Who's the best-dressed Briton in history?

I saw David Bowie (1947–) for the first time on the 1973 Aladdin Sane tour. I was nearly 13 and it was the first time I’d been allowed to go to a gig by myself. The instant Bowie came on stage, with his shock of red hair and sporting a huge pair of platforms, it was as if an alien had landed. I left the gig utterly blown away by Bowie’s music and style (and already planning a change of hair colour): that gig marked the start of a lifelong obsession with music and fashion.

There’s no doubt that Bowie changed youth culture, and he certainly had the sort of rare gift for predicting and anticipating fashion trends that could have made him a designer in his own right. Northern soul, punk, post-punk, new romantic… he was always on the cusp of changing fashions.

One of Bowie’s most iconic outfits was the huge-legged striped bodysuit, designed by Kansai Yamamoto, worn on the Ziggy Stardust and Aladdin Sane tours of the 1970s, which helped bring Japanese clothes design to the forefront of fashion. Bowie’s clothes were works of art that were the result of his vision and creativity, and as memorable as his music.

The fifth-longest reigning monarch in British history, Henry III (1207–72) used art and fashion to enhance his authority, and is the first English king for whom we have detailed household records describing the purchase of clothes and jewellery. As well as containing detailed descriptions of the king’s coronation and burial garments – fashioned from red samite, a heavy gold-embroidered cloth – they also reveal Henry III had a keen eye for detail. For Easter 1235, Henry III had three sets of garments made: the first was of burnet, an expensive and dark (blue) fabric, trimmed with miniver (white fur); the second set was made of murray, a brown cloth, trimmed with vair; the third set was made of green cloth and trimmed with the grey and red spring fur of the northern squirrel.

Henry was one of the first kings to really acknowledge the significance of sartorial style in politics. When he was trying to persuade his barons to cough up funds to support his second son’s planned conquest of Sicily, Henry dressed the boy in a set of Sicilian coronation garments. The spectacle would have been doubly impressive as the meeting occurred in Westminster Abbey, which Henry was in the process of transforming.

Born in an era when women’s fashions were somewhat rigid, Anne (1902–92), who became the 6th Countess of Rosse in 1935, defied the prevailing norm, choosing to take her inspiration from history, and from the clothing of her ancestors.

Even as a young woman, Anne possessed an incredible awareness of history and narrative, preserving and wearing items of clothing that had been worn or collected by three generations of women before her. There was little financial value in many of the pieces of clothing she chose to preserve – many were past repair – but to Anne they held a poignant beauty of their own, evoking memories of family and providing tangible examples of lives lived. Each piece was carefully packed and stored in tissue, often with an accompanying note. One dress – by Jacqmar of London, decorated with purple glass beads – was stored with a handwritten note that read: “Had a wonderful time in this am ashamed to say. 1941!!” Anne was also proactive in creating her own look, using her needlework skills to embellish her clothing: virtually unheard of in the 1920s and 1930s.

Anne came from a family of famed collectors and gardeners, and this rich heritage provided inspiration for her clothes, with flowers – both fabric and real –featuring heavily in her designs. But Anne is more than just a fashion icon: she was an extraordinary woman, in any era, who regarded clothes as holders of memory and history, curating them for future generations in a very personal way.

As a prominent royal, Edward VII’s wife Alexandra (1844–1925) was acutely aware of her duty to dress appropriately, yet managed to influence British fashion, often without meaning to do so.

Alexandra was tall and slim in an age when a fuller figure was in vogue – the bodice of her wedding dress measured just 21.5 inches – but she dressed to suit her body type, eschewing bustles and fishtail trains and adopting a feminised version of the male suit, consisting of a tailored jacket and skirt. She brought this look into everyday fashion.

Another unintended look made popular by Alexandra was that of the choker necklace – usually worn with evening dresses – and high-necked blouses. Striking to look at, the queen’s choice of jewellery was, in fact, designed to disguise a scar on her neck, the result of a childhood illness.

Having examined a number of Alexandra’s dresses, I believe she may have suffered from a curvature of the spine – probably an indirect result of the rheumatic fever she suffered in 1867. Yet she avoided speculation about her health by making structural changes to her clothing. To have lived in the public eye for 60 years and successfully kept this disability from an increasingly sophisticated press demonstrates Alexandra’s sartorial eye. She may not have been a fashion leader, but she set trends that survive today.

Thanks to late 18th-century caricatures that portray him as fat, hirsute and unkempt, Whig politician Charles James Fox (1749–1806), known as ‘The Eyebrow’ to his friends, might seem like an unlikely fashion hero. However, he used clothes successfully and strategically to political ends, clearly understanding the power of clothing as a brand. As a young man he was a leader of the ‘macaronis’ – elegant young men identified by their adoption of flamboyant continental court fashions that included red-heeled shoes, expensive silk suits and elaborate lace frills.

