15 Amazing Plus Size Vintage Dresses To Enhance Your Wardrobe

15 Amazing Plus Size Vintage Dresses To Enhance Your Wardrobe

Luckily, many vintage styles are eternally timeless, and although they might not dominate the shopping mall, you can still find gorgeous retro dresses. These outfits can enhance any wardrobe, and transform your style.

For plus size shoppers, the careful tailoring of vintage dresses (Also check out Vintage Homecoming Dresses You’ll Love) have huge appeal.

We’ve rounded up some of our favorite plus size vintage dresses, to give your wardrobe that Grace Kelly charm!


Tight at the top before flaring out at the waist, the vintage swing dress is a flattering style on every body shape.

Popularized in the 40s and 50s by women hitting the dance hall, the swing dress is a classic look with a touch of fun.

The swing dress got its name from the movement of the skirt, which swings around as you dance.

In the 40s, the skirts were a little sleeker, but by the 50s, an exaggerated flare was all the rage.


The A-line dress isn’t the first silhouette that comes to mind when we picture vintage, but this pretty style was actually invented in 1955 by Christian Dior.

It’s named because the dress resembles a capital A — fitted at the top, with a slight flare at the bottom.

Unlike the sculpted fit and flare of the swing dress, the A-line has a softer silhouette. It emphasizes the bust and hips, while cinching in at the waist.

A-line dresses can be dressed up for evening wear, but the simple lines work for daytime dressing as well!


In the 1940s, nearly every woman wanted to recreate the hourglass shape.

The peplum was a way of doing that, a ruffle of fabric at the waistline that exaggerated the curve of the hip.

Paired with a sleek skirt and nipped-in top, the peplum used tailoring to create a classic finish.

Peplum dresses best compliment an hourglass figure, but anyone can wear a peplum!

The peplum dress is ideal for occasion wear, especially when paired with 1940s slingback heels. 


Sexy, sleek, and sophisticated, the wiggle dress looks like the ultimate in elegant dressing.

But the popularity of the wiggle dress came about for some unexpected reasons!

Fabric was rationed during WWII, causing clothing designers to cut down on skirt size. From this, the wiggle dress was born!

Decades later, the wiggle dress is still as powerful a look as ever.

Creating a shape that is effortlessly sexy, it hugs the body to emphasize your curves.


Everyone was wearing polka dots in the 1950s! This fun print was the most popular design in Christian Dior's famous “New Look” collection, and it found its way from high-end boutiques to everyday dress. 

The polka dot is a print that every single body type can work with ease, and requires no effort to get right.

It adds a splash of fun to formal dressing (Also check out Amazing Vintage Formal Dresses To Enhance Your Wardrobe), and visual interest to casual clothes. No wonder everyone fell in love with the polka dot dress!


Silhouettes in the 1950s were all about exaggerating proportions. Larger shoulders gave way to tight busts and narrow waists, before flaring out to a swinging skirt.

Details such as high collars and big bows were used to add volume in places, while longer sleeves gave a formal finish.

These style tricks can all be used today to create a vintage look that works with your body.

Use bows and collars to play with proportions, and recreate 50s sophistication.


Revolution came to every part of the cultural sphere in the 1960s, and that included clothing!

Gone were the sculpted silhouettes and muted patterns of the 1950s.

The swinging 60s (Check out 60s Theme Party Outfits) bought loose shift dresses, high hemlines, and an abundance of psychedelic florals!

The hippie look was all about freedom, and loose dresses offer plenty of room for natural movement.

Combine with a bright floral to nail the 60s style of peace, freedom, and flower power.


1950s fashion was really a tale of two halves. There was the classic swing dress, where no skirt could be too big.

And there was the elegant pencil dress, which tucked everything in tight for a streamlined finish.

Check out Grace Kelly in Rear Window, to see just how contradictory the shapes were!

A pencil dress oozes sophistication, particularly when worn in a toned down color palette.

The pencil dress is all about the tailoring, with small features such as buttons and bows to add detail.


