Fantasy Dressing 

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What is it about the holidays that invokes equal parts generosity and greed? On one hand, there's a constant stream of gifting opportunities, helpful suggestions and the awareness that, yes, one is obligated to purchase cheery, festive presents for the top folks on one's list. On the other hand, there's Black Friday, the fresh-markdowns-induced frenzy of elbowing masses who—let's face facts—are most often shopping for themselves.

During one such frenzy, I spotted a woman carrying a bag I'd coveted for months but was unable to afford, and I was amazed at how instantly jealous and stymied I felt—none of which was exactly "holiday spirit" material. And so, in the spirit of that envious consternation that invariably nips at the heels of a season of wishful thinking, here are the moment's most coveted (and, for the most part, out of range) items. If you've got the cash (or you're paid in euros), this is without a doubt what you should spend it on.

A Tom Binns Necklace
Remember that stunning photo of Michelle Obama wearing a strapless gown and an over-the-top-yet-still-elegant pearl-and-sparkle necklace? Well, then you've got some idea of Mr. Binn's costume-y statement necklaces, which typically range from $500-$1,500. Go for colorful or estate-inspired—either way, you'll transform everything in your closet, from a black dress to a t-shirt and jeans.

Custom Earnest Sewn Jeans
If you're not already familiar with Earnest Sewn's brand of clean, sophisticated denim, I'd highly recommend taking a trip down to An Earnest Cut & Sew on Washington Street in the Meatpacking District. While rather expensive (most jeans run about $200), they're darn near perfect, in an elaborate range of bootcut-to-skinny silhouettes. However, it's impossible to find a pair that fits you just perfectly, so the store also offers custom pairs starting at $300. A pair of jeans that hugs your curves in all the right places, but also doesn't show your butt when you sit down? Priceless.

Eres Lingerie
Forget La Perla, Agent Provocateur and, for goodness sake, Victoria's Secret. The perfectly cut, wispy lace bras from Eres, rendered in feminine-but-not-girly shades of dusty rose, plum and pale gray, are the ultimate in sultry (but not overly sexy) underpinning. Frankly, it's a shame they're rarely visible. Especially since they're over $300.

Proenza Schouler's PS1 Handbag
It's hard to emphasize the "it" nature of this handbag. During Fashion Week, I started counting how many editors either carried one, stared at a friend's, or loudly discussed saving up for one. Possibly most importantly, in classic Proenza Schouler fashion, this is in no way an annoying-looking bag. With its part men's briefcase, part elegant lady's carryall vibe, it's kind of hard to imagine ever getting tired of it—especially in black leather or soft caramel suede. At this point, though, it's tough to find them, and even when you do, the price tag remains a stiff $1,595.

A Gary Graham Dress
Nominated for the CFDA/Vogue Fashion Fund Award this year, Gary Graham's moody, feminine pieces have become as sought-after as they are hard to track down. With layers of carefully piled lace and chiffon, or exquisitely patterned silks, the dresses manage to be confident, feminine and tough all at the same time. It's like only the coolest boutique in any given neighborhood is permitted to stock his wares, and once you finally lay eyes on (and invariably fall in love with) each finely wrought dress, you discover that detail has its price: usually around $800.

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