Old Hollywood Valentine’s Day Outfit Ideas and Inspo for Women
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Old Hollywood inspired Valentines Day Outfits for women including 1950s Valentines Day Pinup, 1940s Vintage Valentines and Old Hollywood Glamour Valentines
“Love is in the air… or is that just the smell of chocolate?”
This post is all about vintage-inspired Valentine’s Day Outfits from the 1940s-1960s
Looking for the perfect Valentine’s Day outfit for either a cozy night in, a Galentine’s Day Brunch with the bff, or a special evening out with your handsome someone?
Get inspired by these Old Hollywood Valentines Day outfits….think luxurious fabrics, feminine silhouettes and statement jewelry.
Find the perfect Valentine’s Day outfit you’re looking for, whether it’s a romantic lingerie style, a 1950s valentine pinup style, a feminine pant outfit, a chic two-piece skirt suits, or a full-on vintage glam evening gown.
Yes, even the pant styles are feminine, thanks to inspiration from fashion icons and Old Hollywood stars like Marilyn Monroe, Audrey Hepburn, Grace Kelly, and Elizabeth Taylor.
Ready to recreate a romantic and timeless look for the season of love?
Raise the bubbly, and let’s go girls!
Valentine’s Day Outfit Ideas: 1950s Valentines Day Pinup
Ready to set hearts racing in the most unexpected Valentine’s Day outfit ever?
How about digging into the vintage pin-up aesthetic?
Valentine’s Day Outfit Options: Two Piece Pin-Up Style
What better way to celebrate the day of love than a daring two piece pin-up style?
Who knew that retro themed pin-up outfits could be so sexy and festive?
What a fun look for either a girls night in or Galentine’s Day party.
Boys beware: or you might get the “point”, or find that bullseye target is your heart!
P.S. Isn’t Marilyn Monroe’s (top right) red heart garter just to die for?
Valentine’s Day Outfit Ideas: Pin-Up Styles – Skirted Retro Swimsuits
Two of the most famous pin-up models ever, none other than Marilyn Monroe (top left) and Rita Hayworth (top right) pose for some iconic Valentine’s Day shoots.
Both gorgeous Old Hollywood leading ladies opt for the ultra-feminine (and very popular) vintage skirted swimsuits.
Did someone say… legs for days?
Marilyn Monroe pairs her strapless skirted swimsuit with strappy heels, while Rita Hayworth opts for an au natural look in a tippy toe pose to further elongate her legendary legs.
Marilyn Monroe’s Valentine’s Day snap was to promote her upcoming 1952 film We’re Not Married.
Marilyn Monroe fans will notice she’s wearing the same swimsuit that’s on the cover of the film!
As for Rita Hayworth, is she about to jet set to Buenos Aires to practice her ‘almost striptease’ in the sizzling film noir Gilda.
For more on popular pinups, you might like:
20 Wildly Popular 1950s Pin Up Models
The Golden Age of the Pinup – Pin-up Girl History and Style
Valentine’s Day Outfit Options: Pin-Up Styles – One Piece Vintage Swimsuits
Why wear a boring pair of jeans, when you could sizzle in a Valentine’s Day themed swimsuit?
These Old Hollywood beauties’ red and white vintage swimsuits with heart poses just ooze with nostalgic charm.
Talk about an easy pin-up style to recreate.
Simply style your hair in retro waves, add a touch of make-up, and find a fabulous feminine vintage swimsuit.
And… of course, don’t forget your heart props!
Whether you want to sit on your heart, like a queen (Lila Leeds), hold it in your hand, while you stand on a fuzzy rug (Ava Gardner), or step through it, like a gateway into an enchanted land (Rhonda Fleming), the options are endless to recreate this vintage Valentines aesthetic.
No hair accessories or jewelry is needed for this look.
Plus, for shoes, chic white ballet flats, low red pumps, or bare feet (let’s say with red nail polish) are all fab options.
Get the ultimate inspiration on retro swimsuits:
How to Rock the Vintage Swimsuit Aesthetic like an Old Hollywood Glam Star
Valentine’s Day Outfit Ideas: Pin-Up Styles – Ruffled Mini Dress
The stunning red head Arlene Dahl captivates as The Queen of Hearts. (top left)
We heart her fabulous vintage pin-up mini dress in rosy hues.
Are you able to recognize the blonde cupid, (top right) before your heart is run through?
It’s none other than the #1 Pin Up Model. Ever.
It’s the one and only Old Hollywood supermodel who insured her legs for over one million dollars!
None other than Betty Grable.
To recreate this retro style, say goodbye to the little black dress, and hello to the frilly vintage short dress.
