Guest Post: Vintage Shopping 101 with Pin Up Persuasion

For years many years I was a diehard connoisseur of strictly vintage reproduction clothing as I found my proportions sadly did not coincide with those of the ladies from the 1950’s. Vintage clothing was something I admired from afar and envied the ladies that had the most gorgeous of collections in their closets. One faithful day, that all changed and I started to discover vintage dresses in my size and I have been building my collection ever since. Yes, it’s definitely a slippery slope and you’re constantly chasing the incredible high when you find that next treasure. Venturing into the world of vintage is like the unknown, there are SO MANY things to know and learn since these garments are well over 60 years old. Today I am going to share an introduction to 1950s (early 60s) buyers guide for those of you who wish to start building your own collection.

Day Wear:

One of the most common styles from the 1950s era is day dresses since women had to be well groomed even while performing household chores. Many of them are homemade or affordable department store brands that have lasted all these years due to quality fabric and craftsmanship. Homemade dresses generally range these days from $40-90+ and with a label $60-$120+. The prices are steadily increasing now that vintage seems to have hit the mainstream and the demand is greater than ever. If a piece has a unique print (novelty print), expect to pay a considerable amount more as there are many collectors out there seeking these fabulous prints. The wonderful thing about daywear, you can wear them just about anywhere and look fabulous in one-of-a-kind clothing.


If you’re like me, I am a HUGE fan of circle skirts! The 1950’s was the mecca for the most stunning circle skirts in every colour and print you could imagine. Vintage lovers can thank Dior for this stunning silhouette. In the late 40’s Dior debuted the “New Look” which emphasized a nipped waist and full skirt.

Designers in the 50’s followed the fashion house’s example. From gorgeous floral, to stunning novelty prints, even Disney favorites like Lady & The Tramp to dazzling Mexican hand painted sequin designs. These often range from $40-$150+ depending on the condition and uniqueness of the print. In fact a Lady and the Tramp skirt just went for $680 on eBay!

The great thing about these skirts, if they are not quite your size often times the button can be moved a couple inches either way or there’s a little trick I learned from a fellow vintage lover: take an elastic band to fasten the waist closed then cover it with a belt. Tada!



The era also brought many Hawaiian inspired prints and dresses, which can go from day to night by accessorizing. These beautiful prints (which have been around since the 30’s) became popular in the 40’s due to WWII and the many servicemen and women occupying the islands. After the war they returned home with their beautiful Aloha shirts and dresses. With airplane travel becoming more common (and Hawaii becoming a state in 1959) Americans starting flocking to Hawaii on tropical vacations. In 1959 a man named Alfred Shaheen started making ready-made shirt and dresses for men and women. His incredible designs, textiles and construction put these garments above the rest.

Oh, fun fact, in 1961 a guy named Elvis wore a red Shaheen shirt in a little movie called “Blue Hawaii”. Highly sought after designers like Surf ‘n Sand (an early 40’s brand of Alfred Shaheen), Kahala, and Kamehamaha along with Shaheen are the royalty of tropical inspired designs and highly sought after. A 1950s Shaheen dress will run anywhere from $200-500+ but truly worth the investment if you love his style. I began my collection a little over a year ago and now the proud owner of 8 Shaheens.



Of note, ladies very rarely left the house without a hat and gloves! Women were even beautifully outfitted to go to the grocery store.

Evening Wear:

There are endless options when it comes to elegant evening wear from the 1950s-60s, they are origins of Old Hollywood Glamour that we all know and adore. First would be the classic fitted hourglass styles, with a hint of flair known as the mermaid silhouette. Whether you have a ball to attend or looking for a fabulous date night ensemble, the possibilities are endless. Beads, sequins, rhinestones, Lurex, satin, chiffon, they spared no glitz or detail.


Cocktail dresses are fabulous affordable options which were commonly worn during social gatherings like dinner parties hosted by the lady of the house. The hemlines are usually a few inches below the knees and/or tea-length with full petticoats. Evening gloves were also a must. In the early 1960’s, the wiggle took front stage over the nipped in waist and full skirts from the 1950s. This is the time where the dazzling sequin fitted dresses were born and very sought after today. These lovely pieces are quite affordable ($40-$100+) despite their very glamourous appearance. Cocktail dresses can range from under $100 well into $500+ depending on the level of detail and overall condition.


When we think of Old Hollywood Glamour, the first thing that comes to mind is breathtaking ball gowns. Ceil Chapman, Suzy Perette, Edith Head, and Dior are just a few of the top in their class when it comes to ball gowns, cocktail dresses and movie costumes. If you want to drool over amazing fashion I highly recommend watching old movies from the 30’s, 40’s, 50’s and 60’s. These designers often only outfitted the very rich and famous. Department stores were the popular place to find fancy dresses for the everyday housewife. As you can imagine, the current price tag for such lavish gowns are reflective of their elegance. For example, a Ceil Chapman dress on the lower end starts at $500 and goes well into the thousands. There are definitely more affordable unbranded vintage gowns within reasonable price range; I recently acquired one on Etsy for $200USD (originally listed at $400).



There are a plethora of timeless vintage treasures to collect from the era we all know and love; swimsuits, playsuits, handbags, jewelry, and so on but it’s best to start off slow, research and build your collection one piece at a time. If you’re unsure if vintage is really for you, or looking for some tip and tricks on how to get started, please visit my post “Venturing into the unknown“. I am always excited to share my new vintage finds on Instagram along with the recent product reviews and features from my blog Pin Up Persuasion.

A special mention to Amber from “Pinup at Heart” who helped contribute the very insightful history portion of this my guest post.

Jessica / Pin Up Persuasion

Categories: Clothing

0 replies »

  1. Pinup Persuasion on Miss Victory Violet?! Love!!! You two lovely ladies are among my favorite bloggers who are vintage enthusiasts! Jessica, I loved all your example of vintage finds mentioned above, especially the strapless green cocktail dress, the print is just beautiful!! Thank you for sharing some tips and guidelines in vintage shopping 🙂

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