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There are exactly three things a woman needs in life: a great dress, her best high heels and a shade of lipstick to put the fear of God in a man’s heart. A great pair of heels is the perfect complement to an unapologetically feminine pin-up or wardrobe.

The funny thing is that heels weren’t originally designed to be feminine. Quite the opposite, in fact – they were a men’s shoe. Try picturing men of today in stilettos. It’s a funny image indeed, and a pretty far cry from the pin-up girl.

Keep reading to see how to claim high heels as a staple of your pin-up wardrobe – and how to choose the best high heels for your outfit.

A Short History of Shoes

First things first: heels weren’t originally made for women. What’s that about?

The First High Heels

Well, at their inception, heels weren’t actually meant as a fashion statement. They were made for functionality.

I know, right? Picture the modern stiletto as something functional. Doesn’t work, does it? But that’s because the heels of bygone years didn’t look like the heels of today. Once upon a time, heels acted more like foot support and were located in the middle of the foot.

Heeled shoes first gained popularity in 15th century Persia, where they were a favorite among male equestrians, specifically soldiers. The heel helped a soldier maintain a secure stance when he stood in the stirrups, which allowed him to shoot more easily.

The Higher the Shoe, the Further the Sh*t


When messengers from Persia began traveling to Europe, they naturally brought their heels along. Kings weren’t interested in the heel for equestrian purposes, but high heels did have another benefit.

They raised your feet above the filth on the street – mud, muck, horse manure, etc.

The Best High Heels in a Man’s World

High heels also had another function in this period: indicating status and, later, wealth. Women’s platform shoes are thought to have originated in the Venetian chopine, an 18-inch-high platform used by prostitutes to quite literally rise above their rivals.

Courtesans – the highest class of prostitutes in this era – also had access to things that many of their rich, “respectable” female counterparts did not. That’s because their profession was to entertain men and they interacted primarily with men.

This provided them access to traditionally “male” areas and interests, including libraries and, yes, high heels. Many courtesans would accessorize their best high heels with men – that is, they enlisted four or five noblemen or one of their male servants to act as a human crutch.

Imagine enlisting the men in your life to be your living crutches for the day.

Fit for a King

In the 18th century, high heels were a favorite of Louis XIV, the French king who stood at a mere 5’4″. Heels had been worn by kings for centuries – not as a fashion statement but as an intimidation tactic.

Stories of Henry VIII, a man of 6’2″ in the 1500s, often refer to his height. Kings who towered over others were kings implicitly regarded as more frightening, more godly.

For Louis XIV, it was a symbol of power. Louis was the first to popularize the red-soled shoe, and courtiers in his trusted circle were also allowed to wear red soles as a symbol of status. Imposters who painted their soles red to indicate false closeness to the king were thrown out of court if they were caught.

Heels were also a sign of affluence precisely because they were impractical to walk in. Having high heels was like having clothes made of voluptuous fabric, something wildly unsuited to everyday use.

They were a sign that you didn’t need to walk because you didn’t need to work either. You were there to see and be seen.

Making the Modern Stiletto

Fast forward a few centuries to the post-WWII era. Enter Christian Dior.

Dior is credited with bringing back the French high heel in the 1950s by raising the heels on court shoes and making the shoe more ornate. Who exactly invented the modern stiletto is up for debate – some say it was Salvator Ferragamo, others credit Roger Vivier.

Either way, the stiletto is a precision piece. The heel is made by using injection molding to encase metal spigots in plastic so that a heel the size of a tack was safe for women to stand on.

The Best High Heels for Your Style

Choosing the best high heels isn’t just a reach-and-grab operation. Especially when you’re aiming for the 1950s pin-up look.

High heels are a fashion statement, so when you pair them with your outfit, you need to think about what statement you’re looking to make.

If you’re looking for a casual dress to present a sleeker, simpler look, then your shoes can act as your bold statement in your outfit. On the other hand, if you want the focus to be on a big floral print or playful polka dots, your shoes can be understated to keep the attention where it belongs.

Check out our six tips for a vintage-inspired look, then keep reading to pick the best high heels for you.

Types of Heels

The high heel has a rich history, and it shows in the available styles. Especially when your best high heels are looking to complement the 1950s pin-up style.

We know the 50s was a time of experimentation with the high heel, especially for women. When men came back from the war, women were using shorter heels for better day-to-day functionality at work, where they had to move more freely. As women returned to domestic life, higher heels became the rage.

For a true 1950s pin-up look, try one of these styles to find your new best high heels, from the classic court shoe to the edgy winklepicker to the ageless peep toe.

Stiletto-Heeled Opera

The stiletto-heeled opera shoe was made to make a statement. At their most extreme, these shoes could be four-inch-tall, ultra-thin spiked heels.

