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WE MIGHT AS WELL START, JUST TO work the kinks out, by going dress shopping with my wife. Now, if you’re a man reading this, it’s a safe bet that you’re not thrilled about the prospect of going dress shopping with my wife, much less with your own wife, or going shopping for much of anything save for handheld electronics or a massive, high-definition video monitor. Chances are, if you’re a man reading this, you’re a grab-and-go sort of chap when shopping by yourself, or a wait-and-whiner when shopping with your wife. Either way, you’re not likely to be wild about coming along on this foray. Grab-and-goers and wait-and-whiners have been subjected to serious academic scrutiny. I’ve looked at some of those studies, but they haven’t told me much beyond what I already know. If you’re a typical grab-and-goer, your overriding mission is to get into and out of stores quickly and stealthily. If you’re a wait-and-whiner, you’re crabby and impatient. You sit sullenly on a backless bench (if you can find a bench) while your partner picks over merchandise or tries things on, interminably. For now, if you’re that kind of dude, hang in there. This first expedition won’t take very long. And, happily, you can come along without leaving the comfort of your La-Z-Boy, with a caipirinha to keep you chill.

The reason for the dress-shopping trip was, on the surface, straightforward: Linda needed—maybe just wanted, the distinction gets tricky, as I’ve already mentioned—a little black dress. The occasion was the forthcoming annual fund-raiser at our kids’ high school. It happens every spring. The school draws up a shopping list of goodies not easily obtained through its annual operating budget: electronic SMART boards for classrooms, new computers for the library. The agenda is always the same: parents arrive and stand around chatting. Drinks are passed, lubrication for the main event, a Dutch auction. Besotted, we file into the auditorium, where we watch an upbeat video that depicts the school’s students acting in ways they never do at home. The video portrays them bright-eyed and alert, paying rapt attention to teachers, not shirking assignments or zonked out on video games. They race across playing fields with joyful enthusiasm, not chewing Oreos with their mouths open and bingeing on Red Bull, as they do in the basement. The video is a well-wrought infomercial calculated to persuade parents that our kids are flowering, not floundering. When the video finally ends, there’s lots of clapping, and then a professional auctioneer takes the stage to adroitly work the crowd. When the bidding sinks to a donation level you can live with—i.e., live with now that you’re a little tipsy and worth a lot less than you once were—you raise your numbered paddle, a volunteer records your pledge, and that’s it, save for a high-spirited raffle—two tickets to a Bears game! Then everyone files out for dinner and chitchat with other parents and teachers. Drink enough wine and the evening, while costly, turns out to be more festive than it sounds.

The invitation, in keeping with the tradition that this was no ordinary fundraiser, but a “gala” fund-raiser, calls for “cocktail attire,” meaning that men are expected to wear business suits and women, well, cocktail dresses, that is, not long dresses with beads and excessive froufrou, just classy dresses, usually but not necessarily black. When the invitation arrived, Linda mentioned something about having worn the same thing to the past two fund-raisers and that she “wouldn’t mind” looking for a new little black dress for the upcoming occasion. Now, normally she would just go off on her own and look for something like this, leaving me at home to fiddle around online. But given that I was beginning research on a book about why and how people buy, I asked whether I could tag along with her, an embedded reporter. There’s a catch, I said. If I go, the reader goes, too. Linda was fine with that, or so she said. Deep down I knew she wasn’t wild about having me—let alone you—play peeping Tom as she slipped in and out of dresses in a cramped changing room. I don’t imagine this is anyone’s idea of a pleasant shopping experience, not that shopping experiences are always pleasant to begin with, whether you travel solo or in a platoon of friends or total strangers.

