10 best dressed characters of all time

10.Vivien Ward, Pretty Woman

Thigh high, PVC boots held together with a safety-pin may not be everyone’s idea of sartorial elegance but Julia Robert’s tart with a heart’s style transformation as Vivien Ward in Pretty Woman is more than deserving of a place in our chart. From wig-wearing working girl to polka-dots at the polo, every outfit provokes almost unbearable envy. And let’s not forget that red dress, shoulder sweeping and finished with a sparkle of diamonds that truly indulged our Princess fantasies.

9.Holly Golightly, Breakfast at Tiffanys

From a present-day prostitute to elegant escort, Audrey Hepburn’s iconic turn as Holly Golightly has been admired for generations. Perfectly coiffed, even for prison, Holly’s bountiful beehive and shades that hide a multitude of sins have become a timeless trademark. The classic camel trench coat, simple black shift and string of pearls have become Hepburn’s legacy. She even looks good perched on the rusty fire escape, drainpipe jeans and Breton stripes almost making up for the terrible miming of Moonriver. All of which, of course, is accompanied by the ultimate in shabby chic accessories – Cat.

8. Carrie Bradshaw, Sex & The City

Whilst I would never advocate actually watching the film (that’s two hours of my life I will never get back!) there’s no denying that Patricia Field’s styling matched with SJP’s expert eye makes for a veritable feast of fashion. Ignore the shallow storylines and focus on what’s really important – the dresses. That wedding dress, a Vivienne Westwood masterpiece was so stunning that it survived potential ruin by the addition of an inexplicable bird in Carrie’s hair and Bradshaw’s androgynous ape of Annie Hall, pink pinstripes, white waistcoat and tailored trousers is equally excellent. Finished, of course, by a pair of diamond Manolos; worth marrying the balding Mr. Big for!

7.Annie Hall, Annie Hall

Woody Allen’s rambling may not be for everyone (I personally love a good witty rant) but Diane Keaton’s marvelously masculine sense of style is a breath of fresh air. Sex appeal may be subtle, very very subtle, but this directional dressing suits Annie’s no-nonsense attitude perfectly. Palazzo pants coupled with crisp white shirts and ties make Annie stand out without resorting to the usual cleavage-exposing male fantasies normally inflicted upon leading love interests. This was power dressing before the shoulder pads came and knocked everyone into submission, sleek, sharp and making a statement, we can all say a word of thanks to Woody as we slip into our beloved brogues this Spring/Summer.

6. Coco Chanel, Coco Before Chanel

In a film depicting the early career of the Queen of chic Ms. Chanel it is perhaps a tad predictable that Coco makes our top 10 list but it is an accolade rightly deserved. Audrey Tatou, who, let’s face it, could make a paper bag look good bravely battles through in the face of an unloved bob and some seriously dodgy eyebrows and manages to make fisherman’s garb a garment to envy.

5. Andie Walsh, Pretty in Pink

Grab your sewing box and put your amateur dressmaking skills into action after a viewing of John Hughes print-tastic Pretty in Pink. Proving the 80s isn’t all puffball prom dresses and nasty neon, Andie’s attention to detail is second to none with delicate lace collars, statement hats and a commitment to the chintziest florals ever made. Honourable mention to Ducky, the brothel creepers, sharp suits and slicked D.A. make him miles above dreamy but dull Andrew McCarthy in the sartorial stakes.

4. Neo, The Matrix

Whilst it has more than a slight nod to a seedy S&M fantasy, leather clad Neo has found a look that works and sticks to it. Hidden behind the obligatory superstar shades, Keanu sticks with the old adage that black never goes out of style whilst rocking the savage shaved head and perfectly coiffed crop with equal aplomb. Heavy duty biker boots and a statement full-length coat add an underground edge to our cool crusader, all the more necessary when you’re acting opposite Miss Whiplash.

3. Summer Finn, (500) Days of Summer

The ultimate indie girl Zooey Deschanel perfects jumble sale chic without veering into vintage granny. Summer glides through the office and into our hearts in her fifties sun dresses, A-line skirts and pretty button-up blouses. Pretty pastels reign teamed with cute hair bands and high hair prove she is far out of Joseph Gordon Levitt’s league in the style stakes (sweater vests are never a good look Joe, never.) All in all, a wardrobe well worth obsessing over.

2. James Bond, any James Bond film ever

Although some of his incarnations have been more successful than others – George Lazenby why, just why – one thing endures; 007’s enviable sense of style. With a sharp suit pressed to perfection whatever the latest life-endangering situation, Bond moves from cocktail bar to enemy lair with ease. And for the more shallow minded, few men look as good in their trunks as Daniel Craig, a licence to thrill indeed.

1. Jim Stark, Rebel Without a Cause

James Dean captured the spirit of a generation in Rebel and his style is still influencing fashion sixty years later. Turned up blue jeans and scruffy converse topped with a simple white tee and red bomber give Jimmy the edge in the style stakes. Simple but timeless, especially when accessorized with a rock n roll, devil may care attitude.

By Verity Hogan

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