How to Dress Like the 50s with Jeans
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How to Dress like the 50s with Jeans – From oxfords to sweater tees, here are 6 ways to dress like the 50s with normal clothes
This article is all about How to Dress like the 50s with Jeans
In this article
The Fit – Make them High-waisted
01 – Pair them with a Sweater Tee and Cute Shoes
02 – 50s Jeans and Bobby Socks
03 – A Plaid Shirt and Ballet Flats are Effortlessly Chic
04 – Pair them with a Striped Tee and Cute Flats
05 – A Sweater Tee and Belt Dress up your Jeans
06 – Don’t Shy away from Colors
How to dress like the 50s with normal clothes – Taylor Swift
How to dress like the 50s with normal clothes – Diane Kruger
If you’ve ever wondered how to dress like the 50s with normal clothes, then this is the post for you!
If you envy the feminine, 50s fashion for women, but don’t always want to wear a dress or a circle skirt with high heels, then you’ve come to the right place.
50s fashion for women wasn’t only about dresses and skirts.
Although new, jeans were fast becoming a fashion staple and helped gain popularity after being worn by 50s icons like Marilyn Monroe and Grace Kelly.
The secret? It’s all about the fit, the shoes, a great top, and, of course, a defined waist.
Throw in some pastel colors and a red lipstick if you really want to drive the 50s message home.
The Fit – Make them High-Waisted
A common trend you’ll notice in all the picture is the high waist of 1950s pants.
1950s fashion was all about emphasizing the waist, and jeans outfits were no different.
A belt was also often used to emphasize the waist further.
But…as seen by our modern day examples in the end of this article, it is still possible to make a 1950’s inspired outfits with even mid rise skinny jeans.
The key is to bring in other 50s style elements, like pastel colors or red lips.
How to Dress Like the 50s with Jeans #1: Pair them with a sweater tee and cute shoes
Stay comfy and cozy in a sweater tee and jeans, paired with tennis shoes or oxfords like 50s fashion icon Marilyn Monroe.
Ways to glam it up?
Full on old hollywood glamour hair, and her trademark lipstick and eyeliner.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
Lipstick | Cashmere Tee | High Waisted Jeans | Silver Oxfords
Other posts you might like:
15 Sexy Marilyn Monroe Bikini Outfits | Your Sizzling Retro Swimwear Guide
Where to Buy Women’s Saddle Shoes & Oxfords – Your Vintage Shoe Guide
Brigitte Bardot pairs a light tee with high-waisted jeans and belt, showing how a tee and jeans are never out of style.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
Sweater Tee | Belt | Jeans | Shoes
How to Dress Like the 50s with Jeans #2: 50s Jeans and Bobby Socks
“Bobby Socks” referred to the way mostly teenagers in the 1950s would roll down their white socks around their ankles.
They wore their white socks intentionally visible with their saddle shoes and loafers, a trend that still comes and goes today!
Make sure to cuff your jeans to really show off your stylish oxfords.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
Black Jeans | Sweater Tee | Belt | Socks | Oxford Shoes
How to Dress Like the 50s with Jeans #3: A Plaid shirt and ballet flats are effortlessly chic
Take a cue from Lucille Ball on the set of I Love Lucy and pair a gingham shirt with a pair of cute ballet flats and a blazer.
Rolling up the cuffs gives the outfit more of a casual vibe as well as shows off her cute flats.
Although her jeans are looser here, as was common in the 50s, don’t forget the belt to keep the waist defined.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
High-waisted Black Jeans | Belt | Yellow Blazer | Gingham Blouse | Ballet Flats
How to Dress Like the 50s with Jeans #4: Pair them with a striped tee and cute flats
Again, Marilyn Monroe knocks it out of the park with another classic jeans outfit that would look just as stylish today.
The slightly cropped shirt style and high-waisted jeans keep her figure defined.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
High-waisted Jeans | Red Lipstick | Striped Blouse | Red Scarf | Red Ballet Shoes
How to Dress Like the 50s with Jeans #5: Sweater tee and belt dress up your jeans
1950s fashion icon Jane Russell pairs an orange sweater tee and a belt of a similar shade with a dark pair of blue jeans. She also uses a belt to emphasize her curvy figure.
For a modern twist, try an athletic inspired tee with a belt in the same color family.
Shop this “How to Dress like the 50s with Jeans” Inspiration:
Athletic tee | Brown Belt | Red Lipstick | High-waisted Jeans | White Sandals
How to Dress Like the 50s with Jeans #6: Don’t Shy away from Colors
Elizabeth Taylor sizzles in her pair of purple jeans…or are they slacks?
Anyways, with all the colored denim options available, this is an easy and fun look to recreate.
We love how the unexpected color combination looks so stunning on her.
Be creative with purple and yellow, and make sure the waist is emphasized for a true 1950s look.
If you love Elizabeth Taylor’s glam style, you might like:
Shop this “How to Dress like the 50s with Jeans” Inspiration:
Modern Day Examples – How to Dress like the 50s with Normal Clothes: Taylor Swift
Taylor Swift shows us how easy it is to dress like the 1950s fashion with normal clothes.
Looks like she took a queue from Elizabeth Taylor and included some pastel colors!
Love how the denim and the blouse are in the same color family and go together.
What also helps give off the 50s vibe?
The red lipstick and vintage inspired sunglasses.
Shop this “How to Dress like the 50s with Normal Clothes” Inspiration:
Sunglasses | Pink Blouse | Brown Jeans | Red Lipstick | Brown Oxford Shoes
Modern Day Examples – How to Dress like the 50s with Normal Clothes: Diane Kruger
Diane Kruger puts her own unique spin on dressing like the 50s with modern day clothes.
Notice the blouse, tucked into the jeans and the oxfords.
Love how she adds the fedora and the statement oxfords to give it an extra vintage nod.
Shop this “How to Dress like the 50s with Normal Clothes” Inspiration:
Fedora Hat | White Blouse | High-Waisted Jeans | Oxford Shoes | Sunglasses | Green Coat
This article was all about How to Dress Like the 50s with Jeans
Which jeans outfits are your favorites?
How do you like to dress up your jeans?
Other posts you might like:
Marilyn Monroe Gentlemen Prefer Blondes Outfits – All her Gorgeous Glam Dresses
Lauren Bacall Pants – How to Wear Pants like an Old Hollywood Glamour Star
The Ultimate Guide to Poodle Skirts in the 1950s
Marilyn Monroe How to Marry a Millionaire – Your Guide to 1950s Glam
Originally published Dec 01, 2021. Updated Sep 03, 2024