We started out walking south on Michigan Avenue. Hundreds of shops line the Magnificent Mile, large and small, cheap and expensive, freestanding and tucked away in vertical malls, the majority in business to sell clothes and accessories to women. I intend to revisit the Mile quite a few times before this story ends, assessing stores that sell everything from American Girl dolls to Harley-Davidson dog collars. But for now the plan was strictly to look around for a little black dress at one of the Mile’s large department stores. Why a department store? Linda is a pragmatic shopper. She knows, every woman knows, that department stores offer a generous selection of dresses at a suitable range of prices, and there are always—especially in crummy economic times—things on sale. Department stores practice what the trade refers to as Hi-Lo pricing, meaning that merchandise is initially marked up so it can be methodically marked down to give customers the idea that they’re getting a deal. Because the Hi-Lo game has been played for so long, most of us are trained almost never to buy anything that isn’t on sale. You know it and I know it: the Hi-Lo game is something of a scam, yet we fall for it again and again.

Our first stop was to be Bloomingdale’s. But on the way there we passed a run of ultrachic designer boutiques. Impetuously, we stopped in at Chanel, if only to see how the fabled French fashion house defined that season’s edition of the little black dress. At the front of the shop, where merchants display what they deem to be “impulse buys,” we encountered a rack of Chanel sunglasses—more precisely, and especially at these prices, Chanel eyewear. Each pair sat in its own elegant Lucite cubby, dozens of cubbies in all. Between the columns of cubbies, in elegant typography (lest anyone forget she is looking at eyewear in a store called CHANEL, not Lane Bryant):

The repetition of CHANEL CHANEL CHANEL reminds us how the concept of product branding came to be: a red-hot iron searing (so as never to fade from living memory) a mark of possession into an animal’s hindquarters.

Duly singed, we browsed the generous selection of eyewear styles, many in the form of immense, wraparound tortoiseshell frames with none-too-modest overlapping Cs anchored to the temples. (The iconic Cs were designed by CC herself, back in the midtwenties.) I gathered that on some of those frames the Cs were crafted in real leather, a level of detail that comes at a price: Chanel sunglasses cost $350 and up, a rather expensive impulse buy by any reasonable standard. But relative to other impulses that might grip us on a rainy-day lunch break or a Saturday afternoon when we need a mood lift, $350 is not an unreasonable price tag—assuming we’re well enough fixed to buy our antidepressants at Chanel. At Chanel, $350 doesn’t buy much more than what you’ll find near the front door. Venture deeper into the shop and you’ll encounter spirit-enhancing Chanel shoes that start at around $500; chase-the-blues-away handbags at $1,000 and up. Of course, the savvy shopper knows that Chanel knockoffs—sunglasses and handbags mainly—are available at considerably less cost on street corners in most major cities, assuming one is willing and able to live with Not The Real Thing. Asian shoppers, for example, are notoriously designer-brand fixated and demand the Real Thing. It’s commonly reported that over 90 percent of Japanese women own something Louis Vuitton, having spent on average $247 per handbag. A great many teenagers also crave the Real Thing, though only teens in certain ZIP codes have any interest in, or can afford, Chanel. But even teenagers who live beyond Scarsdale, Greenwich, Lake Forest, or Beverly Hills happily pay a premium for the Real Thing, if the Real Thing is North Face, Juicy Couture, or Rugby, among other brands that, at any given trend nanosecond, impart a necessary je ne sais quois to the self-expression their hormones are aching for.

We arrived at Bloomingdale’s on this chilly weekday only to find the store so empty you could shoot off a cannon without hitting anybody, as my father used to say. Department stores are facing stiff challenges in an age when buyers prefer to shop in specialty stores, spectacular flagship stores, and big-box discounters. Stepping off the escalator, I (we) followed my wife across the empty sales floor to a far wall, where a thicket of little black dresses clustered. They carried labels—ABS, Bianca Nero, Kay Unger, David Meister, Laundry by Shelli Segal, Chetta B—that meant nothing to me and not much more to Linda. Maybe some were private labels masquerading as “real” brands, maybe not, who knows any more? Department stores are hell-bent on rolling out their own labels, because there’s more profit to be made by cutting out the big-name middlemen and women—Ralph, Liz, Donna, Ermenegildo, and the rest. At JCPenney, for example, about half the chain’s apparel sales derive from exclusive Penney lines: Arizona, Worthington, a.n.a., and so on. At Macy’s and similar department stores, private-label sales have been increasing three times faster than sales of tried-and-true brands. In 2007, Macy’s made Tommy Hilfiger a “strategic alliance” offer he couldn’t refuse. Hilfiger agreed to sell his signature line exclusively at Macy’s, in effect making Tommy a semiprivate label. New and instantly recognizable private labels are launched routinely in today’s marketplace. Many carry the signatures of celebrity endorsers who have little hands-on involvement with design: Madonna’s line at H&M on the lower end, Kate Moss’s at Barney’s New York on the upper—that is, before Kate went on to bigger things at Topshop.

