After avoiding hats for many years and suffering through many cold winters as a result, I've finally decided to get serious about finding one that works for me. Reader "Pame9" recently reminded me of Eugenia Kim's chic and expansive collection (thanks Pame!) and now I'm a little obsessed with this houndstooth one. It satisfies all my criteria: I wanted a style that, aside from offering warmth, doesn't fit too snugly (to avoid hat head) and isn't too thick or woolly a knit (to minimize static cling). The checkered fabric, leather trim, and pared-down shape amount to a cool-but-refined take on an outdoorsy trapper—it's definitely cozy but still satisfyingly sleek, which was just what I wanted (but didn't think was possible) from a hat.

There's nothing more basic than a T-shirt dress—but this one from 3.1 Phillip Lim manages to be as understated as it ought to be and yet still feel incredibly special. The vibrant marigold is so unusual and appealing; it makes me think of India, which is especially welcome now that it's cold out. The cut is forgiving and loose though not baggy—it hangs just close enough to the body to flatter, and since it's made of ramie (a plant-derived cloth with a soft, silky finish) it drapes really well. But best of all is the keyhole slit in the back, which allows just a sliver of skin to peek through for an effect that's flirty but not too revealing. I like the way they've styled it with thick gray stockings in this photo (though I might go a shade darker with the tights for more contrast), and in the summer it'll look great with bare legs and flat strappy sandals.

In my fancy fantasy life, I'm the sort of person who never gets on a plane without this cashmere travel set. It includes suede-bottomed slippers, an eye mask, and an oversize wrap that doubles as a blanket. (Considering what a germaphobe I am, I'm shocked at how often I resort to using those scratchy polyester blankets every airline offers in flight—I mean, are those ever really washed?) I've seen the set in person and can attest to the nice weight and softness of the knit. As extravagant as it would be to have all those pieces done up in cashmere and wrapped in a silk pouch, at least they're legitimately useful, which helps justify their substantial price. And of course, there's a luxurious, jet-set aspect to the whole thing that's undeniably appealing too.

As stocking stuffers, I'm planning on getting these stationery sets from Sugar Paper in L.A. (one of the best places on the planet to buy paper goods) for everyone on my list. They come as a package of 10 letterpressed cards that have been stamped with a single black letter in a cool, subtly old-time-y font. They're classic, perfectly unisex, and at $20, amazingly well-priced.

At first glance Vena Cava's silk Birkin tank looks deceptively simple, but upon closer inspection there's actually a lot going on, and all of it's really good. The subtle, hand-drawn print includes several bands of barely-there tonal colors separated by delicate zigzags (do these remind anyone else of the readings off an EKG machine, or is that just me?), and the lemony trim at the neckline gives it an unexpected pop of brightness. The banded waist is classically feminine—not to mention always flattering—and the teeny buttons and two front pockets are fairly discreet while adding just the right amount of embellishment. Must, must, must have.

Apparently I'm in the mood for things that are a little wild: Yesterday I wanted a gilded computer; today I want a leopard top. And yet, like the computer, this blouse is just streamlined enough that it's actually quite easy to pull off. The neutral, black-and-white palette tempers the boldness of the animal motif, as does the clean, ladylike silhouette. It manages to be a bit sexy but still (actually, literally) buttoned up, and when paired with something as simple as tailored black pants, it's downright office appropriate. Who would have thought?

Lately—and rather strangely, considering I consider myself a fairly low-key kind of person—I love anything gilded. Things that are unexpectedly gold score extra points, and my very favorite product that falls into this weirdly specific subcategory is this iMac I stumbled on recently. It's insane, definitely, but in a good way: I guess I'd describe the overall effect as Versace flash meets Museum of Modern Art cool. And while the finish is (awesomely) over-the-top, the minimalist design of the computer actually makes it livable. If you already have an iMac, you can buy the gold casing on its own, as opposed to getting an entirely new desktop. While, at $600, the price for giving your monitor a glamorous face-lift isn't insignificant, at least it's a lot cheaper than a full-on tech upgrade. Or at least that's what I'm telling myself.

