Prince Harry: Style icon or fashion disaster?

He cuts a dash in his ceremonial garb, but off duty the British royal is often unkempt. How does he get away with it? As the prince prepares to tour the US, Robb Young unpacks the royal closet.

One of the ways modern-day royals elevate themselves above the common celebrity is with a dose of pomp and pageantry. Castles and horse-drawn carriages work a treat but nothing says imperial mystique quite like ceremonial garb. For Britain's Prince Harry, a closet full of these costumes has a valuable added benefit:  it gives him the veneer of someone far more stylish than he really is.

From the royal wedding to the Diamond Jubilee, the past few years have provided plenty of opportunities for regal finery, and as an elite member of the British Armed Forces, Prince Harry was often resplendent in lavish military uniforms festooned with medals, brocade and epaulettes. Arguably, he cut a dashing figure. 

But the praise heaped upon him then and since has been disproportionate and sometimes histrionic.  Style arbiters at Britain's GQ catapulted him to number five on the magazine's 2011 “50 Best-Dressed Men in Britain” list – meaning his debut on the list ranked him above the likes of Jude Law and Mark Ronson.    

America's Vanity Fair magazine has even included him on its International Best-Dressed List in a photo feature of the prince wearing a host of uniforms under the tagline, "wolf whistle".  As well as showing Harry in his ceremonial military gear and army combat fatigues, the photo series presented the prince at a derby in a top hat and tails, wearing black-tie at a charity gala, in athletic kit for polo and other sports events, and dressed in two relaxed day looks for official appearances. Only one of the dozen outfits could be considered “off-duty”, a blue suit he wore for a film premiere. 

Strict protocol

What this highlighted was that the vast majority of Prince Harry's adult life has been spent either in a uniform or in an outfit dictated to him by a rigid dress code or royal protocol. Besides being counselled by advisors on what is and is not appropriate, there is inherently less room for error in the prince's sartorial affairs since, unlike women's fashion, menswear leaves little room for personal flair when it comes to formal engagements – often the colour and even the cut of the suit you are obliged to wear is prescribed. So how anyone – whether royal, famous, wealthy or all of the above – can be exalted as super-stylish when he has negligible free will in choosing the clothes he wears is a bit baffling. 

It is only through Harry’s sporadic private outings that we get a glimpse of his real personal style.  At its best, this consists of a rather nondescript jacket and jeans combination with open shirt and laid-back shoes such as moccasins, similar to the outfit he wore at last month's London marathon.  At his worst, Prince Harry morphs into a sloppy version of a preppy American college frat boy in scruffy baseball caps, threadbare T-shirt, cargo shorts and Birkenstock-like sandals.  Alternatively, there’s the baggy, boot-cut denim look with hooded fleece - as worn to several exclusive London night spots in recent months.  

But stylish or not, these looks make a statement. They reinforce the prince’s reputation as the mischievous member of the royal family – a fun-loving, well-meaning delinquent with the common touch, a potential loose cannon. And it is this impression of rakish charm and devil-may-care attitude that makes him one of the most popular international royals today. The message seems to be that, although he is gradually coming to terms with his responsibilities, and will eventually fulfil his duties with less scandal, he refuses to be seen as an uptight, upstanding member of the establishment on all but those occasions where it is unavoidable.  

Interestingly, Prince Harry seems to revel in those moments when clothes help him look the part of the charming buffoon or the loveable rogue. Cue the pink pinafore apron with cuddly Paddington Bear motif that he was given while cooking with children in Lesotho, or the oversized traditional shirt that he had been given as a gift and so wore at a Caribbean street party in Belize. On both occasions, the prince was positively beaming – a thoroughly good sport – and appeared endearingly at ease, unlike many other royals or celebrities who would find the obvious fashion faux pas an awkward or downright embarrassing photo op to endure.

Upper class code

Much like the popular illusion that he is a remarkably stylish young man, another media myth is that Prince Harry somehow embodies the spirit of a new breed of ‘Sloane Ranger’, or ‘Hooray Henry’ (a particular type of upper-class, Chelsea-dwelling Brit). True, there are occasions when he (or his advisors) get it right – for example, the beige linen suit and the much-hyped suede desert boots he wore on last year's Commonwealth tour. But generally speaking, Harry is too sloppy to be a Sloane role model. Britain's young upper crust today are well groomed, and although they might occasionally cultivate a deliberately dishevelled look, they would avoid looking thoroughly unkempt.

And unlike the prince, when an archetypal Sloane puts on one of his best suits, it often looks like it has been painstakingly made by hand at one of London's most luxurious tailors on Savile Row, even if it has not. Prince Harry's suits – most of which are in fact bespoke and made on the Row – sometimes flatter him but rarely look exquisite or all that expensive, even though they really are. For despite his royal pedigree and life of privilege, the prince lacks the gentlemanly elegance of his brother or the quaint propriety of his father needed to carry off such sartorial trappings in the same stately way. No, the suit doesn't always make the man. 

Left to his own devices, the prince would probably live happily for months from a single rucksack filled with nothing more than a ski anorak, boots, shabby jeans and whatever shirt his girlfriend packed for him. But it is his distaste for dressing up and his aversion to royal regalia that make Prince Harry all the more likeable and refreshing to so many of his onlookers. Somehow, he gets away with it. He seems more genuine because of it, and by consistently dressing down he earns an exemption from even the most avid style watcher’s scrutiny.  

If you would like to comment on this story or anything else you have seen on BBC Culture, head over to our Facebook page or message us on Twitter.