Linda began to work her way through the acres of chrome racks, rattling hangers as she went, lingering a bit longer near dresses on racks with little SALE signs attached. The signs promised a further reduction of 25 percent should one of the dresses make it through the decision-making process and wind up at the cash register. Keeping a safe distance, I watched as Linda sifted through the lot, feeling fabrics with a thumb and forefinger to determine whether they have what the trade calls a “good hand.” There was something a bit melancholy about those dresses on sale: wallflowers at the orgy, they seemed to me. Buyers had passed on them for whatever reason: bad lines, a bad “hand,” or perhaps a bad Bloomie’s buyer had simply bought too many of them. Out of compassion for the on-sale dresses, but also out of hope that we could save a few bucks, I secretly rooted for Linda to find a dress here worthy of marriage. A man for you, right? In any case, fifteen minutes of hanger rattling yielded results: a quartet of little black dresses, all priced between $200 and $300. Linda handed them over to a saleswoman who ushered us into a changing room, where we locked ourselves in.

Changing rooms can be grim, as everyone knows. A survey reports that seven out of ten shoppers want changing rooms to be big enough to accommodate two people; seven out of ten want to be left alone in the room, whatever its size, with no salesperson hovering outside. The changing room at Bloomingdale’s seemed to have been spruced up recently. There was an enormous mirror, squeaky clean, and a comfortable leatherette bench for me (you, too) to slouch on as my wife slipped out of her street clothes and prepared to try on the four little black dresses lucky enough to have made it to the quarterfinals. Each seemed to be waiting, dying, to be the one asked to the cash wrap, then on to the gala.

For a lot of shoppers, particularly male shoppers, to get out of your clothes, try something on, take it off, try something else on, take it off, and so on until it’s time to put your own clothes back on, is one of life’s—that is, life in a consumer society’s—most dreaded rituals. Many women, too, have told me they hate trying on clothes; others, not so much. Linda doesn’t seem to mind, even with onlookers present. Those who dislike trying on clothes give several reasons for their dyspepsia. One: cramped, usually dingy, quarters. Two: you’re not really sure what looks good on you to begin with—does it make my ass look big? Three: the dressing room feels like an isolation booth, just you and your insecurities trapped in a small space. Four: you’re usually conflicted about spending money on whatever it is you’re trying on. Five: there’s all too often the annoying presence of the dreaded hoverer, who keeps coming to the door, calling out questions presumably meant to be helpful but that in fact rush the decision-making process and apply even more pressure:

“How ya doin’ in there?”

“Everything OK in there?”

“Can I bring ya anything else in there?”

“How’s it goin’ in there?”

Linda shimmied into the first dress (the label read Laundry), zipped up the back, and with narrowed eyes took a good hard look in the mirror. Though no expert, I’d say the technical term for what she had on was “corseted”; that is, rather tight around the midsection and calculated to amplify what in my wife’s grandmother’s time was referred to as a “bosom.” After staring at her reflection for a minute or two, turning left, turning right, checking out her legs, shoulders, and accentuated bosom, Linda rendered her verdict:

“I look like a dominatrix.”

