How to Dress Like an Elegant Woman of the 50s
- Isabella Boston

- 3 days ago
- 5 min read
Updated: 4 hours ago
Fashion Outfits & Tips to Be an Elegant Woman of the 50s
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I have always felt that I was born in the wrong era. I love looking at vintage photos; the women look flawless, elegant, and exquisite. From their makeup down to their shoes, these ladies were the epitome of modest elegance.
These women possessed romanticized glamour and an emphasis on ultra-femininity. They embraced and loved being women with all the rights and responsibilities that came with it, without apology. Motherhood was a sacred calling that they nurtured, and they worked hard to make the home a sanctuary for their families.
And to top it all off, these women brought beauty to the world while adding value to it.
But did you know that most women of the vintage era had fewer clothes than we do today? They knew how to shop for less and make informed choices. This allowed them to be well-polished and put together in every situation.
With a little time and effort, you, too, can look like a timeless beauty for any occasion.
How to Dress Like An Elegant Woman of the 50s

The A-line Full Dress: The 1950s era celebrated the hourglass figure with structured undergarments, such as corsets, and full skirts, creating a distinct, curvy, and feminine shape that many people, even today, find flattering and empowering. The fabrics and prints were pastel colors, gingham, polka dots, and floral prints, creating a charming, feminine aesthetic. I recommend at least three A-line dresses/skirts in your closet that you can rotate and mix and match with accessories to always look like a timeless beauty of the 1950s!

The Pencil Skirt/Suit: The pencil skirt is a timeless piece that also gives a nice, feminine silhouette. It elongates the body, accentuates the waist, and streamlines the figure. The high-waisted styles cinch at the narrowest part of your torso, defining the waist and giving an hourglass effect. This skirt is extremely versatile, allowing you to go from work to dinner or to a casual meeting with minimum effort. I recommend having at least one black pencil skirt that you can mix and match with various blouses, tops, blazers, and sweaters.

The Blouse: 1950s blouses were flattering due to their well-tailored fit and feminine details such as pintucks (tiny pleats), bows, and Peter Pan collars. Other classic collars, like boat necks and V-necks, added softness. Like the dresses and the skirts, blouses were cinched at the waist, creating the famous hourglass figure. The styles ranged from classic button-downs and knit tops (twinsets) to more structured designs with puff sleeves or elegant necklines, all designed to highlight a feminine shape. I recommend having a white, black, and beige blouse for your 1950s Timeless Beauty look.

A Twinset/ Cardigan: Twinsets are matching cardigans worn over knit tops and dresses, creating an elegant, chic, and comfortable look. You can also achieve the same classic look by matching a cardigan with your outfit. You should aim to have at least three sets to rotate with your blouses and skirts!

Shoes: Unlike modern shoes, 1950s shoes featured an elegant curve and point: an inward curve to the heel, which elongated the foot and made them appear more graceful. Slingbacks offered a delicate look while elongating the leg, perfectly complementing the era’s cinched-waist dresses and skirts. Kitten heels and flats offered a more practical yet stylish option, giving a comfortable fit with added flexibility. When creating your 1950s wardrobe, choose a style that enhances your unique personality, while reclaiming your inner beauty. I recommend having one basic black pair of shoes and a pair of nude shoes that will go with everything.

Hosiery: There’s a quote that I like: “A woman is never fully dressed if her legs aren’t too!” This was the mannerism of the women of the 1950s. Women wore hosiery for glamour, modesty, and to achieve a fashionable look with smooth legs. Stockings were essential for achieving a well-polished look with dresses, heels, and skirts. Garter belts held them up, but by the end of the decade, the rise of panyhose became a more popular choice. Today, you can wear thigh-high stockings without a garter belt, or with a garter belt, if you choose, that are comfortable and perfect with your retro-style fashion.

A Handbag: The handbags of the 1950s were flattering due to their structured, petite shapes that complemented the era’s hourglass silhouette. They had features like bold metal chasps, shiny hardware, and structured handles that added polish, elegance, and glamour to any outfit. Women coordinated and matched their bags with shoes and gloves, making them integral to a complete look of everyday glamour.

Red Lipstick: Women of the 1950s wore red lipstick as a symbol of post-war glamour, Hollywood allure (Elizabeth Taylor & Marilyn Monroe), and feminine strength. It was an essential accessory for looking put-together, even at home. Today, wearing red lipstick can give you a boost of confidence; it acts like armour, making you feel more powerful, capable, and ready to take on the world! It instantly brightens the face, making it well-polished and elegant. There is a shade of red lipstick for every skin tone; the key is finding the right shade for you!

A String of Pearls: "Pearls are always appropriate" -Jackie Kennedy. Just like with the red lipstick, women of the 1950s wore pearls because they symbolized post-war elegance, sophistication, and traditional femininity. Pearls fitted perfectly with tailored dresses and the era's refined yet accessible glamour (thanks to the availability of cultured pearls). I absolutely love pearls! I wear them every day. They dress up any and every outfit; they will even dress up jeans. You do not have to buy real ones either. It is said that Jackie Kennedy Onassis even wore faux pearls and not real ones. Who knew?
(Shop this look here.)

Photo credit: Pinterest. Hand Gloves: Gloves were an important integral part of a well-dressed woman's wardrobe, akin to wearing a hat. They displayed sophistication and modesty, and were necessary for public appearances. Day vs. Evening: Short gloves (like four-button) were for daytime, while long, elbow-length gloves were for formal evening wear.
Looking like a “Timeless Beauty of the 1950s” doesn’t have to break your bank. It’s about quality, not quantity. With the right items in your closet, you can create dozens of fashion outfits with just a few items. The possibilities are endless!
For more 1950s ideas and outfits, please consider shopping at Belle Poque Elegant Retro & Beautiful Era Fashions.

Author’s Bio
Isabella Boston is a wordsmith and the creator of Bella’s Attic Studio: A multi-media writing platform and storytelling blog specializing in copywriting, marketing, and content writing.
She is well-versed in medical terminology and scientific research with a focus on the areas of neuroscience, immunology, and functional health. She is also a diarist, creative nonfiction writer, and self-published author.
Aside from being a writer, Isabella is a book lover, a language enthusiast, and, most importantly, a woman of God in Christ Jesus.
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