Opt for reds, pinks, whites, and retro Valentine’s day props to channel this one of a kind pin-up style.
Valentine’s Day Outfit Options: Vintage Lingerie
Get ready to set hearts racing in these vintage feminine lingerie styles….
Plus, everyone knows that eating chocolates in… slinky lingerie, is just so much more fun than… in yoga pants!
We can definitely learn a thing or two about lingerie from Old Hollywood.
Which do you think would best highlight your figure, and play up your unique essence?
Is the sexy sheer black robe, or the silky silver two piece set more your jam?
Or maybe you just wanna dress up as a mysterious someone on February 14th!
There’s something undeniably thrilling about a double-life. Just ask the lady in silver.
“I guess I lead a double life, and I must admit I’m happy with both.” — Yvonne De Carlo
Need more Old Hollywood glam lingerie inspo?
Sexy 1940s Lingerie – Bombshells & Vintage Bra Styles
1950s Vintage Lingerie: Retro Bras & Pin Up Underwear
Valentine’s Day Outfit Ideas: Everyday Styles
The next category of Valentine’s Day outfits are everyday styles that are, oh so perfect, for February 14th.
Chic, comfy, and not over-the-top.
Plus they are easy to dress up or down.
Valentine’s Day Outfit Ideas: White Pants Outfit with Pink Accents
Leave it to Audrey Hepburn, famous for her timeless and elegant style, to provide the ultimate inspo for a feminine pants outfit to add to your Valentine’s Day Collection!
In the 1957 romantic comedy, Funny Face, Audrey Hepburn stuns in her chic casual style, as she sails the Seine river in Paris.
Audrey Hepburn is wearing white cigarette style slacks, with a cropped white blazer.
What sets off the outfit is the pink silk tie belt that emphasizing her figure, and also matches her the same silk tie in her straw hat.
Plus notice how her pink flats are the same shade.
Looking for more feminine pant inspo from Old Hollywood?
1950s Women’s Pants Outfits – 7 Chic Vintage Styles
Valentine’s Day Outfit Options: Classic Tailored Skirt Suit
Looking for a stylish everyday outfit that not only travels beautifully from the office to Happy Hour, but also is festive for Valentines Day?
Say hello to the classic tailored skirt suit!
First Lady Jacqueline Kennedy (below) one of the most enduring fashion icons, wears a stunning burgundy skirt suit during a televised Valentine’s Day tour of the White House in 1962.
“I’ll be a wife and mother first, then first lady” — Jackie Kennedy
Tips to recreate this timeless style?
Opt for a classic 1960s structured skirt suit with statement buttons.
Pair this with pearls, a glittering bracelet, voluminous waves and tasteful make-up.
Other classy ladies from Old Hollywood also selected the the versatile skirt suit as their go to look for Valentine’s Day.
Barbara Billingsley, famous as the quintessential suburban housewife in the 1950s-1960s popular TV sitcom Leave It to Beaver, looks smart in her chic skirt suit with fur detailing. (above)
What do you think of her son’s (“Beaver”) homemade vintage valentine card?
Audrey Hepburn, posing as cupid in this early 1950s photoshoot, also selects a skirt suit as her outfit of choice for the day of love.
At the time she starring in Gigi on Broadway, and was relatively unknown.
Little did she know that only the next year she would win an Academy Award for her breakout role in romantic drama, Roman Holiday.
And the rest, as they say is history, and Audrey Hepburn officially became America’s Sweetheart.
She didn’t miss a heart with her cupid’s arrow.
To channel this classic Audrey Hepburn style, opt for for a figure skimming two piece skirt suit and pair this with simple jewelry, including door knocker earrings.
Valentine’s Day Outfit Ideas: Classic Shirt and Skirt
Looking for other classic feminine everyday outfits that are perfect for special occasions, like February 14th?
Two stunning Old Hollywood blondes, Marilyn Monroe, (top left) and Marilyn Maxwell, (top right) show just how timeless the white blouse is.
Option 1: Opt for an off the shoulder peasant style, like our beloved blonde bombshell, Marilyn Monroe, shows off, in her vintage heart cutout.
Option 2: Select a button-up peplum style, with embroidered hearts, like the 1940s-1950s actress and entertainer, Marilyn Number II, aka Marilyn Maxwell wears, as she steps out of a Valentine’s Day chocolate box.
(How do they think of these props? Haha.)
Of course the classic pairing of white black and white, with red accents is also an easy and chic style that travels perfectly from the office to happy hour.
Opt for a white blouse that will skim your curves (baggy and shapeless are no no’s!). Pair this with a black midi skirt.
We heart the red accents in the matador look.
Red belt, red heart, red hair ribbon, and red lipstick.