Quick color commentary: this much I know from personal experience—there’s more going on here than meets the eye. Settling on a dress, a necktie, a pair of high heels or athletic shoes, is complicated business. The decision to buy has to do with far more than “I like it/I don’t like it.” Many of the things we decide to purchase—clothes for sure, but also home furnishings, cars, kitchen appliances—must surmount hurdles far beyond those relating to a product’s practicality or, sad to say, its objective “value.” The decision to buy something like a dress is a kind of puzzle. Multiple pieces need to fall into place before we, as buyers, cough up a yes. If a potential purchase crashes into one of the hurdles, or various puzzle pieces fail to fall into place, the Buy is rejected. In the case of dress number 1, which now lay rumpled on the floor, Linda decided it flunked the Appropriateness Test. You don’t go to a fund-raiser at your kids’ school dressed as if you are panting to take a riding crop to the headmaster.

Okay, back to the action—dress number 2.

This time my wife didn’t step into it, she pulled it over her head (which, come to think of it, is another reason to hate trying on clothes: it messes up your hair). Until that moment, I’d never thought about why women sometimes step into dresses, while at other times they pull them on over their heads. I suspect many other men haven’t thought about it either. But watch people shop, you learn things. If a dress has a zipper on the side, a woman pulls it over her head. If the zipper’s in the back, she steps into it. The dress my wife was pulling on now, by Chetta B, was one she’d especially liked while rifling through the racks. One tiny problem; the store didn’t have it in her size—Linda generally wears a 6, this was a 4. But she elected to try it on anyway because, as every woman knows, size matters, though not very much to clothing manufacturers, for whom “size” is fairly arbitrary. I happen to know this because when I worked at Lands’ End I often heard merchants talk about how one label’s 2 is another label’s 6. Part of this has to do with shrewd marketing strategy: let ’em eat cake, but if you want to sell ’em clothes, trick ’em into thinking that the cake they eat doesn’t put on pounds. The trade term for the ruse is “vanity sizing,” which flatters customers into believing they’re more svelte than they really are. The deception occurs worldwide, and authorities abroad are acting. In 2007 the Spanish government declared war on vanity sizing, decreeing that female store mannequins be draped in size 10 or larger. As far as I know, no such trailblazing legislation is pending in our own nation’s capital, even though, according to an industry trade magazine, more than one out of two female shoppers in this country say they have a problem finding clothes that fit, with inconsistent sizing a prime reason. Over 40 percent say the sizes of clothes in their closets range widely, and nearly 20 percent say they have items they’ve never worn because they never bothered to have them altered.

In this case Linda elected to try on the dress anyway, because if she really loved how she looked in it, she could ask the store to order another in the next size up. Well, it turned out that the 4 was too small, but that’s not what scotched the deal. What scotched it was that this little black dress had made a much better impression when worn by a cheap plastic hanger than by a living human being. The dress had, as Linda put it, “way too much going on”—waves of pleats running up and down the dress from the neck through the bosom, all the way to the hem. In other words, the dress had failed to clear the Aesthetics Hurdle.

Dress 3 was by Vera Wang, whose bridal shop on Madison Avenue has for years been where the affianced rich, or those who strive to be, order their wedding gowns and dresses for bridesmaids. But like just about every other luxury brand—Chanel, Gucci, Vuitton, Armani, and so on—Wang has over the past several years elected to go wide (not mass, darling, wide, or in Vera’s case double wide) by expanding her product line in every conceivable direction. These days, buyers aren’t so much fashion victims as brand victims. Or, more precisely, brand-cum-lifestyle victims—a brand such as Vera Wang isn’t just about luxury, it’s about a way of life. Result: if you’re into Wang, bring on the Wang. A Vera Wang brand victim can now slip her painted toes into Vera Wang footwear, hide behind Vera Wang eyewear, sparkle in Vera Wang fine jewelry, spray Vera Wang fragrance behind her ears and under her breasts, write thank-you notes on Vera Wang fine papers, set out Vera Wang china and stemware when she entertains, even slumber on a Vera Wang mattress, which, however ludicrous a Vera Wang mattress might sound, is perhaps the most logical brand extension of all. Wear Vera Wang on your wedding day, sleep on Vera Wang that night (and, should you be so lucky, through the many years of blissful nights that follow). And now there’s also SimplyVera, a low-price Vera Wang line that is to Kohl’s what Martha Stewart Everyday was to Kmart: a Faustian brand-extension risk.

