If I Was A Rich Girl: True Classics

Well, yes, I am poor, and yes, this blog is dedicated to fashion that people can actually afford, but don't we all agree that part of the fun of fashion is fantasizing from time to time about the things we would buy if we were in possession of onyx American Express cards with infinite limits? Escapist, clearly, and ultimately disheartening, possibly, but fun nonetheless.

If I was a rich girl (and -- I implore you! -- take that as a reference to Fiddler on the Roof and not to that dreadful Gwen Stefani song by the same name), I can barely even guess what kind of fabulous fripperies I'd be flinging cash around on, but I can tell you what five iconic items I would have on hand in every color, incarnation, and sheen. Allow me to introduce you to (drumroll, if you please), my personal 5 True Classic Pieces.

1. The Ray-Ban Wayfarer

$139 at Macy's.

These seriously iconic sunglasses were launched in 1952 and even though they flit in and out of vogue (often with the help of whichever oft-photographed hipster ingenue has most recently stumbled upon them in her father's dresser), they will never go out of style. Need proof? Here is a truncated list of Wayfarer fans: Audrey Hepburn, John Lennon, Bob Dylan, James Dean, JFK, Roy Orbison, Andy Warhol, Debbie Harry, Anna Wintour, Elvis Costello, and of course the young Tom Cruise (pre-terrifying couch jumping and Scientology tirades, natch). Bret Easton Ellis name-dropped them in Less Than Zero, and Don Henley crooned about them in "The Boys Of Summer." In short, a woman in Wayfarers is a woman in excellent and stylish company. I'll take a pair in every color.

2. The Chanel Classic Flap Bag

Upwards of $2,500 at Chanel boutiques worldwide.

They say there are just two truly iconic handbags in this world, two that have withstood and will continue to withstand the test of time and trends. One is the Birkin. The other is, of course, the Chanel Classic Flap, also known as the 2.55. With apologies to Hermès (and I'm sure CEO Patrick Thomas is très, très désolé), when I'm a millionaire, my first big-ticket handbag will feature the interlocking C's. Born in 1955 and featuring the classic chain strap (at the time, a strap at all was innovative), the flap bag is absolutely timeless and has that singular magic that some high-end items posess, the kind that makes anything look effortlessly chic. Imagine this bag with a cocktail dress, and then imagine it with cutoff shorts and a wifebeater. Trust me -- it looks just as incredible both ways.

3. The Diane von Furstenberg Wrap Dress

Just one incarnation of DVF's wrap dress, $365 at Net-A-Porter.

Is there anything that flatters a woman more than a Diane von Furstenberg wrap dress? Does anyone have more of a way with fabric? Is there any dress more simple, chic, and stunning? I think not. When Diane von Furstenberg introduced her wrap dress in 1974, the fashion world took notice -- in fact, a green-and-white dotted version from '75 is part of the permanent collection at the Metropolitan Museum of Art -- and the style hasn't slowed since. When I am rich beyond my wildest dreams, I'd like to have a walk-in closet chock full of the goddess DVF's wrap dresses in every color, print, and style. Think about how easy it would be to get dressed -- just tie and look incredible.

4. The Louis Vuitton Monogram Canvas Luggage Collection

$460 - $6,850, at Louis Vuitton boutiques worldwide.

Going my way? If you've got this luggage in tow you certainly are. Now, normally I'm of the camp that finds items absolutely covered in logos a tad gauche, but you'd better believe that if I ever strike it rich, my travel accouterments will be the glaring exception to that little rule. Simply put, there's no chicer luggage than Louis Vuitton's classic monogram canvas collection -- for these exquisite suitcases, the LV to which I'm normally ambivalent just looks incredible. Even those notoriously rough-housing TWA guys at baggage claim will understand this is the luggage of a stylish creature and treat it with due respect. Have you ever seen a woman toting one of these puppies in an airport? That, my friends, is a fabulous, fabulous woman.

5. The Christian Louboutin Rolando Platform Pump

$700 at Neiman Marcus.

Feast your eyes, my sisters, on this, the holy grail of fashionistas and foot fetishists the world over: the Christian Louboutin Rolando platform pump. I don't know exactly what it is about Louboutins -- perhaps that cheeky red "follow me" sole, perhaps the towering height, perhaps the fact that every single pair is more gorgeous than the one before -- but I do know that this is the shoe that haunts my dreams. Friends, when I have a pair of these in my closet, I will know I have truly made it.


What about you? What do you consider to be true high-end classics? If you won the lottery tomorrow, what is the first piece you would buy?