Though many a friend has tried to counsel me on how to stay warm through the winter, every year I feel as inadequately prepared as ever. It's my own fault, really. Despite the lectures I've gotten about the need for a proper knit hat (is it really true that nearly all your body heat escapes through your head?) and the merits of goose down and Thinsulate, I have yet to incorporate any into my wardrobe. This year, I have vowed to rectify the situation, and have been scouring the Web for cozy, cute, warm layers. And that's how I found these adorable, over-the-knee socks by Hansel From Basel. I plan on ordering multiples: They're perfect under pants for extra insulation, and I like the idea of showing a flash of color when I'm sitting down. Oh, and if anyone knows where to find a cozy woolly hat that still looks really chic, let me know.

I've said it before, but I think it bears repeating: If you find something that's versatile enough to use in two really distinct ways, grab it—there's nothing better than being able to rationalize a purchase on a cost-per-use basis alone. At least that's how I've managed to sell myself on this brilliant little bag by Jerome Dreyfuss. The French designer (he started in the business when he was still in his teens!) has crafted a tiny purse with a thin shoulder strap that's elegant enough to pass muster on occasions when I'd normally reach for a clutch. But the real appeal is that the strap slips off and the bag becomes a proper, ladylike wallet. Or jewelry pouch, or makeup bag, or whatever the occasion demands.

This is one of those pieces that really shouldn't work. Combining a hood and fleecy cotton material with a dramatic, billowy silhouette, it's sort of like someone turned a favorite oversize gym-class sweatshirt into a cape. It has big buttons that look like they were taken off of a ladylike coat from the '50s and zippered pockets that have a motorcycle-jacket feel. And yet the sum total is utterly alluring, with a utilitarian stylishness that I just love. Plus, I'm one of those people who likes to layer up, and the roomy cut and full draping sleeves will sleekly accommodate even my most elaborately piled-on outfits.

On my last trip to Chicago, I discovered Eskell, an incredible shop in Bucktown that's known for its feminine, retro-inspired house label. It's a good thing you don't need to visit in person to get your hands on the wares, because I'm totally smitten with this blouse. I love that it has a just-deep-enough keyhole front and rather sheer white fabric, so there's a nice, subtle, ladylike sexiness to it. It's a prime example of what makes the line so special: Though this is the kind of piece a really patient browser might find at a vintage store (or my resourceful fellow blogger Jennifer Romolini might turn up on eBay), it's also wholly modern and of-the-moment.

I like skinny jeans. I like how they fit, I like how they flatter, and I like how they feel; and so for what seems like months now that's all I've been wearing, and I haven't dreamed of buying anything else. Until, that is, this relaxed, wide-leg style from Genetic Denim caught my eye, and now I'm finally getting on board with the wide-leg trend that's been percolating through the Lucky offices. This pair is basically the inverse of the last jeans I bought: The color is classic, the rise is relatively high, and they're just distressed enough to look lovingly—and realistically—broken in. Best of all, though, is the leg, which is tailored and sharp but still wide enough to make me think that if Katharine Hepburn herself had ever deigned to wear jeans, these would have suited her nicely. And thus, they're good enough for me, too.

Right now I've got a special place in my heart for anything that smacks of weekends in the English countryside. These beautifully broken-in leather boots have equestrian-inspired touches (a buckle stirrup, a stacked heel) and would be perfect for wandering the misty grounds of some stately home in the Cotswolds. At the same time, though, they're versatile enough for use on the city streets, which, I'm afraid, are where my weekends are actually spent. They pair elegantly with a polished skirt-and-blazer ensemble yet are tough enough to just pull on and go with jeans and a big knit sweater. It's worth noting I found them on the finally-launched-at-long-last online home of Plum and Pear, two sister stores on the Lower East Side I've long loved.

A couple of months ago, throwing caution and practicality to the wind, I sprang for the most fantastic coat (from Gryphon New York, one of my very favorite lines) despite the fact that the style in question had three-quarter-length sleeves. It wouldn't be quite durable enough for our New York winters, I figured, but it would be exactly right for the cooler days of fall and spring. However, I just came across these incredible long gloves that are every bit as good as a sleeve. They're a wool-cashmere blend, so they're as warm as they are soft, and I feel so incredibly ladylike when I'm wearing gloves that extend past my elbow. And so I'll be wearing my spring and fall coat all winter long.