The (not Simply) Vera Wang dress Linda had by now slipped on bore little connection to a wedding day or night, save for a subtle hint of same: a couple of cream-colored buttons on the front, covered in fabric—brocade? Jacquard? Turkish taffeta? what do I know?—one associates with a wedding dress. I couldn’t help but see those buttons, however, as anything but two wide-open eyes staring out from just below the bosom. I stared at them, they stared back. They unsettled me but didn’t seem to bother Linda, probably because she couldn’t make eye contact with them except in the mirror. After considerable reflection, Linda judged the dress to be simple and tasteful, “kind of cute,” she said, a phrase women shoppers commonly murmur when they run across something they are, in fact, wild about. When Linda asked me what I thought of the dress, I hesitated for a moment. I’d resolved to be as invisible as possible throughout this expedition, a fly on the dressing room wall, better to observe things as they really happened without influencing the eventual buying decision. But discipline failed. I told Linda I didn’t honestly think the shape of the dress was all that flattering, and hard as I tried, I couldn’t take my eyes off the buttons that kept staring at me. So I told her so. That comment was, sorry to say, sufficient to kill the deal. The moments also illuminates yet another Buy hurdle: doubt—a reservation planted by a husband, a wife, or some other companion along for the ride.

(Hang in there, guys; we’re almost finished.)

The fourth dressed turned out to be made by the same designer who gave us the dominatrix dress, only this one, in the words of my wife, was “flapperish”: a dress to Charleston in, not that anyone does the Charleston anymore, not even at bar mitzvah parties. After turning left, turning right, walking to the mirror, then back to her original spot, Linda uttered the magic words—“but it’s also kind of cute.” It was also kind of—no, not kind of, incredibly—wrinkled. No one had bothered to give the dress even a cursory steaming when it was unpacked it from the shipping carton that carried it on its journey from a village in China, where it had—no surprise—been sewn together. But even wrinkled, the dress was cute, I had to admit. The skirt was short, just above the knee, a plus given that Linda has really nice legs. The dress came across as playful and kicky. Linda thought so, too, but therein was buried the seed of yet another potential reason to reject: the Projection of Self Hurdle. “I think it might be too young for me,” she said, all the while examining the dress from every angle. Buying clothes gets especially tricky when you reach middle age, Linda remarks all the time. A woman of a certain age doesn’t want to buy things that make her look frumpy, but she also doesn’t want to buy things that make her look like she’s trying to pass for a chick three decades younger or, just as bad, a bar-hopping cougar on the prowl. There’s nothing less appealing than that, Linda says. But I could tell she truly liked herself in that particular little black dress, which is doubtless why she spent so much time in it, noting that she generally appreciates how she looks in a flared skirt, and that the dress would be knockout worn with black tights and slingbacks. Then—threateningly—the Age Cloud passed over again.

“Tell the truth, is it too young for me?”

“No,” I said, by now dying to get the hell out of there. “I think you look really great in that dress. Young, but not too young. Not a hottie, no way.”

After further reflection, Linda decided to buy the dress. And—cue the brass section—the chosen one turned out to be on sale! We had made it across all the hurdles, and my wife now had a new little black dress to wear to the gala fund-raiser. For those of us keeping score:

Price tag: $290

(Less) Hi-Lo discount (20%): $58

(Plus) Illinois sales tax: $20.88

(Bottom line) VISA charge: $252.88

Total time spent looking to buy little black dress: 1 hour, 45 minutes

The excursion now in the bag, what are we to make of it?

