The icon is normally upheld as the paragon of the period but this notion is made in hindsight. For in the time a personality’s legend develops, he or she is perceived as the product of her circumstances. This generally holds some truth for three generations of beauty, royalty and overexposure in the House of Grimaldi – from Philadelphia-belle-turned-Hollywood-star Grace Kelly to Monegasque Princess Caroline to millenium it-girl Charlotte Casiraghi.

Grace Kelly embodied the 1950’s stance of regal virtuousness; if the revelations of James Spada are to be taken as gospel truth, well, then she also captured its smoldering sense of sexual repression. Grace has been described as a contradiction of sorts (aren’t we all?) but I suppose hers stems from what was proper and what was taboo during her time. She might as well have been the feminine James Dean, in looks and in spirit.

Based on the biographies I read on Grace – most notably Spada’s down-and-dirty tell-all and her friend Judy Quine’s cloying semi-autobiography – she struck me as one who combined determination and charm to get what she wanted. As an actress, I thought Grace was rather bland but an eyeful to look at. Still, she had none of the spunk of Liz Taylor or the doe-like skittishness of Audrey Hepburn. As the years passed and she married and settled down in the Vegas of the Mediterranean, Grace seemed to be stuck in a rut. People have lauded her sense of fashion but even in that regard, Grace does not impress me. Her wedding dress was beautiful but that was the creation of Helen Rose. Grace’s dress on the day she met Rainier was one of the worst I have ever seen on anyone (and by any decade’s standards, except perhaps, the eighties).

Isabella Blow could carry the great headpieces Grace wore during the Red Cross Balls in the sixties and the seventies far better than Her Serene Highness. She did not impress me much as a mother (Jackie Onassis proved to be a better single parent than both Grace and Rainier) as her daughters proved too wild and her son too docile.

I would not want to live the life of Grace – one that was stuck in a limbo of sorts: between the stringent days of the fifties and the more libertine air of the sixties and the seventies. Underneath the charmed life she appeared to have led, I can only picture disillusionment and dissatisfaction. It would have pleased her to dabble in acting projects; this was denied her. It would have calmed her down to see her children settle down; this was not to be. It would have given her great joy to be a grandmother; this was not part of her job description. In the end, she snacked on too much caviar, gained weight and in all probability suffered from a stroke (while driving and most probably scolding her daughter, Stephanie). It was a far cry from the svelte young Princess, toting the Kelly bag named for her and sporting the chic wayfarers, with her portly husband and winsome children about her.

If Grace lived a charmed existence (at least, it looked good and glossed up on LIFE, Look and other picture magazines), her eldest daughter, HSH Princess Caroline, seemed to careen from one very public disaster to the next. Unlike the dainty mother, this willful girl possessed the sensuous looks of a Mediterranean beauty: fleshy and pouty. Caroline strikes me as rather intelligent; too intelligent, in fact, that she chafed under the narrow world of her mother. I think it was a failure on Grace’s part that she was not able to channel her daughter’s natural intelligence and talent properly. This may have accounted for Caroline’s restless spirit and quest for independence. Ironically, Caroline may have been technically virginal on her wedding night, which Grace was not (to borrow from the Gospel according to Spada). Grace had Hollywood lovers during the fifties but since Caroline came into age during the discotheque days, the latter was widely portrayed as the Lindsay of her day.

Little wonder that Caroline bloomed after Grace died and I don’t believe it is solely because she had no choice but to step into her mother’s shoes.

I think Caroline was more of an out-of-the-box-thinker than her mother was. She may have inherited that sense of self from Grace but the daughter knew her mind and was more confident of it. While Grace was placid in her beauty, Caroline exhibited verve and enthusiasm. She was stronger and more assertive, perhaps because she was to-the-manor-born whereas Grace was treated as an outsider in the early years of her marriage. Caroline also strikes me as a better mother, raising four children practically on her own. Last year, I saw a picture of Pierre giving his mother a hug after they lunched in New York. This seems to indicate a healthy relationship between mother and son. Andrea and Charlotte as well as Alexandra have been photographed being affectionate to their mother at an age when most stay away from their parents.

Now in her early fifties, Caroline may not have retained the dewy freshness of her looks but she appears to be more well-adjusted, more in control. She has come to terms with herself after a rocky marriage and a tragic widowhood; even as she faces the alleged flagrant infidelity of her husband, she works on what she can: raising their daughter and helping her brother in Monaco. I daresay she may feel more strongly about the pretty blond Charlene Wittstock becoming the principality’s Princess than an impending divorce (but that’s just me). I like Caroline; she is more real – the lady has made her mistakes (not the least of them, snagging her friend’s husband) but she has done what she could to improve herself and to do better deeds. Her fashion sense, though, seems to be on a regressive mode as she has turned up in some really questionable ensembles, most notably:

Caroline’s daughter, Charlotte, entered the worldwideweb’s collective consciousness in 2000 when she appeared with her uncle and younger brother at the Monaco Grand Prix – in a white blouse, black pants and shocking pink pashmina knotted around her neck. The effect was effortless chic and one had to remind oneself that Charlotte was then a month shy of her fourteenth birthday. She looked pretty mature then with her hair arranged in careful dishevelment and her make-up rather too thick. But she was gorgeous – Caroline with a hint of Grace.

Charlotte’s life may also embody certain elements in her mother’s and grandmother’s life. She lived in relative privacy but certainly was on the social map and calendar early on. She completed her studies while pursuing other interests, most notably horse-jumping shows. Charlotte is all doe-eyed innocence until one sees the almost lascivious curl of lip. She also isn’t afraid of public displays of affection: there’s a youtube video of her making out with current boyfriend Alex Dellal. When she was younger, there were pictures of her, scantily clad and sunbathing aboard a yacht. But Charlotte made sure she was all covered up and no stray nipple found its way out of her bikini top. Now, Monaco’s It-Girl is dabbling in journalism and has even taken up the issue of responsible consumerism. Which, in a way, strikes me as a ironic for one who shops and wears all the ultra-luxury brands out there. Apart from international fashion shows and equestrian events, there is little of Charlotte in the news. Which makes her a tantalizing fodder for photographers and cyberworld stalkers.

Above: this is the only really bad picture I have seen of Charlotte. Her hair is a wee bit put-out and her outfit makes her look like a skanktron. But, one bad picture as opposed to hundreds more which are just dazzling? Not a bad score at all:

I still maintain Charlotte is far more beautiful than her grandmother but I like the spunk that is in her mother – and which appears to have passed her by. This girl, though, has finally demonstrated that Grimaldis can dress well too!

And so in three generations of one family, one can trace a bit of history, a bit of pop culture… and a whole lot of gossip.