How do I keep the closet so organized? OCD comes to mind. It’s all very practical, though, with everything arranged by type and by color: jackets, tops, long sweaters, pants, skirts, dresses—how else can you find anything in the morning? All, Various Designers

I have a thing for the 20's, so when I saw this peacock feather headdress at the last Seventh on Sale—minutes before doors opened to the public–I knew it must be mine. My friend Lisa Airan swooped in and bought it for me as a gift (thanks, Lisa!). Frivolous as it is, I’ve worn it twice: once to a YSL masquerade party, and once to sit for a watercolor by the incredible fashion illustrator Bil Donovan.

This is a lightbox by the Chilean artist Alfredo Jaar. My mother represented Alfredo at her art gallery back in the eighties, and when she asked what I wanted for my Sweet Sixteen, I said: That. On top, a slim, ages-old white tote that I reserve for Riviera-type moments: You know, Capri, Palm Beach, the East Village. It’s very fancy-lady, but can be brought down to Earth with a pair of hole-y white jeans. Bag, CHANEL

This palest sage green is a color they doesn’t make anymore, and in fact, I had to beg for it. I waited a year and a half for this bag! I love icy colors, and I love them year-round—instead of winter-white, why not try winter-sage-green? I knew that for a bag this special, I wanted a shade I’d never see anywhere else. There is one place, though, where you can see this same leather: it’s what the walls are upholstered with in the elevator at the Madison Avenue store! Bag, Hermès

With this little red bear floating around in my bag, I never have trouble finding my keys. Keychain, Prada

These sandals are what you call an unintentional investment buy. I picked them up at the start of the studded moment (how many years ago was that?), and they just never went out of style. I think my office mates may be tired of seeing them by now. The sturdy, yet slim-looking heels are made for running after taxis. This custom-order ribbon and pearl necklace makes a simple black turtleneck look major. Sandals, Prada; Necklace, Custom 3.1 Phillip Lim

All-time favorite summer wedge. There is nothing these don’t look perfect with: dresses (strict to frilly), skirts (short to ankle-dusting), capri pants, palazzos, jeans… And they’re actually quite comfortable. Shoes, Christian Louboutin

This fur neck piece makes any coat instantly glamorous and deluxe. William Klein shot this picture for Vogue in the 1960s. Another gift from my mother, and one of my most treasured things. Bag, Vintage; Neck Piece, Giorgio Armani

Pearl collar bought in an antiques store in San Luis Obispo. Another wardrobe extender: It changes any neckline. Old-fashioned, ultra-feminine, of another era. J’adore. Collar, Vintage

My mother bought this necklace for me at the 26th Street flea market. It’s got a Grecian, yet very modern feel. Looks great with my grays, blacks, and pale pinks. Necklace, Vintage

Boots, Rag & Bone; Necklace, Marni

I adore dresses for work. It’s just so simple: zip it up the back, and, swoosh, done! This sleeveless one is more of a sculpture than a piece of clothing. It’s made of this beautiful stiff, yet soft, felt-y wool flannel. It’s like wearing a tulip. Dress, Yves Saint Laurent; L to R. Shoes, Shoes, Dior, Christian Louboutin

90's ponyskin: a keeper. Bag, Fendi

The best thing about CHANEL bags is that they get better with age. So my favorites here are the older and slightly beaten up ones: the burgundy camera bag with that great retro V-stitching, and the sort of nautical black with white trim—couldn’t you just see it dangling off Coco’s shoulder in Deauville? Bags, All CHANEL

A porcelain Jonathan Adler chipmunk happens to be holding up this crocheted wonder. I’ve been carrying this pretty consistently for a decade, and it never feels old. I’ve never seen another like it. This says summer weekend to me; it says vacation. It’s all good memories. Bag, CHANEL

Dress, Erdem

All, Various Designers

The designer gave me this incredible jacket some years ago, well before he was a CFDA/Vogue Fashion Fund finalist, and it always turns a million heads at the office. It fits like a bolero, and has these extra-long belled sleeves with slits up the sides. I always tell Gregory he looks just like Halston—the British version—but he never believes me. These boots were an impulse buy. How often does one see purple suede ankle boots? They’re good for sprucing up an all-black statement. I would not wear them with this jacket—feels a little too Carnivale. Jacket, Gregory Parkinson; Boots, Dior

These sweet pearls are equally great with a worn-in T-shirt or a prim dress. Jackie O, with a twist. Necklace, CHANEL

This clutch (the rare evening accessory which easily fits phone, keys, money, lipstick) is a staple. I have two others, one in turquoise snake, another in burgundy snake—but this is the one I wear most. Gold goes with everything (in my wardrobe at least), and this pale champagne shade just sort of shimmers. It has been to a lot of black ties. I love vintage evening bags. The embroidered one I found at a flea market somewhere downtown. It’s sweet and old-fashioned, but it looks just right with a modern day evening dress. The ivory leather bag I found in a consignment shop in Palm Springs. It’s a great shape and it cost seven dollars. Top to Bottom. Clutch, Lambertson Truex, Vintage, Vintage

This top—which feels like a sweatshirt, albeit one with silk navy leopard sleeves—is hanging on a piece by Jason Middlebrook in my living room. Again, my attempt to break out of gray/black/ivory and get into some color and print. I was shopping with my mother when I bought this—she got it, too. Shirt, Dries Van Noten; Shoes, Alexander Wang

Is there an editor in town that doesn’t have these booties? Is this why I made the Coveteur cut?! I love these in the summer with an amazing pedicure, and in the winter, too, with tights. They’re especially fun with a favorite red Prada shift. Shoes, Alexander Wang

I seem to buy the same bag each summer. Beyond the bag itself being perfection—shape, size, ability to haul around an extra pair of shoes— I thought these fabrics were really special. The striped linen is preppy, yet not, and works so well with summer neutrals. A portion of the proceeds from the navy ultrasuede with white leather piping went to a fund to save polar bears—who doesn’t love polar bears? Bags, All Balenciaga

I like anything that sparkles. I also like anything in the grey family. And I hate sleeves. Check! L to R. Dress, Marc Jacobs; Necklace, Vera Wang; Dress, 3.1 Phillip Lim

This frog’s name is Allin, named for the guy who sold him to me at a garden furniture store in Palm Springs. Allin wears a which I bought when we brought back Seventh on Sale. The necklace makes a cardigan and tank top look like a statement; it’s great with a conservative sheath; I loved it with a strapless black-and-gold Marchesa evening dress—but it clanks rather loudly whenever I walk down the hall, so, at work, I feel like a cat with a bell around its neck. Necklace, Gerard Yosca

Jacket, Alexander Wang; Shoes, Christian Louboutin

This white clutch looks fabulous here on my stove, and equally great with bright colors, or all-black (especially in the winter, when no one expects a white bag). It’s my ode to color-blocking, without the color. Clutch, Proenza Schouler

Tired of the ubiquitous stripe, I convinced the kind people at Goyard to create this stamp with my initials. I’d seen it on a piece of luggage, and thought it looked sort of Darjeeling Limited—! Not sure it’s a total success, but at least it’s different. I’ve been asking a good friend to paint a sprinkling of yellow stars on it, too. These hand-embroidered pillows are from the Moroccan shop in Chelsea Market. Bag, Goyard