together. She coiffed her hair and put on her makeup, and it may have taken her a longer time than other girls.
As for her clothes, pinup-style dresses are harder to come by, so she may have ordered them online or sifted through many vintage stores. Win her heart by complimenting how ravishing she looks. [Read: Sugar, sugar: How to sweet talk a girl & make her melt]
#14 Gift her with the things she loves. Since she’s a pinup girl, chances are she likes vintage clothes and antique stuff. So if you want to gift her, you at least have a pretty good idea of where to go to buy her stuff. Don’t forget those lingerie, garter belts, corsets, and stockings. After all, you’ll enjoy it too when she takes off her clothes.
#15 Love her for what she is. No matter how similar or different you two are, the fact you’re seeing each other shows how much you care for each other. You’re attracted to her as she is to you, so don’t forget that behind all the pinup makeup, hair, and clothes is that amazing woman you hugely adore.
[Read: What men think impresses women and what actually does]
Despite their tough exterior and that entire gorgeously elegant pinup look, remember there is a woman inside that wants to be cherished and appreciated, so don’t forget to show her that.

Liked what you just read? Follow us on Instagram Facebook Twitter Pinterest and we promise, we’ll be your lucky charm to a beautiful love life.

Tiffany Grace Reyes
Tiffany is a wordsmith who has played with words ever since her letter-to-the-editor was published nationally at the age of 9. Since then her writing has gone f...
Follow Tiffany Grace on