How to Dress 1950s Pin Up Style.

I couldn’t make it to Wintersun this year so as a consolation prize, I wrote the following article for their magazine – it will be particularly useful to ladies entering the Miss PinUp Australia contest or anyone who’d like a bit of help putting a pin up style together.

My favourite pin up – Marilyn Monroe looking smashing on the beach.

How to Dress 1950s Pin Up Style.

Here are some quick hints on how to dress like a pin up model from the 1950s – a look that can work for ladies of all ages and all occasions. The pin up is fun, cute and sexy – she combines the best of elegance with girl-next-door charm and friendliness and is always well behaved, unless she’s being cheeky!

First, determine the fashion silhouette that will suit you best – the two basic shapes are fitted bodice with full skirt (great for younger ladies, pear shapes and slim body types) or fitted bodice with fitted skirt (more flattering for older ladies and curvier figures). Both have advantages – the full skirt is great for dancing and getting blown up by the breeze, to show your pretty scanties beneath. The fitted skirt is sexier, more “bad girl” and shows off seamed stockings to good advantage.

Next, consider where and when you’re going to be – perhaps it will be an informal day location like the beach or garden, in which case your fashion options will include swimwear, sundresses, playsuits, shorts and top or maybe pedal pushers or Capri pants worn with flat or high heels.

Every Pin Up needs some accessories with which to pose and play with – sun hats, towels, baskets, sun screen, head scarves, beach balls, books and sun glasses are great for the playful outdoors model.

For a dressier day occasion like lunch, shopping or a wedding, the ‘50s Pin Up likes to wear a plain or printed dress of cotton, wool or rayon, particularly fetching when worn with a matching jacket (known as an ensemble). This could be ramped up with glamour essentials of short gloves, hat, and necklace with matching ear rings or brooch and perhaps a neck scarf too. Her heels of course, will be high.

Underneath her frock, she wears her best lingerie: suspender belt with seamed stockings, small and/or frilly knickers and a structured bullet bra or long-line bra (e.g. Merry Widow) or perhaps a corselette (lightly boned corset, nothing too arduous). Her lingerie will be made of either satin or lace, and her favourite colours are black, white, red and pink.

Next on the style list we have dinner or cocktails – a simple evening gown of silk, brocade, taffeta or velvet is accessorised with long gloves and a small evening handbag of fancy materials. For special occasions, consider a small dark hat with a veil. Her jewellery is more elaborate and sophisticated but the overall effect is understated. Her outfit is complete with a dry martini.

When she feels like pulling out all the stops, the Pin Up model loves to frock up in a full length ball gown complete with the longest (opera length) gloves, and elaborate jewellery. Around her bare shoulders she might drape a fur or fabric stole – her outfit is completed with a small and fancy handbag and a well-dressed man.

Ladies, follow this simple guide and you will always be perfectly dressed and ready for posing!

(This article originally appeared in the Wintersun magazine, June 2011 and is reproduced with their permission. Copyright remains with Nicole Jenkins, please request permission before reproducing).


  1. Hello there , I need some advice on how to dress vintage for vacation and how to do my hair casual but also fancy,An also can i wear like pink lipstick or so i just stick with red ?

  2. Hi Melissa, thank you for your enquiry: it’s a bit hard to answer without knowing anything about your hair, colouring etc – if you’d like to come and see me sometime I can give you some advice. Can you email me at nicole at circavintageclothing dot com dot au? Thank you.

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