What Inspires Me About ’50s Dresses

by Sammy in 6 Comments — Updated January 7, 2020


I don’t own any 1950s dresses — not even one!

So when I decided to model these five ’50s dresses from Hinesite Vintage, I wasn’t just excited — I was anxious. I didn’t know how the ’50s styles would feel and flow on my body. Would I feel awkward, or worse … would I look it?

While I turn more regularly to the styles of the ’60s and clothing of the ’70s, I opened my mind and my heart to the potential that somewhere in me was a ’50s girl waiting to be unleashed.

And in opening my perspective to this potential, I began to muse on how fashion can actually make us better people because when our creative limits are pushed, we are moved to grow!

The creative challenge these dresses presented proved fruitful in the end, because rather than focus on the styles of the dresses I focused on their stories instead. Like spirits, these dresses had past lives, and I felt as though I were breathing new life into each as I wore it.

So to show you how ’50s fashion goes deeper than surface-level, keep reading after the jump to not only see these 5 vintage dresses from the ’50s but to feel how their styles inspired new thoughts in my mind and love in my heart.

Vintage lovers are a special community because unlike mainstream fashion, there are no specific vintage “trends.” You can be a pin-up princess hanging out with a ’80s rocker and still feel that special bond because you are both wearing vintage!

I know that so many of my readers are ’50s clothing lovers, and so I wanna know: Which of these ’50s dresses inspires you the most?

Let me know by leaving some love in the comments below, or saying hello on TwitterFacebook or Instagram

xx, SD


Sunflower ’50s Tea Party Dress

50s sunflower print dress

50s sunflower dress

bow tied sleeve on'50s sunflower dress

sunflower print

Dress Available from Hinesite Vintage

THE STYLE: It’s an easy-to-wear (and being cotton, easy-to-wash!) dress with a softly flared and pleated A-line skirt that falls below the knee.

Its short sleeves are styled sweet with darling knotted bows, and a shallow V notch exposes a touch of skin.

These sunflower designs remind me of Van Gogh, as if a dressmaker saw his famous sunflower painting and declared she must pay homage to his work with this dress!

THE STORY: Have you ever seen The Help? This dress reminds me of something a lady of that movie’s era would have worn to an afternoon tea and cards session.

Perhaps she’d have worn a hat with matching sunflower applique, and she’d most definitely have worn her finest pair of starch white gloves with some matching canary yellow pumps. My grandmother used to play bridge with her friends regularly, and I’m sure this dress was something she once had in her personal collection of the ’50s!

THE INSPIRATION: The bright sunflowers of this dress reminds me of our inner light within and capacity to help those around us to find their own gorgeous rays of light, too.

I believe that we feel better about ourselves when we radiate love, appreciation and compassion for the people who come into our lives (especially the strangers). I call this “shining your light” because you can use your feel-good energy to help others see past their own darkness.

Even when someone is treating you unfairly, you can radiate kindness in return. The more love (“light”) people with darkness receive, the less likely shadows in their life cast gloom.

Candy Stripe ’50s Picnic Dress

1950s candy stripe pink dress

50s candy cane striped pink dress

pink'50s sweater

candy cane pink striped pattern

Dress Available from Hinesite Vintage

THE STYLE: It’s a candy cane striped sundress made with a matching pink sweater. The square neckline is a nice point of difference compared to other ’50s styles.

Plus, the smock bodice emphasizes the chest, adding some pin-up pizazz to this pretty girl dress.

THE STORY: I imagine this dress and sweater set worn on a cold summer night at the drive-in movies with your sweetheart!

Or perhaps the dress’s sweater comes off (uh oh!) when you and your guy hit Lovers Lane. It’s such an iconic ’50s image, and I can’t help but see this style worn in such a scene!

THE INSPIRATION: This dress reminded me of my inner child because of its innocently sweet and approachable design. Give me this dress and a swing set, and I’ll push my dreams high because I believe in the goals of childlike me!

Ever ask a group of 6-year-olds “Who can sing?” Most of them will raise their hands with a resounding yes!

Ask that same question to the same children when they’re 12 years old, and watch that ratio drop in half. By the time they’re 16, only a fraction truly believe that “they can sing” — even if at 6, they had answered “yes.”

As we age, we become more jaded and hardened to life’s possibilities. We forget to dream without inhibition. That’s why I think it’s important we channel our inner child as much as possible, because the child within reminds us that anything is possible.

 Bowed Blue ’50s Prom Dress

50s blue bowed prom dress

50s Blue Bowed Prom Dress

blue bow on 50s prom dress

pleated blue chiffon material on 50s prom dress

Dress Available from Hinesite Vintage

THE STYLE: It’s as classic as ’50s prom dresses get, complete with a waist bow and layers upon layers of iridescent blue chiffon.

The dress nipped my waist so tiny that I felt it had a built-in corset. Thankfully I could breathe just fine, even giving it a few spins for transformation into Prom Princess!

THE STORY: Prom dresses are supposed to embody every girls’ “dream dress,” and this one embodies the divine in that dream!

Visions of a ’50s prom are about as cliche as they get: Couples awkwardly slow dancing with one another in front of a stage with a sparkling disco ball above. Teacher-chaperones stand off in the shadows, keeping eye on the punch bowl so that no one “accidentally” spikes it.