Stilettos are named for the Italian knife – a fitting title because the shoes were deadly not just for stepping in sidewalk grilles. Men were justifiably afraid on dance floors, almost as much as the owners of said dance floor.

In the early 1950s, these heels had a small metal cap at the end. And that wasn’t anything to mess around with – back in the day, these shoes were known to leave dents on softwood floors. They weren’t allowed in museums and courthouses for that reason.

They also featured a V-shaped cutaway from the side of the shoe, and if you were in the mood to make a statement, red was the color of choice.

As you can guess, these were highly impractical shoes reserved for statement-making moments – worn to make an entrance and take off later, or by fashion models.

Court Shoes

High heels aren’t just for kings these days. Thus: the court shoe.

As the name implies, these shoes were first popularized in royal courts. These are also the type of shoe that Christian Dior modified to bring the high heel into the 20th century.

These are also a practical choice as your best high heels for day-to-day wear. They tend to be kitten heel-height and up, and the size of the heel can vary from chunky to slim depending on the style of the shoe.

This makes court shoes versatile, depending on the style of court shoe you buy. If you’re looking for a good set of heels to pair with a variety of outfits, stick to a classic-looking court shoe.


Don’t let the funny name fool you: the winklepicker was the underground’s best high heels.

This is a style notable for the elongated, pointed toe. The winklepicker is a dramatic version of the opera heel (which, by the way, is hardly a wallflower.) It was worn in the 50s by Teddy Boys and rock n’ roll fans.

And like rock n’ roll, the shoe was a symbol of the anti-establishment.

The pointed toe was meant to be menacing. And rock legends like the Beatles helped cement it in rock history after the winklepicker was first popularized by the Mods.

Want to make a cutting fashion statement? Winklepickers are the heel for you.

Kitten Heels

I know, I know. I can see you cringing from here.

Listen: Audrey Hepburn knew kitten heels were the best high heels for breakfast at Tiffany’s. She was probably on to something.

Comfortable footwear is in – see the recent athleisure trend. As far as high heels are concerned, kitten heels are a dream.

They’re easy to walk in, ridiculously practical and, when worn right, insanely stylish. Remember Audrey Hepburn? The style icon? She knew a few things about fashion.

Women in the 1950s knew it too. When they had to leave home for work during WWII in men’s absence, they turned to kitten heels because tottering around in tall, thin heels was wildly impractical.

Heels were still thin, of course, because fashion was still the name of the game. The fashion-savvy kitten-heeled woman had shoes in leather, suede or soft reptile skin, with jewel tones for evening parties.

Baby Dolls/Mary Janes

For your vintage-inspired best high heels, you can’t do better than baby doll heels. Every woman in the 50s had at least one pair, preferably black.

For running around the house, the lower, thicker-heeled baby doll style was more practical than the kitten heel, which was still designed with fashion in mind (but make no mistake: Mary Janes are no schlub’s shoe.)

In the market for a great pair of Mary Janes? Check out ModCloth’s selection for your next best high heels.

Peep Toe

Few shoes are as classic and iconic as the peep toe heel. If you need a pair of timeless high heels to add to your rotation of best high heels, the peep toe is a great place to start.

The elegance of a peep-toed pump lies in the execution and being willing to break a few style laws as needed. For example, “thou shalt not pair thy open-toed shoes with thy hosiery.”

We all shudder with dread at the thought of becoming the old man at the end of the street who mows his lawn wearing socks and sandals. Don’t let it keep you from pairing your peep-toed pumps with tights because a peep-toed pump shows just enough that you can get away with it.

Just avoid open, strappy sandals.


For an iconic shoe, you can’t go wrong with wedges.

As far as practical shoes go, wedges will also take you a long way. They’re chunkier by design, and because the heel is joined to the toe, they’re wonderfully easy to walk in.

But they still give the heel that nice lift that acts to shape your legs.

Back in the 50s, wedges were taller and designed to curve inwards a bit more, along with a half-inch platform in the sole. This makes them more delicate than many modern wedges, which wear their clunkiness as a character trait.

Plus, nothing quite says “vintage pin-up girl” quite like a good wedge.

Perfect Your Pin-Up Style

For the vintage fashion icon and the curious newbie, don’t worry. Choosing the right dress for your best high heels is an adventure. We’ve got your back.

We’re a trusted seller of 1950s-style dresses – and it shows in our happy customers leaving five-star ratings. Why? Simple: we keep one eye on our dresses and one eye on the current trends in vintage-inspired fashion.

We also love seeing your vintage-inspired style flourish to be uniquely yours. Our blog is full of our best tips, tricks and ideas for a great vintage style, including the 10 retro accessories we can’t live without and the essentials for every pin-up-inspired wardrobe.

Vintage and pin-up styles are uniquely feminine and bold – that’s what makes them so much fun for the modern fashionista. Let us help you get out the door stylishly with our bold corset dresses or playful striped dress.

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