Wandering around the city lately, I've seen a couple of outfits so stunningly cool that I had to pretty much stalk the women wearing them for a block or two to get a better look. Both outfits were based around beautifully worn-in, low-heeled, brown lace-up granny boots—my newest I-never-knew-I-wanted-and-now-must-have-immediately thing. The first combination I saw consisted of skinny gray jeans, a plaid button-down, a big fringy scarf, and shoes that looked just like these. The second mixed a swingy little camel coat, a black minidress, extra-dark striped tights, and a slightly higher, more refined style like this pair. Both ensembles were interesting in a soft 80s-bohemian way, completely comfortable, and exactly the kind of thing I want to be wearing right now.

I've been on the hunt for the perfect gold hoops for years now. My ideal pair will loop all the way around (with an unobtrusive clasp) and are neither too big or too small, and definitely have to be real gold so they won't change color or turn the side of my jaw green (this has happened). Usually I find eBay's jewelry selection so exhaustive as to be overwhelming, but if you're conducting a precise search like "gold hoop earrings," the options become considerably manageable. Right now I'm pondering both this pretty, leaf-engraved version and this perfectly simple, rose gold pair. I can see wearing either in a dressed-up or more casual way, and at these prices, I won't feel terrible when the day inevitably comes where one magically disappears.

I feel excited every time I come across a listing from the excellent eBay boutique Hipster's Playground Vintage. There's something about the way the seller, a petite, elusive blonde, styles her clothes that's theatrical, siren-sexy, and so fabulous it makes me want to buy everything she posts. Not only are all of the pieces dry-cleaned or hand-washed and mended before a sale, she also consistently manages to source big-name vintage items, like this Dior skirt, that feel really modern. Right now, most of the inventory has a glamorous '80s theme, so you can find tons of sparkly dresses and evening jackets that would be perfect for holiday parties.

Nearly a decade ago, I stole—or rather, permanently borrowed—a boyfriend's striped V-neck sweater. It fit me perfectly and was one of those pieces in which I instantly saw endless fashion possibilities. I wore it for years: with boots and leggings, over a T-shirt with jeans and Converses, even to work with miniskirts and wedge heels.

That sweater is a distant moth-eaten memory, but I've been thinking about it lately and searching for a replacement. Both this A.P.C. style and this cashmere Vince version hark back to everything I loved about the ex's contraband, and with their slightly more grownup, feminine tailoring, they actually improve upon the original.

I stumbled upon eBay's hotel/travel lodging section last week when searching for luggage and was immediately intrigued and a little weirded out. Once I clicked through, however, I found that it's actually a staggeringly expansive, useful, and easily searchable service with good deals from a plethora of the countries you'd want to visit. It works like most other parts of eBay—there are auctions with or without reserve prices along with Buy it Now options. Also here is something called eBay classifieds, which are exactly what you'd expect: ads that link you to a person's website or phone number so you can buy the item directly from them. Some of the best listings are deep discounts on major resort vacations, but you can also find quieter, more modest trips. My interest was piqued by this private, oceanfront St. Thomas villa (the bidding on six nights starts at $100) and this sunny, one-bedroom apartment in the center of Florence (starts at $25 a night).

Note: Renting a vacation house on eBay might seem a little shady, but as with the rest of the site, there are lots of checks and balances so buyers feel secure. Also, most of these lodging sellers are certified through a company called Square Trade, which is kind of like an eBay Better Business Bureau, and has high customer service standards.

Like every other New Yorker I know, I don't have enough closet space. In fact, we have just one tiny closet in our entire apartment, which needs to store/hide the clothes and possessions of two adults, and it's woefully insufficient for the task. Because of this, I am constantly looking for creative storage solutions. This vintage '50s coat stand is one of the coolest things I've seen. It holds up to 10 coats (or really anything you want to use it for), comes with its original sturdy wood hangers, and has an excellent, sculptural appearance that's far more stylish than the standard metal clothing racks I've come across. Best of all, it's just 24 inches wide, which means it won't take up a lot of floor space, another element of New York living that's at an absolute premium.

Maybe it's the masculine/feminine interplay, or the crisp, looks-good-on-everyone cut, or the fact that they're fun to dress up and down—but I really love a good peacoat. You can find tons of bright, nipped-in takes by typing "pea coat" into the women's clothing finder (this sleek navy blue option is especially great; it reminds me of something a Bob Dylan girlfriend would've worn, circa Freewheelin'). But for a more substantial and classic version, search under "authentic pea coat" on eBay's main page, and you'll get the durable, military-issued, real deal. Just make sure to get your measurements right—from my calculations, a women's size 6 is about a men's 36R.

