CLASSIC ’50S WOMEN’S FASHION LOOKS & HOW TO WEAR THEM TODAY

When it comes to building a distinct style, few tactics compare to gathering iconic pieces from the past. The vintage fashion of the ’50s is a perfect source of inspiration for adding a retro touch to any wardrobe.

Some garments have proven timeless as the decades press on, and they persist in style-savvy wardrobes year after year. Among these perennial favorites lie some of the ’50s’ most iconic items: pencil skirts, cardigans, cropped sweaters, and silk scarves. Recent years have seen a push toward cozier, oversized styles—’50s clothing provides a standout way to add a bit of structure to an ensemble.

Today, designer labels merge vintage-inspired silhouettes with modern sensibilities and their brand motifs. This amalgamation generates refreshing new designs that bear subtle reminders of days gone by.

We’ve rounded up some of the most iconic pieces from ’50s women’s fashion and created combinations that can breathe new life into these cherished designs.

INTO THE TIME WARP: WHAT DID PEOPLE WEAR IN THE ’50S?

Renowned for changing women’s style in the ’50s, Christian Dior debuted his first collection entitled “New Look” in 1947, offering a range of garments focused on the female form through hourglass shapes and rounded shoulders. The collection featured generously gathered fabric skirts, form-fitting jackets, and stunning dresses. This monumental shift from conservative wartime styles to billowing forms encouraged an aesthetic of celebratory glamor.

As the decade progressed, women’s fashion provided a wider range of options, allowing a greater expression of individuality. This shift gave women alternatives to mainstream, ultra-feminine silhouettes, catering to rockabilly, pin-up, beatnik, and greaser sensibilities.

To revisit this post-war fashion renaissance, explore these ’50s-inspired garments that still make waves today:

Pencil skirts

An icon of the era, these slim-fitting skirts typically fall at or slightly below the knee. The silhouette was donned by some of Hollywood’s most glamorous stars.

Silk scarves

Silk scarves add a pop of texture and color to any outfit. Although they were worn prior to the ’50s, the scarves introduced during the mid-century boasted exquisitely bold prints in luxurious fabrics. Tie them around the neck as an accent or wrap them around the head, knotting them at the nape, to keep hair in place.

Swimwear

Another memorable facet of ’50s fashion was swimwear. One-piece swimsuits often featured sweetheart necklines, ruching, and thick halter straps. Regarding two-pieces, bottoms were often high-waisted, and tops sported wide bands and full coverage.

Circle skirts

Voluminous circle skirts took center stage in the ’50s, most notably with the archetypal poodle skirt. The circular pattern allows the fabric to fall naturally, creating graceful waves and gathers that accentuate the hips and narrow the waist.

Pedal pushers

Pedal pushers paved the way for modern-day capri pants. This casual style is fitted, calf-length, and comes in various fabrics. The tailored silhouette makes them an excellent fit for loose blouses and voluminous peplum tops.

HOW TO DRESS LIKE THE ’50S

Playful colors and exaggerated shapes pioneered in the ’50s have made their way back into popular fashion. Cinched waists and face-framing silk scarves are on the rise, granting ample opportunity to incorporate classic motifs into an everyday fashion repertoire.

Try these refreshing looks to take a contemporary approach to ’50s style:

Peplum top + pedal pushers + kitten heels

Create a monochromatic look with a pair of brightly colored pedal pushers and a sweet peplum top. Complement the ensemble with kitten heels and a structured clutch. Embellished bobby pins or barrettes add a modern twist.

Button-up shirt + knee-length pencil skirt + mules

Pencil skirts highlight the figure, making them an alluring option for most dressy outfits. Start with a long linen or cotton pencil skirt in a solid shade and loosely tuck in a white button-up top. Complete the look with matching mules, a structured leather handbag, and a thin gold bracelet. For cooler weather, layer on a timeless beige trench coat.

Cropped cardigan sweater + long maxi skirt + ballet flats 

Cropped cardigans are making a comeback, as style influencers pair them with jeans, leather pants, wool trousers, and skirts alike. To give this classic piece a modern twist, style it with a straight-cut skirt and vibrant ballet flats.

Silk scarf + cashmere sweater + printed pants 

Silk scarves up the elegance of every ensemble. Tuck a cashmere sweater into gingham or checkered pedal pushers, then wrap a colorful silk scarf over the head and tie it under the chin. Complete the look with sunglasses, a small watch, bobby socks, and loafers.

Tailored suiting + Oxford shoes

Take a page from the tailored suiting of the ’50s for a modern matching outfit. Although women’s sets of the past typically comprised a suit jacket and skirt, a coordinating pants set takes a contemporary approach. Select a set in an exciting color or print and tie it together with a pair of black Oxford shoes and a small handbag.

Evening dress + jewelry + heels

The designer evening wear of the ’50s is second to none, with romantic floor-sweeping gowns crafted from exquisite fabric. For this look, don a long, formal satin dress with a Queen Anne or off-the-shoulder neckline, and accessorize with an extravagant necklace of pearls or diamonds. Finish the look with matching earrings and evening heels.

Collared shirt dress + wicker tote bag + sandals

The shirtwaist or house dress was a quintessential item in any ’50s housewife’s dress rotation. Nowadays, the shirt dress offers modern women an updated take on this classic. Choose a short-sleeve pastel pink, blue, or white shirt dress with a wrap-around waist to create an hourglass shape. The cinched waist accentuates the figure while keeping the fabric loose and comfortable. Accessorize the outfit with a wicker tote bag and strappy sandals.

Halter swimsuit + sunhat + sandals

The right swimwear enhances every beach day. Select a style in a vibrant hue with ruched fabric or a structured underwire-enhanced bodice. Complete the look with a wide-brimmed sun hat, designer sandals, and a canvas tote.

Turtleneck sweater + circle skirt + heels 

Balance the billowing fabric of a circle skirt with a form-fitting and sophisticated turtleneck sweater. Pair a solid-color turtleneck with a floral or tweed skirt, tuck it in neatly, and finish the look with a pair of simple heels and an envelope clutch.

TIMELESS STYLE, CUTTING-EDGE ADVICE

Regardless of what current fashion trends dictate, one’s style should always feel unique. Whether it’s a statement coat or bold shoes, designer clothes help you stand out from the crowd and make your mark.

For more inspiration and styling ideas, dive into the editorial archive at Neiman Marcus, where we provide insight into fashionable combinations that will leave a lasting impression for decades to come. Learn all about beautiful everyday necklaces, cocktail hour conventions, and how to create ’90s-inspired looks.