Fall 2023’s Most Refined Trend: ’50s Ladylike Dressing

Fashion Trends

In this season of understated luxury trends, one style that truly stands out is the ladylike dressing reminiscent of the 1950s era.

What a remarkable and sophisticated period it was for women’s fashion. Our modern interpretation, three-quarters of a century later, is equally exceptional! Its luxurious lines shine through in every silhouette, reflecting the magnificence of this trend.

Feeling intrigued by what you just read? You absolutely should be, as this trend really delivers. It not only lets you create stunning ladylike looks that steal the spotlight but also guarantees longevity in your wardrobe, serving you delightfully for years to come.

In my research on 1950s ladylike fashion, I’ve discovered pieces that beautifully capture that era’s essence. Expect to find dresses, naturally, as they were the primary choice back then, as were mix-and-match dress suits, comprised largely of coordinating knit tops, jackets, and skirts. Though pants of the menswear trouser variety became popular for women in the ’40s (during World War II), women reverted back to a wardrobe of mostly dresses until the later ’60s and into the early ‘70s. Just thought I’d share that fun bit of fashion history with you.

The coordinating tops, jackets, and skirts mentioned above are as delicious as ensembles now as they were in the ’50s. We’ll be pairing them with pointy-toed pumps, and for a modern twist on ladylike dressing, pointy-toed knee-high boots, as well as top-handled bags. I’ve even included a pair of pearl studs (a must-have then and now) and a cashmere wrap for added warmth, enhancing that unmistakable ladylike sophistication. And to complete the look, there’s the very Audrey Hepburn-inspired capri pant and matching ballet flats.

I’m head over heels in love with what you’re about to see, and I’m confident that as you explore these timeless treasures, you’ll feel the same.

So, ladies, let’s dive right into the world of ladylike dressing!

Ladylike Dresses

You’ll notice that these dresses are all about shape – most are forgiving and figure-flattering. The silhouettes exude sophistication and that undeniable “wow” factor. Whether they’re adorned with prints or solids or made of knit or woven fabrics, each piece effortlessly captures the essence of ladylike style.

And as you transition beyond this trend, these dresses will pair seamlessly with sandals and boots, ensuring you turn heads for years to come. These are pieces to love for years, and add to the foundation and versatility of your wardrobe


Ladylike Separates for ’50s-Style Suiting

Now we’ll move on to my favorite category of ladylike dressing—separates. The joy lies in their versatility, allowing you to mix and match with existing pieces in your closet, extending the versatility of each glorious piece.

Tops & Jackets

First, we’ll explore tops and jackets that define this segment of your look. “Wow” is the word that comes to mind as you browse through these selections. Prepare to be enchanted. Which of these quiet luxury pieces will find a place in your magnificent wardrobe?



Skirts & Pants

Next, let’s dive into the separates that complete the lower half of your ladylike ’50s look: skirts and pants.

The skirts are all A-line or full, radiating a truly feminine and flirtatious vibe. In those days, simple crewneck knit tops were the perfect pairing. Today, these skirts, when combined with the shoes and bags we feature, will undoubtedly earn you compliments aplenty! As for the pants, they embody the Audrey Hepburn spirit. Paired with the tops, jackets, ballet flats, and handbags, they create show-stopping ensembles. Have so much fun selecting from these perfect treasures to enrich your existing wardrobe. Wow, wow, and wow some more!

Ladylike Handbags: A Nod to ’50s Elegance

The standout bag style from the 1950s era of ladylike dressing is undoubtedly the top-handled bag. Its chic appeal remains timeless, and many of these bags even offer a modern touch with their crossbody straps, a feature many of us have come to depend on.

Another noteworthy detail is the focus on moc croc, a trend rooted in the ’50s. I recall my grandmother telling me that she had counseled my mother that every lady must have a pair of alligator pumps and an alligator bag. I cherish that story! With this year’s ’50s ladylike trend embracing croc, we’re sharing a piece of that history with you, too. 


Ladylike Shoes: ’50s Style with a Modern Twist

And finally, our journey into ’50s ladylike style concludes with pointy-toe pumps, ballet flats, and a contemporary twist – knee-high boots with a pointed toe. The pointy toes of these shoes and boots will elevate your look to stunning, even magazine-cover stunning! One thing to keep in mind here: if you are leaning toward a grey palette, you’re going to want to accessorize with the various browns showcased here rather than black.

The boots, while a modern take, exude the ladylike chic we aim for with this look. For those who prefer flats, the ballet flats are timeless pieces that pair beautifully with both the pants they’re designed for and the skirts and dresses you’ll find here. Remember how ’50s movies and TV shows often featured ballet flats with circle skirts? There’s a reason for that—it’s a classic pairing!


Summing it all up…

These 50s ladylike looks are pure chic and sophistication. The quiet luxury, timeless in its essence, scream investment pieces you will love and use endlessly. I am still stunned at the sheer beauty and magnificence of it all. 

Literally, happy treasure hunting!

PSSST! Looking for more curated shopping? Check out some of our other recent posts!

Subscribe to Our E-News!

Weekly content and style inspiration curated by Bobbi, with you in mind. This is the one email you’ll look forward to each week—we promise!

Shop My Favorite Retailers!

Use the links below to find the chicest looks for your wardrobe.