But for Fox and his set, macaroni dress was more than a personal style. It was also a purposeful political statement intended to broadcast opposition to the government and English court through overtly European sartorial references, and the selection of foreign over home-made fabrics.

Fox continued to use fashion to further his political cause throughout his career. He left his wigs unpowdered to protest against William Pitt’s taxation policies (which included a tax on hair powder) and adopted the blue and buff colours of George Washington’s army as the colours of the opposition Whigs. His dishevelled appearance in later life was, it’s been argued, a premeditated statement of his claim to be a ‘Man of the People’, and his distance from the clean-cut William Pitt.

Long before Boris Johnson left his shirt untucked, or Tony Blair took off his tie, Charles James Fox understood, crafted and promoted fashion as a political tool.

Georgiana Cavendish, Duchess of Devonshire (1757–1806), was the most stylish British woman of the late 18th century and a fashion innovator in her own right. Dubbed the ‘Empress of Fashion’, Georgiana demonstrated her creativity and eye for style with many innovative creations. One of her most recognisable pieces was the ‘picture hat’ – a wide-brimmed, medium-crowned black hat not unlike the cavalier hats of the early 17th century. The hat sent the millinery world into a frenzy and women scrambled to have their own versions made.

But Georgiana was not afraid to shock. Indeed, she was probably the first English woman to wear the chemise a la reine, a dress of thin muslin, loosely draped around the body and belted around the waist with a sash. Resembling an undergarment, the style caused initial outrage in England and France, but soon became popular.

In much of her personal life Georgiana was powerless, trapped in an unhappy marriage, but in fashion she definitely reigned supreme.

Elizabeth I (1533–1603) stands out for the perfection with which she dressed throughout her long reign. A unique virgin ruler, she was not afraid of fashion and fantasy, but ingeniously drove its connection on. Hers was not a world of predictable cuts and monochromes, but of invention and allusion: one of her lace scarves was mischievously embroidered with a “hideous large black spider” on it, which frightened a foreigner “as if it were natural”.

Elizabeth’s attention to detail was both intricate and playful. She endlessly drew attention to her fine white hands by repeatedly pulling her gloves on and off.

Her whole attire was a perfect performance of gravity: even in her 60s, with an ageing face and rotten teeth, Elizabeth managed to mostly defy the misogynist conventions of the time, which dwelt so insistently on women’s physical decline. She would still look “gorgeously apparelled”, dignified and, in that sense, youthful in spirit.

Elizabeth was a queen of fine satins, emblematic embroidery, and loved to decorate her gowns with jewels and pearls (symbols of virginity). Novel features in her dress included ‘masculine’ jerkins, worn over doublets. But she was not wildly extravagant in her expenditure: in 1603, her entire wardrobe numbered 1,900 items. This might seem huge, yet it included every dress-related item she owned, down to single buttons.

The decade following the restoration of the monarchy in 1660 saw luxurious and novel fashions become a key feature of life at court. For me, diarist Samuel Pepys (1633-1703) exemplifies the Restoration courtier who valued fashion and spent large amounts of money on looking good.

We don’t automatically see Pepys as a fashion icon because we don’t have many paintings of him, but anyone reading his diary comes away with the sense that Pepys was, nonetheless, an avid follower of fashion, recording in detail the clothes that both he and his wife wear, as well as his fashion dilemmas: “…put on a summer suit this year; but it was not my fine one of flowered tabby vest, and coloured camelotte tunique, because it was too fine with the gold lace at the hands…”

Keeping up with social superiors was also important to Pepys. When he heard that the Duke of York was to adopt the 1660s fashion for periwigs (a decision that involved shaving off your natural hair), the dithering Pepys finally decided to take the plunge.

At times he even hired clothing to appear more fashionable: the brown ‘banyan’ gown (worn for receiving visitors) seen in the portrait that hangs in the National Portrait Gallery was borrowed for the occasion as it looked more expensive than his own version.

An English actress of the late 19th and early 20th centuries, Ellen Terry (1847–1928) brought the drama of the stage to her everyday apparel, favouring the rich colours, heavy fabrics and loose cuts that characterised the aesthetic movement of the late 19th century. Dubbed ‘The Cult of Beauty’, this was a movement that shaped the dress and decor of a certain set within society – by 1879, Terry was being hailed as its symbol.

But she was more than a fashion icon. Terry understood the powerful role that dress can play as a means of communicating the identity of the character she was impersonating on stage, yet recognised and exploited the fact that it was also possible to use dress as a vehicle through which to fashion her personal and public identity off stage.

One of Terry’s most iconic and memorable outfits was the ‘beetlewing dress’, which she wore as Lady Macbeth in 1888. It was crocheted from a bohemian yarn with strands of blue tinsel running through it, and covered with iridescent green beetlewings. Artist John Singer Sargent, who was in the audience for the play’s first night, apparently exclaimed, “My God!” when Terry first strode on stage in the dress, declaring that he had to paint her. More of a fashion rebel than a leader, Terry was an individual who appreciated and understood the art of dress.