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Why Pointed Stilettos?

RoSa Shoes Pointed Stilettos have thinner stiletto heels and more extreme pointed toes than any other shoes you will find. Pointy-toe stiletto shoes, however extreme, are timeless classics. The pointed shoes we see today are inspired by the iconic women's stiletto high heel shoes of the very early 1960s (also known as "winkle pickers"). The term "stiletto" originally referred only to the heel but, as the pointed toe became more extended and refined, it was popularly used to describe the entire shoe.

High Heel Pointed Stilettos by RoSa Shoes - Shop by Shoe Type

The original early-1960s pointed-toe stiletto shoes were considered, when they first appeared, to be the sexiest shoes ever made. However, they were certainly not just fetish items - they were popular mainstream fashion, worn by most smart women for daily wear. At a time when design in general was moving more and more towards streamlined shapes, the long, fine-pointed toes and needle-thin heels were in keeping with the visual style of the Jet Age and represented the culmination of years of development in the craft of shoemaking following the austerity of the 1940s and early 1950s.

In the early "pre-Beatle" 1960s, most stiletto shoes for everyday wear had medium heels of around 3.5 to 3.75 inches, just like our new collection of Medium High Heels. Nevertheless, the more spectacular 4.5 to 5 inch heels (usually exotic, high quality Italian or Spanish imports) could often be seen gracing the feet of those wonderful women who prefer to really teeter on tiptoe, favouring maximum style over mere practicality. These skyscraper stilettos were worn, even around town in the daytime, by those who had mastered the necessary walking technique - usually with the assistance of a restrictively tight just-below-the-knee skirt to keep the stride short and the hips swinging. Running for a bus and hopping up the high step to board the vehicle were just some of the skills which had to be perfected!

(Historical Note: In the 1950s and early 1960s, off-the-peg "straight" skirts were often altered by tapering in the side seams until the skirt became nearly impossible to walk in without high heels. The two items of clothing were designed to be worn together.

Please visit our companion website, "The Little Black Hobble Skirt"   where you can have your very own classic tight skirt made to measure in a choice of fabrics and lengths, from a 1960s knee-length tight pencil skirt down to a true ankle length Hobble Skirt)

High Heel Stiletto Long Pointed Toe Laced Court Shoe by RoSa Shoes


To accommodate the foot comfortably and healthily, a pointed shoe must, of course, extend some distance beyond the natural toeline. Assuming the pointed toe is slender enough not to add bulk and the stiletto heel is high enough to strike a visual balance, a very long point can be achieved - if the shoemaker has the required skills and the wearer has a flair for the extravagant!

As our regular customers are aware, the long, gradually-tapering pointed toe typical of RoSa Shoes designs may at first seem extreme, but it's actually very comfortable to wear.

For many women, the highest manageable stiletto heel coupled with the longest, finest pointed toe represents the pinnacle of desirability. This has always been our aim where shoe design is concerned and we are proud to be able to provide for our wonderful customers - like Rihanna, below, whose style team recently introduced her to RoSa Shoes, the world's supreme example of this type of shoe.

Rihanna wears RoSa Shoes Black Patent Slingback at Billboard Music Awards 2016

A history of pointed stiletto shoes, based on our own personal experience and observation:

The original Italian-influenced stiletto shoes were affectionately known in England as "winkle pickers" because they looked long and sharp enough to remove small shellfish from their shells. They reached their peak of refinement and popularity around 1960-62 but, contrary to what you may read in fashion history books, they continued to be worn by lovers of the pointed stiletto style (despite the mini-skirt/flat boots influence of Mary Quant, Andre Courreges etc.) right through to the end of the 1960s - and beyond.

Variations of the "Stiletto" were worn daily by women of almost all ages and the High Street shoe-shop window displays contained little else. Younger teenagers would look forward to the day they were allowed their first "kitten heel" stilettos with sharp winkle picker toes. The height and pointiness of a woman's shoes were considered an indicator of her stylishness, maturity and sophistication. A whole generation of male observers grew up spellbound by the way women were able to keep their balance on the towering, needle-thin heels and walk without tripping on the extended-point toes. 

The most trend-conscious women in the early 1960s understood the hypnotic attraction created by these shoes and sought out the most extravagant imported styles from Mediterranean countries or specialist shoemakers, like "Stan's" of Battersea, London, who offered to custom-build stilettos with truly extreme pointed toes for fashion leaders of the day. Sadly the advent of mass production eventually priced this kind of personal service beyond the reach of most people and such businesses began to disappear.

Despite the trend in the latter half of the decade for brightly coloured, infantile-looking, chunky shoes, culminating in the platforms and stacked heels of the early 1970s, the longer, sharper, more adult styling of the pointed-toe stiletto shoe never entirely disappeared from the streets. Many women did not see why they should abandon shoes which they and their partners found obsessively attractive merely for the sake of "fashion", and those few independent shops which still had old stock of early 1960s originals found that the demand continued.