In this vision, I see my date wearing a matching baby blue tux and a pair of thick-rimmed glasses. Oh, what a dream boy!!

THE INSPIRATION: Speaking of prom, remember how uncomfortable high school was? Even I — Miss Sammy Sunshine! — moped away high school listening to the morose vocals of Sarah McLachlan, Jewel and Tori Amos.

I smile looking back at those moments of 16-year-old insecurity. My fears never manifested themselves, and here I am today chuckling at the boys, the drama and the uncertainties I felt so emotionally attached to.

I try to keep this attitude in mind whenever I’m feeling down, because I can immediately bring peace to my heart when I remember that what seems so bad today won’t feel the same way tomorrow. Just like that teenage angst!

Plaid ’50s Secretary Dress

black and white plaid'50s dress

50s black and white plaid dress

faux pockets on a 50s black and white plaid dress

the black and white plaid pattern on a'50s dress

Dress Available from Hinesite Vintage

THE STYLE: It’s a curve-hugging wool dress designed with classic black and white plaid print. The print turns criss-cross style on the faux (meaning you can’t put anything in them) waist pockets and along the neck.

While it’s knee length on me, the short sleeves and high neck give the dress a conservative edge in line with typical  ’50s style.

THE STORY: While conservative in coverage, this dress is certainly cut with some sexy sass. I love how it nips in at my waist and gave my tush a little wiggle when I walked!

I imagine Joan from Mad Men owned quite a few of these dresses in the purples, reds and black/white shades that suit her office vixen look best.

THE INSPIRATION: Comparing this dress to something an “office vixen” would wear had me thinking about the stereotypes we place on people we don’t even truly know, and how society impressions us to turn to archetypes to explain what “type” of  person someone is.

When we judge others, we are saying it is OK for others to judge us, too. I believe that the less we judge others, the more we are loving ourselves because we’re not projecting negativity onto anyone or anything that could potentially bounce back to us.

I can’t say I’m always judgement free, but the less I form opinions of others and treat them with selfless love and compassion, the more positive our relationship is.

We are all brothers and sisters on this planet. Joan, you are perfect just the way you are!

Lace ’50s Wiggle Dress

'50s blue lace wiggle dress with cape overlay

'50s baby blue lace wiggle dress

neck tie of'50s baby blue lace overlay

baby blue lace pattern on'50s dress

Dress Available from Hinesite Vintage

THE STYLE: It’s my favorite dress from the shoot! An ice blue floral lace layers over a skin-colored slip to create a sexy wiggle cocktail party dress complete with a matching lace overlay that buttons at the neck like a cape.

This dramatic look shows off the arms and bust with just the right amount of cinch for a teeny tiny waist!

THE STORY: I’d love to know where this dress was originally worn — but all I can do is transport myself back in time with my imagination!

I see its previous owner standing tall at a cocktail party, shoulders back with a sleek martini in her white gloved hands and a fun loving grin on her face. I don’t think she’s married … perhaps she’s eying up the boys at the bar!

She’s rocking some costume jewelry bling in her ears, drawing attention to her perfectly coiffed beehive only made possible thanks to the wonders of hairspray!

THE INSPIRATION: This dress made me want to dance! It reminded me of the quote, “You’ve gotta dance like there’s nobody watching / Love like you’ll never be hurt / Sing like there’s nobody listening / And live like it’s heaven on earth.” 

Heaven on earth is when we dance our own dance by pursuing our passions while living on this planet. Without fear of what others think of us, we can dance the moves which come most naturally — and happily! — to us.

I rocked “the swim” in this dress, and maybe in another style I’d do the worm!

Whatever your dance, bust out those moves and I promise: Others will join you because dancing is the party of living your awesome life. 


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Thank you to Hinesite Vintage for loaning vintage clothing for the creation of this article.


STYLE: The Ladylike Trends of 1950s Fashion
MODERN: Why the 1950s Style is Popular Today
CELEBRITY: What Marilyn Monroe Wore in the ’50s
HOW-TO: Wear a ’50s Shirtwaist Dress 4 Unique Ways
OUTFITS: 3 Easy Ways to Rock ’50s Fashion Now
TRENDS: The Top ’50s Clothing Trends for the Modern Lady

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DRESSES: Get Vintage ’50s Dresses on Etsy!

6 thoughts on “What Inspires Me About ’50s Dresses”

  1. So hard to choose! My style is more about the drama than the sweetness so have to pick the blue chiffon!
    Also love the one with the blue lace- love the layers!

    • hi Jenn! Thanks so much for stopping by and commenting! The blue chiffon WAS drama! So epic to play with and twirl (and tight!). Love your site — I need to check back and scroll around some more ;-)

      xoxo Vintage love!

  2. I love the pink dress and sweater set. What I like most about it isn’t the fabric but the way it’s cut. It looks like it would work on an hourglass figure really well with that high and wide middle/waist band. As a separate note, may I quote your note about the six-year-olds and singing? It’s so true!

    • Hi Gretchen! These are great points! The wide waist band is a good fit for hourglass figure. Thanks for bringing that to my attention ;-) As for my note about singing … WE CAN ALL SING!!! xoxo

  3. I would love this dress with a pair of retro loafers.

    • hey Janet! I’ve actually never come across a pair of loafers that are older than the ’80s! Remember the weejun styles? Thanks for stopping by and commenting! xx Sammy


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