I have a theory that, with a bit of careful searching, you can find anything on eBay. Thrillingly, this theory is often proven true. For example, I'm going on a trip next week and this morning I woke up thinking, "I need a new suitcase." Specifically, I was looking for Filson's awesome leather-and-canvas rollie. It's a bag we featured in the magazine back in July and ever since I've been lusting after its rugged, slightly Amelia Earhart?ish quality. What I wasn't completely excited about was its $445 price tag. However, today on eBay, I found the same Filson piece, brand new, with tags, for just $289—even with shipping, I'll still save over $100.

Search tip: Travel gear is something I wouldn't necessarily want to buy used, but even on eBay, you don't have to. From the eBay home page, click on the Travel section. Once there, type in ?luggage? and you'll come to something called the Luggage Finder, a genius little search engine that allows you to choose the brand, style, color, and condition you're looking for.

Choosing a desk lamp on eBay is one of those shopping experiences that give me an identity crisis —there are literally hundreds to choose from, many of them are truly good, and most represent an entirely different style of living. Am I a Frank Lloyd Wright type? Do I want something classic and frilly? Am I the kind of person who pays a lot of money for something iconic and French? When all is said and done, I like things that are simple, inexpensive, and a little playful, so I'll probably bid on this vintage Hamilton style. It has a strong yet unassuming design and the sunny yellow color will brighten even my little, light-deprived home office.

I have a deep affection for patent leather. It reminds me of special occasions and my first-ever dress shoes (which were red patent leather Mary Janes that I scuffed immediately every time I put them on and that my ever-crafty mother painstakingly cleaned with nail polish remover before we got to my grandmother's—a trick I use to this day). I have a fancy event to attend in a couple of weeks and I've decided to only wear high-gloss accessories. I haven't found the shoes yet (hopefully black and strappy), but I have located a bunch of really excellent bag options on eBay, like this curvy, '40s-esque Judith Leiber purse. For something more minimal, there's a pristine, unadorned vintage version, and if I'm looking to splurge, this slim Gucci clutch really couldn't be more striking, or sexy.

One of the things that make the eBay shopping experience infinitely easier, more accessible, and just a lot more fun is finding a seller you love. Last month, I stumbled upon Twitch Vintage, an eBay store based in Clearwater, Florida, that's almost perfect. It's run by a woman named Robby, whose tastes lean toward the late-'70s and early-'80s—you can expect lots of feminine dresses and fun tops in bold patterns and slinky materials. I bought two pieces from Robby last week, this rust-colored prairie dress and the cutest Miranda July-esque ruffled blouse. Both items arrived in mere days, carefully wrapped in tissue paper, and exactly as described. Twitch Vintage may be my new eBay hero.

We are at last having autumn in New York, which is arguably the best time of the year to live here: The air is crisp, but not too cold; it's breezy, but not gusting. It's boots weather, jacket weather, and—best of all for us at Lucky—scarf weather. Big scarf/little dress has become a kind of uniform around our office, and, inspired by my co-workers' impressive choices, I have become consumed with finding the precisely right, will-elevate-any-outfit option for a while now.

This exotic shawl from the eBay importer Asian Cottage Arts really fits the bill: It's generously cut, with a bright pattern that's interesting but not too glaring. Plus, the bidding starts at less than a dollar, which means even with the substantial shipping cost ($28 to the US), it's a truly amazing deal.

Note: eBay photography can sometimes be confusing—even though this item is pinned like a poncho, the fine-print measurements show it's actually an extra-wide scarf.

There are some days, like today, when eBay and I somehow fail to inspire each other, and nothing I want is anywhere to be found. Instead of feeling defeated at times like these, I try my best to use my search powers for good by hunting for a specific item that someone I know has been unable to locate—whether it's over-the-knee boots or vintage schoolroom pull-down maps. Our senior fashion editor Laurie Trott has been dying for a serious, snug-fitting black leather motorcycle jacket. She especially wants one with soft leather and interesting details, like this style's unusual braided shoulders. Laurie sets the bar pretty high—so when she actually liked this one, I felt alive, thrilled, and renewed in my e-mission.

For some unknown reason, I passed on these very cute and ridiculously affordable fingerless gloves at the Marc Jacobs store last year. And by the time I realized my mistake and went back, they had completely sold out. I've been fixated on them ever since, considering all other gloves inferior, and even became, embarrassingly, a little jealous when I saw a friend wearing them last winter. Apparently someone out there had the exact opposite experience: snatching these gloves up and then never wearing them (the tag is still attached!). Their mistake, my good fortune: Now I can rectify this bad shopping choice. And, it turns out, if I want, buy one in every color.

There's an interesting fashion phenomenon I've noticed, and it's especially present here at Lucky: One day, a thing that you'd never thought of wearing before—maybe even that you swore you'd never wear—suddenly becomes something you must own right away. And maybe it's because the fashion girls are working on cute, sparkly holiday party stories, or because I saw a gold dress on Gossip Girl that was worn so ingeniously I wanted to rip the outfit off of the screen—but this is precisely what's happening to me with sequins.