Then, in the mid 1970s, something unusual happened. The well-established cycle of fashion suddenly put on a spurt of acceleration. Even before some women had reluctantly given up wearing them "first time around", surviving examples of the original pointed-toe stiletto shoe were brought out of their very brief retirement and reborn as a cult retro fashion item, to grace the feet of a creatively dressed younger generation (often students of design, or women with careers in the media or the visual arts) thus spearheading the Punk-led concept of "alternative" fashion. People had realised that there is nothing sexier or more "rock'n'roll" than a long pointy shoe with a killer heel. Pointed stilettos were big news again - but, thanks to the new mass-production methods, no-one could make them!

Shoe factories and shoe component suppliers, unable to meet (or in some cases even to comprehend) the renewed demand, quickly regretted that they had broken up and disposed of equipment used in the early 1960s, but production methods had changed with the introduction of more mechanisation. The art of making beautiful stiletto-heeled shoes with long, fine-pointed toes had been lost, seemingly forever. The new machinery was only able to produce unexciting shoes with fat, unattractive toe-shapes and thick, moulded plastic heels, so that's what the mass-market fashion industry told women to buy - and the factories duly churned them out cheaply for the High Street shops and their unimaginative provincial customers.

The street-led, alternative-fashion revival movement caused an unprecedented turn around from "passe mainstream" to "cutting edge" status for the pointed stiletto shoe. It led to a craze (certainly in the indoor street fashion markets of major cities like London) for old stock, or even pre-worn, original-style pointed stilettos. Wardrobes and charity shops were emptied and all remaining 1960s stock was cleared from shops and warehouses. Saturday morning in the Great Gear Market, Chelsea was like a feeding frenzy. Obsolete stilettos, many of them high-end designer-quality luxury imports from France and other European countries, were piled high on rummage tables at bargain prices - and those with the highest, thinnest stiletto heels and the longest, pointiest toes were always the first to be sold. All sorts of women - art college students, traditionalist "Sloane Rangers", Punks, Rockabillies, Mod revivalists, Goth Rockers, middle class Mums and many more -  thumbed their noses at the efforts of the modern mechanized footwear industry and opted instead for the superior line and detail of vintage stilettos.

This persisted throughout the late 1970s and into the 80s, by which time the supply of "original" stilettos was becoming exhausted. Contemporary attempts by a few small factories in the East End of London to copy the early pointed shoes (using incorrect heels and dubious toe-lasting) were the only available option. Indoor market outlets like Ad Hoc (of Kensington High Street and King's Road Chelsea) moved over to these new products and the last remaining old stock from the 1960s was bagged up and hidden away in storage. Sarah and I discovered what had happened, sorted through the remaining stock and cleared everything worth having to sell at our first shop in Brighton. We also advertized in the UK trade journals for old stock from the early 1960s and occasionally struck lucky with a retiring independent shoe retailer in some less accessible part of the country.

Nowadays, following this purge of all remaining old stock, even museums of costume and theatrical wardrobe departments don't seem to have any really good examples of those sexy, thin-heeled, ultra-pointed stilettos which a fortunate few of us still recall, clicking and teetering down the street in the early 1960s. Female characters in recently-made movies or television drama set in this period invariably have to wear disappointingly sensible shoes. The camera usually avoids the feet.

Shops concentrating on vintage fashion long ago had to diversify. They now promote the appeal of other eras, e.g. the postwar 1940s and 1950s, or the Glam-Rock 1970s. Shoes from these eras had absolutely no appeal when the Old Stock Stiletto craze was at its height.

So, there are, sadly, no more of the really nice pointy stilettos from the early 1960s to be found. Not in England, at least. They were all brought out of storage in the '70s and early '80s and sold on by the market traders of Kensington, Portobello and Chelsea to fans of "retro" fashion, who wore them until they could be worn no more! Not forgetting our contribution, of course. Our own rather impressive accumulation of over 1200 pairs of "obsolete" 1960s stilettos, gleaned from various parts of the country, was in 1983, according to one leading London vintage clothing specialist, the last significant Old Stock Stiletto collection in the UK - and the shoes were nearly all sold from our first little Brighton shop in less than a year!

We decided from the beginning that the prime purpose of RoSa Shoes should be to recapture - perhaps even to improve upon - the classic, extended-point, ultra-high stiletto styling, using modern developments in component and shoe manufacture which today make possible a more extreme, yet relatively comfortable, shoe. We firmly believe that our shoes are now among the most impressive of their kind the world has yet seen - shoes which, even at the height of the original stiletto era, could only have been dreamed about!