Allow Simon Doonan To Style Your Private Island Vacation. Because Dreams Are Free.

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Here at Racked, we're dedicating this week to the kind of fantastical shopping that most of us only get to experience in dreams (or at 80%-off sample sales, which are generally somewhat less than posh.) Taking a page from casino parlance, we'll be talking a lot about "whales," those big spenders who feel perfectly comfortable dropping tens of thousands of dollars every night on roulette, or, in our case, on Cartier. Welcome to Whale Week 2013.

When you're headed on another vacation of a lifetime but are stuck on what to pack in your Hermés suitcase, keep calm: Barneys' Ambassador-at-Large Simon Doonan is here to help. The window-display whisperer, accomplished writer, and skilled husband chooser has at least these two things in excess: Taste and luxury know-how. Both come in handy when planning a get-away to the ski-slopes of Saint Moritz, the beaches of Saint Tropez, and, naturally, that private island you own somewhere in the South Pacific. Read on for Simon's take on how to pack for a Whale Week vacay.

SAINT MORITZ

1. "Just because it's snowing does not mean you won't need an insanely sassy pair of pumps. A killer platform will keep your peepers out of the slush." Prada Peep Toe Studded Sandal, $1,100

2. "Every apres-ski girl needs a seriously groovy pair of shades. Enter the chalet and RULE!" Karen Walker Iris $280

3. "After a grueling day on the slopes and a boiling hot shower, you need to pamper yourself with a serious squirt of Frederic Malle." L'Eau D'Hiver, $150

4. "Do not even think about hitting the local club without a little quelque chose from the new YSL collection by Hedi Slimane. If the temperature plummets then wear your party frock over a unitard in a contrast color." Saint Laurent Baby Cat Tie Neck Mini Dress, $4,490

SAINT TROPEZ

1. "Think Isabelle Adjani in 'L'ete Meurtrier.' When shopping the flower and veggie market wear a flirty transparent tunic over your bikini." 3.1 Phillip Lim Beaded Tunic, $325

2. "Nothing screams Saint Tropez quite like a rustic, color-blocked hobo. Throw a book and a bottle of wine into it and head to the beach." Barney's Colorblock Hobo Bag $850

3. "It's little bit country, a little bit Vanessa Paradis. Yes, I am talking about a glamrock ankle boot. Perfect for schlepping up and down the cobbles." Marsell
Metallic Open Toe Ankle Boot, $895

4. "Think Brigitte Bardot (she still lives in Saint Tropez, non?). A nifty Isabelle Marant skinny pant can be worn with a cheesy vintage tee or a bohemian gypsy blouse." Isabel Marant Cooper Caprio, $290

YOUR PRIVATE ISLAND

1. "Yes, it's a private island, but that does not mean there will not be telephoto lenses pointing in your direction...therefore, you will need the best cut bikini. Paging Norma Kamali." Norma Kamali Halter Bra and Bill Bottoms, $350

2. "Every other gal will be wearing hippy sandals. All the more reason for you to kick it up a notch with a metallic pink Manolo." Manolo Blahnik Audi, $775

3. "Pack lightly. You do not need a ton of stuff when you are on a private island. See if you can stuff everything inside a sauvage ostrich clutch. The more sauvage the better." Deborah Barnet Sauvage Ostrich, $610

4. "Nobody can rob you on a private island, so festoon yourself with jewels by Irene Neuwirth." Irene Neuwirth Sapphire Pink Opal Diamond Drop Earrings, $22,380

· Whale Week 2013 [Racked]
· Simon Doonan Wishes He Never Bought Those Teeny Tiny Panties [Racked]