Oh yes, and to up the drama, opt for one black glove and one white glove. Sizzle.
Add some sheer black stockings and black ballet flats, and you’re ready to find Zorro or Tornado (your famous black horse)!
Valentine’s Day Outfit Options: Old Hollywood Glam Styles
Looking for a dressy outfit with a big wow factor for your special night?
We’ve got you covered (literally).
Time to move onto the formal Old Hollywood glam styles.
Valentine’s Day Outfit Options: White is the New Little Black Dress
On Valentine’s Day the White Dress is the New Little Black Dress!
A curve hugging white slinky floor length gown with silver metallic heels is a great option.
(Bonus points if you re-create the life sized velvet red heart.)
Valentine’s Day Outfit Options: Floor Length Formal Gowns
When it comes to “Frills and Fluff” on Valentine’s Day, go big or go home.
Puff sleeves in baby blue and flowy, fluffy ballgowns were so in when it came to romantic Valentines Day formal styles.
Since the dresses steal the show, there is no need for even simple jewelry.
Plus, it’s always a great idea to practice your Kodak perfect pose in front of a giant Valentine’s Day heart.
If you’re invited to a royal ball on V-Day, you can always opt for a princess style evening gown, like the one Princess Grace wore to the Monaco palace! (bottom right)
We love the pastel shade of her stunning sleeveless ballgown.
Hold the frills on this one, only a “fluffy” glittering translucent shawl, tied in the shape of a bow is in order.
Notice her simple jewelry, which is fit for a princess.
The only thing that’s missing is… her prince and tiara!
Read more about Grace Kelly’s famous real life romance:
Grace Kelly Engagement Ring – Her Stunning Ring & Fairytale Romance
Oh, speaking of tiaras and Valentine’s Day outfits, we have just the perfect style from none other than Audrey Hepburn.
In another unforgettable scene in Funny Face, Audrey Hepburn models the perfect Valentine’s Day outfit, as part of the French fashion collection.
We love Audrey Hepburn’s unique and feminine two piece white and pink evening gown, with a train.
This is beautifully paired with white gloves, white shoes, and a diamond tiara and diamond earrings.
Of course in the film, the audience breaks into applause, as Audrey Hepburn strolls down the catwalk in this outfit.
Itching for more pink outfit inspiration? You’ll swoon for the “Think Pink!” opening sequence in film.
For more on Audrey Hepburn’s fashion in Funny Face:
Audrey Hepburn Funny Face Dresses – Her Sensational 1960s Fashion
And, drumroll, for one of the most famous pink dress in cinematic history, also known as the “Marilyn Monroe Pink Dress.”
It’s no wonder this dress has been the inspo for copycats and parodies, from Madonna’s Material Girl number, to the iconic Barbie, to countless Halloween costumes.
In the 1953 movie Gentlemen Prefer Blondes, Marilyn Monroe’s gorgeous pink dress rivals the glittering diamonds, that she wears while performing her iconic “Diamonds Are a Girl’s Best Friend” number.
Notice another big pink bow, and how it totally works!
Marilyn Monroe’s dazzling strapless evening gown is in a bright sugary pink silk fabric.
Her accessories?
Matching pink opera gloves and a “Girls’ Best Friend”.
Yes, lots and lots of statement diamond pieces, from earrings, to tiered necklaces, to bracelets…
To learn more about all Marilyn Monroe’s fabulous 1950s outfits in this film:
Marilyn Monroe Gentlemen Prefer Blondes Outfits – All her Gorgeous Glam Dresses.
Valentine’s Day Outfit Ideas: Red Old Hollywood Glam Evening Dresses
But that’s not all ladies…
On the hunt for a dream dress, that’s not pink or white, to usher in your Valentine’s Day gala?
Look no further than the one of a kind red chiffon gown, that the gorgeous Elizabeth Taylor wore in The Last Time I Saw Paris 1954.
The translucent straps, glittering bodice with a sweetheart neckline, and full floor length skirts in deep red sizzle in the ultimate Old Hollywood Glam style.
Looking for a red formal dress for your special occasion that is also stunning and unique, but is a little more structured?
Audrey Hepburn teams up once again with Givenchy for an unforgettable Old Hollywood formal dress.
To recreate this stunning style, select a red figure skimming silk tube evening gown, with a long red train, and matching red silk wrap.
Pair this with stylish and comfy red low-heeded kitten pumps.
Add long gloves in white for a pop of contrast. And don’t forget to add a retro statement necklace and earrings.
This post was all about Old Hollywood Inspired Valentines Day outfits, from glam floor length gowns to casual styles.
Which Valentine’s Day styles were your favorite?
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