For the past few days, I've been sorting through an array of glitzy tops, extra-tight skirts, and over-the-top glittering gowns; but what I really want is something more refined and simple like this black sequined minidress. It's sexy, but not too revealing, elegant, and reminds me of that amazing scene in Working Girl where post-makeover Melanie Griffith sashays into the party and effortlessly seduces Harrison Ford.

A few weeks ago, while riding to work on perhaps the most crowded subway car ever, I had an epiphany: my bag is too big. Though I love the security of carrying nearly everything I own in one misshapen, wider-than-my-body satchel, the truth is I bang into people, trip up waiters in restaurants, and suffer a permanent shoulder knot from toting 20 lbs around daily. It's time to streamline.

There are so many good, expensive-looking (but actually super-cheap) purses on eBay it boggles the mind. I found this clean, minimal, and slightly rustic vintage Coach messenger bag by typing in "saddle bag" and "brown" in the vintage accessories section. It's a thoughtful design—clean lines, basic colors, the bold button detail—so the bag feels substantial, even though it's much more reasonably sized than my current favorite.

We have big dreams around my apartment that someday we will live in an organized, well-appointed home filled with unique and comfortable furniture. As part of my neverending quest to replace the "I got this in college/the trash/my parents' basement" pieces that are still scattered about, I've been hunting for a beautiful, modern-looking rocker. This is not an easy task.

Type "rocking chair" into eBay and most of what comes up is either too Victorian-granny or too "Home Sweet Home" country-kitchen for my tastes. But this vintage plycraft chair is everything I've been looking for: sleek lines; a seemingly soft, cushiony seat; a bright, warm color; and not so midcentury that it's overly Jetsons-ish. Plus, it's (right now, at least) reasonably priced and located in North Carolina, not, say, England, so you won't get killed on shipping.

Search tip: I found out that eBay actually has a great, truly specific furniture finder. Once you're on the Antique Furniture page, there's a search bar on the left side of the screen that lets you look under the kind of piece (chair, dresser), the specific style (art deco, midcentury modern), and—if you want to pick something up—an item's location.

I started obsessing over these clingy, tailored wiggle dresses during the summer while watching the gorgeously curvy, red-lipstick-clad women of the AMC show Mad Men (which is based on Manhattan ad agencies of the early '60s and is so consistently smart and stylish that I hope it stays on the air forever). There's something truly old-school sexy about these pieces—they manage to be neat, elegant, and smoldering all at the same time, and you don't need to be a size 2 to pull them off. I imagine wearing one with a wide belt, sheer stockings, little heels and—if I were this kind of girl at all—a high-curled ponytail.

Is it wrong that I want a plaid shirt? I feel so conflicted. On the one hand, plaid, button-down shirts remind me of the best parts of the punk '80s, and I can't wait to wear one, untucked, with messy hair, skinny gray jeans, and little black ankle boots. On the other hand, they can sometimes bring back memories of the sloppy, grunge '90s, a period that I was unfortunately at the perfect age and income bracket to embrace. I think the key to getting a look that's more Debbie Harry than Eddie Vedder is to find styles that are slightly fitted and long enough so they just skim your hips. That, and I'll never again, no matter how convenient or devastatingly cool it may seem, tie one around my waist.

Search tip: I can hardly explain the 5,048 tops that came up when I typed "plaid shirt" into eBay. Narrow things down by first entering "women's vintage clothing." Once you're there, search for "plaid shirt" and you'll get an easily more manageable number (around 70) of options.

Every once and a while, I come upon a pair of shoes on eBay that fit me so perfectly, blend so seamlessly into my wardrobe, and get so many compliments that I feel like I was born to own them. This happened a few years ago when I won a pair of vintage Dexter stacked-heel boots for just $47. They were flawless right out of the box: an amazingly versatile earthy brown-burgundy color, with completely walkable heels, and somehow retro-looking but modern at the same time. I loved these boots.  I wore them with everything I owned and had them repaired three times until, eventually, they betrayed me with a large, unfixable hole in the left front toe.  I've been searching for a replacement pair ever since. If you find Dexter boots in your size, buy them. Immediately.

Most everyone who loves clothes has a designer they fetishize. For me, it's the late-'60s/early-'70s British designer Ossie Clark. I've been searching eBay for a piece by Clark for a while now, without much success—his designs are becoming more and more in demand, there are fewer to be found, and those that are available are often sold well above what I can afford (one dress was recently listed at $7,500). But the other issue I have is that while I love Clark's billowy floor-length chiffon gowns and drapey extra-wide-leg suits, I want something that I will actually wear a lot and enjoy. That's why I couldn't be happier to come across this short-sleeved wool cardigan. It's pretty and unique, it will look great with both skirts and jeans, and even from these pictures, I can see Clark's signature nipped-in, ultra-feminine tailoring. Most importantly, it's well-priced, which is what, in my opinion, an eBay experience is meant to be: discovering something you'd never be able to find elsewhere, at a price you can afford.