There is no halter dress more iconic than the one worn by Marilyn Monroe in The Seven Year Itch.

That loose and flowing skirt was made for movement, offering a jaunty look that was freer than the typical swing dress.

It’s easy to see why women (and men!) everywhere fell in love with that halter.

With more flow and less sculpting than a swing dress, the halter dress is a flattering style for summer parties. Pair with a bold red lip for your best Monroe look.


The wiggle dress gets its name from the distinctive “wiggle” it adds to your walk. And that’s a look that is always in style!

Tight all the way from the hips to the knees, there isn’t much room to run about in the wiggle dress.

In the 1960s, the classic pencil shape was updated with contrasting buttons.

This added directional style, and was a move away from the frugal dressing of the 50s (Check out How To Dress Like The 50s With Jeans).


Gingham dresses bring with them an association of summertime, and of relaxing in the sunshine.

In the 1940s, gingham was an incredibly popular pattern, because it was durable, hardworking, and relatively inexpensive.

A 40s style tea dress is a perfect choice for a tea party, or a daytime celebration.

The casual pattern pairs well with the structured shape, for a look that’s both fun and sophisticated.


The scoop neck has been popular for literal centuries, and this look was everywhere in the 1950s.

It’s easy to see why. The scoop neckline was quietly sexy, drawing the eye to the exposed collarbone. 

Today, the scoop neckline is still popular. It’s revealing without actually revealing anything!

Combined with an off the shoulder sleeve, the scoop neck softens the structured formality of the typical swing dress. 


A lot of vintage styling is about adding small detailing to exaggerated shapes. This allows the dress to maintain the silhouette, while still showing directional detailing and personal style.

Bows were particularly popular, and the large bow is a hallmark of 50s style.

Bows are gently feminine, and can be created using the off cuts of a fabric (so, 50s fashion designers could save money).

Bows can also be used to draw the eye to your most flattering features. 


The flapper style was almost completely different from what had been before.

Hemlines were shorter, silhouettes were straighter, and everything was covered in glitz and sparkle. 

The flapper style is an excellent choice for adding some glam to your wardrobe — especially if you plan on going dancing!

Details such as fringe and feathers are designed to move with you.


From films such as The Great Gatsby, you might assume that in the 1920s women were wearing all sequins, all the time.

This isn’t quite true, and the 1920s did make way for some slightly more toned down dressing styles.

Including the bias cut, which first became popular in the roaring 20s, before dominating the 1930s dress scene. 

Bias cut dresses are made using fabrics cut at an angle. By cutting on the grain, these fabrics have more stretch, and a natural flowing hang.

What Vintage Styles Look Best On Plus Size Women?

Popular vintage styles such as fit and flare dresses and pencil dresses look fantastic on plus sized bodies.

The sculpting and tailoring that were inherent to many vintage styles create a flattering silhouette, and add oomph to any wardrobe. 

Don’t let your body shape hold you back from trying your favorite vintage style! If you feel happy in your favorite vintage style, then you look good!

What Dress Styles Were Popular In The 1950s?

There were two trends that really dominated in the 1950s: the fit and flare swing dress, and the tight wiggle pencil dress. Both styles use sculpted shapes to emphasize the silhouette.

And both classic 50s styles look amazing on plus sized bodies! These looks are all about careful tailoring, used to exaggerate curves.

You can also use another classic 50s trick — detailing such as bows and collars to draw the eye to different body parts.

Where Can You Find Vintage Plus Size Dresses?

Vintage-style plus size dresses are widely available, with good selections on websites such as Amazon, ModCloth, and Unique-Vintage.

For genuine vintage clothing, plus size dresses are a little harder to find, but they are out there! We recommend trying sites such as eBay, Poshmark, and The RealReal.

Final Thoughts

Vintage styles can add excitement and elegance to a wardrobe, no matter your size!

We hope this guide has helped you discover some of the best plus size vintage dresses around.

Willa Price