How to Dress Pin Up Everyday – Pin Up Style History

Get the “Pin-up” Look

Basic Pin Up style tips for work-days or weekends

There is no doubt that pin-up styles that harken back to the mid-20th century are appealing because of their charm and innocence. With cute, flirty, curve-loving fits, pin-up fashions are easy to translate into today’s world.  But, what about the history of the style and what about having the right pieces to establish a fully stocked pin-up wardrobe?


A Brief History of Pin-up Style

Think of the most iconic pin-ups such as Marilyn Monroe, Betty Grable or Rita Hayworth and you think killer heels, red lipstick and pulled-up curls with bangs to flatter their foreheads. Wearing a polka dot bikini or an A-line dress, or even black stockings and garter belts (Betty Page style) they were considered pin-ups because their posters were meant to be torn from movie magazines and pinned to a wall.

Swing Dress

You could go ahead and fulfill your pin-up fantasies wearing your favorite style, but you can also make that style toned down and ready for everyday wear with a few key pieces.


Piecing together the Pin-Up Wardrobe

In the 1950s, A-line dresses were the rage. Introduced by designers like Christian Dior, these dresses are still in style. Wear them to parties, wedding receptions, or special events. They feature a narrow waist with a skirt that flows outwards like the bottom of a trumpet.

Pin Up Style Dress

Another important piece is a pair of cigarette pants. These taper at the ankles and feature high waistlines. Start with black so that you have a tailored look you can easily pull off at your next meeting. These are also cute enough to pair with vintage bamboo-handled purses, cat-eye sunglasses and an oversized straw hat with kitten heels for a Saturday stroll.

Cigarette PantsPedal Pushers


Tops and blouses can be of solid colors but choose a few where a little bit of décolleté is visible. This way you have those which you can wear on the weekend and those you can wear with your cigarette pants to work.

Pin Up Outfit


Cropped sweaters are also a plus if you want to look like a true 1950s model. Choose pink for extra femininity.

Pink Cropped Sweater

For any of these above-mentioned staples, you can also incorporate colors and patterns. Flowers, cherries and polka dots are extra vintage!

Cherry Cardigan

And don’t forget to match your nail varnish and lipsticks for that complete look.

Baby Pink Nail Varnish


To create a pin-up fashion look any day of the week for any occasion, you have to have the right shoes. Bring together an assortment of high heels in black or red patent leather along with open-toed sandals, kitten heels, and flats. Start your collection with the basic solids like red, black, white and navy.


Gloves are for the die-hard 1950s style lover, and why not add them to your look? There was a time where women dressed up just to do the grocery shopping – at least that is what June Cleaver seemed to do. While her character never quite made it to pin up territory she was very au currant for the late 1950s in her styles with white gloves for a dinner out with her husband or for running errands.


Headbands are also great accessories to have on hand. Roll a bandana up and tie in a bow at the top. Place around your head and you have instant pin-up worthy hair that you can show off even while painting a garden fence. For this type of weekend activity, you will want to wear a pair of rolled-up Levis and an oversized men’s shirt.


The Complete Pin Up Look

Get the complete pin up look below and you will be well on your way to channeling Betty Davis or Marilyn Monroe – strike a pose!

Pin Up Style

Achieve this look by pairing a vintage flared dress with a cropped cardigan and Mary Jane style pumps. Finish the outfit with a matching clutch purse and oversized sunglasses. And don’t forget your eye lashesnail polish and lipstick. The pin-up style is one that has fallen in and out of fashion. But, in today’s ever-changing world, women like you want to keep this innocent but fun look alive. You can do it with these pin-up style tips and some essential pieces.

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