Accessorizing is one of those arts that are difficult to master (for some of us, at least—me included), which is why this cardigan from AKA New York is so brilliant—it comes complete with its own scarf and belt! The sweater itself is precisely the sort of basic you'd reach for all winter: It's a pretty but unassuming shade of heather gray, and would be a chicly minimal complement to either wool trousers or a colorful, fancy dress. But for me, the selling points are the long cashmere scarf, which looks great peeking out from under the cardigan but could be worn on any day, in any way, with anything, and the skinny leather belt, which gives the soft piece a bit of structure but can be removed if that's not the look you're going for.

It's tough to turn a boring task like lugging 20 pounds of dirty clothes to the Laundromat into something you look forward to. But this cotton laundry bag is going to make that chore (one I particularly dread) so much easier for me: Though it's sturdy canvas (as all such bags really ought to be), it's dressed up with soft cotton ruffles. It's like a big, flowing, found-at-the-flea-market peasant skirt repurposed as a utilitarian object, and it's a million times more attractive than most of the hampers/bags/baskets I'm used to seeing. I won't even mind leaving it sitting around the house until the next time laundry day rolls around.

There's a period between the end of daylight saving time and the post-Thanksgiving sales when getting dressed—at least here on the East Coast—is a nearly impossible task. Yes, it's cool outside, but hardly cold enough to justify breaking out a full-on winter coat. Hence, this puffy vest from the Italian label Add has become my newest crush object. Though it's stuffed with super-warm goose down, the silhouette is lean and fitted, so you look sleek instead of Michelin Man-ish. I also love the way the cashmere lining and slightly shimmering nylon dress up a piece that's so streetwise and utilitarian. Added bonus: The down is basically lighter than air, so this vest folds into almost nothing, which means you can easily cram it into a suitcase if you need to.

Whenever I want to justify a splurge, I tell myself: I can wear it in so, so many ways. I really can. And that is how I found myself typing in my credit card information and buying this M Missoni knit skirt. M Missoni is the lower-priced offshoot of the storied Italian knitwear house, and every piece it produces is just as ridiculously alluring as the stuff you see on the runway. This skirt's zigzag pattern and bold palette are signature Missoni, and the idea of a knit skirt is extra-appealing. Here's the real genius: You can wear this as a tube top as well. There you go: two pieces in one—it's a bargain!

There's a lot to be said for buying baby gifts. All those adorable clothes, sweet toys, soft blankets—they're always fun to give. But if you're one of those people who tie themselves in knots trying to be truly original (I am one of those people), baby gifts can be quite tricky. Which is why I think this mobile from Kiln Enamel is ideal: It's sweet enough for the nursery, sophisticated enough to appeal to any adult, and really unique. I prefer the multicolored version, with vibrant aqua and orange segments that are nicely offset by the sterling silver base. It reminds me of Alexander Calder. And it's so chic, no need to wait for a newborn—it would also make a great housewarming present.

Personally, I'd never have thought to put these three colors together, but I have to admit, there's something phenomenally good about the cream, chocolate brown, and mustard palette of this See by Chloé dress. Mixing hues is a delicate art, and sometimes logic doesn't apply—this somehow just works, and who knows why? And the shape of the dress is so timeless—with a fitted bodice and voluminous skirt—that it balances out the edgy colors.

Anyone who's ever shopped for a simple tee, or a standard cardigan, or an unfussy pair of pants knows just how hard it is to find a truly perfect basic. There are so many ways a seemingly straightforward piece can go wrong…which is why this tank fills me with a particular joy. It meets all my criteria: Made of sheer, super-soft jersey, it's cut long and lean, and it features this elastic Empire waistband that exaggerates the bust nicely. Just the kind of under-the-radar and versatile find that makes my heart soar. I know the model's pose is a bit vampy, but trust me—this tank's not as sexy and suggestive as the picture makes it seem.