Bluenoses out there—anticonsumerist Buy Scolds—would argue that dark forces conned my wife into thinking she needed a new little black dress in the first place. They’d point a damning finger at slick advertising carried in fashion magazines that, in fairness to the Scolds, Linda sometimes reads. More generally, Buy Scolds rail at the bloated, superficial culture that seduces women into thinking that it’s what’s on the outside, not the inside, that counts.

Others who comment on reasons we buy say that even if my wife wasn’t exactly manipulated into purchasing the little black dress, she was conditioned by decades of media images. Armani suits, you’ll recall, registered on men’s radar with the release of American Gigolo, starring the impeccably Armani-clad Richard Gere. As for the little black dress, movies and fashion retrospectives have relentlessly promoted it as an iconic wardrobe staple, a must-have. Credit belongs to Coco Chanel, who presented us with the LBD long before her trademarked interlocking Cs were seared into the hindquarters of our brains. Chanel’s triumph was aided and abetted by Vogue, which in 1926 proclaimed the little black dress “a sort of uniform for all women of taste.” Thirty-five years later, Audrey Hepburn etched the little black dress further into mass consumer consciousness. Remember the opening scene in Breakfast at Tiffany’s, when Holly Golightly wanders the empty morning streets of New York City, lovely, lonely, vulnerable in a little black dress (designed not, as it turns out, by Chanel but by Givenchy)? Holly nibbles breakfast out of a brown bag and peers into the Tiffany store window on Madison Avenue. In fact, that very dress lives on, having turned up for auction at Christie’s a few years ago, where it fetched close to a million dollars—or four thousand times what we paid for Linda’s on-sale dress at Bloomingdale’s.

Okay, maybe the movies helped write the script. But hand the little-black-dress dossier over to an academically accredited Buy sleuth and you’ll get an entirely different explanation for what happened at Bloomingdale’s that day. Academics who practice qualitative research—i.e., those who, armed with clipboards, cameras, or binoculars, either in full view of subjects or concealed behind pillars, watch people shop and follow up what they observe with in-depth interviews—would seek to decode a pattern of behavior in my wife’s pursuit of the little black dress. I put the matter to Albert Muniz, who teaches marketing at DePaul University, specializing in how people form communities around the brands and products they buy. He told me he’d try to draw a finer picture of how the buying of the dress linked up with the occasion at hand—the fund-raiser—and what a woman such as my wife “desires to say about herself via the dress. To get at this,” Muniz said, “I’d interview that woman before she went shopping. I’d want to know plenty about her background, her life story, to gain a better understanding of where she was coming from. I’d ask her to take me on a tour of her closet, identifying favorite outfits. I’d want to know what her goals were for the event in question. Does she want to impress and influence others? And I’d like to accompany her as she went shopping, asking her to explain her choices. Finally, I’d have a follow-up interview after the fund-raising event. I’d want to know how it went, who was there, and how she felt about her purchase afterward.”

Muniz’s approach parallels that of Americus Reed, a young faculty member at the University of Pennsylvania’s Wharton School. Reed is a social psychologist by training. After I recounted the dress episode, he told me the impulse to purchase is related to our desire to obtain “feedback” in the form of social acceptance. Given that the evening was branded a “gala,” that it called for “cocktail attire,” and that Linda was inclined to dress appropriately, Reed said he would classify her a “high self-monitor”—one whose consumer choices enable her to “fit in,” to adhere to the social cues and behavior one attributes to a particular event or environment. To be a high self-monitor is to possess a chameleon quality: you buy and wear what you judge to be right for the occasion. Low self-monitors aren’t as much concerned with extracting positive social feedback. They buy and wear whatever they like to a school fund-raiser—mom jeans, if the spirit so moves.

Finally, a renegade anthropologist, Grant McCracken, who has taught at MIT and the Harvard Business School, offered me this elliptical response: “The Elizabethan Lord Burleigh removed his outer robes one festive occasion, saying, ‘Lie here counselor, while I go off to dance.’ An anthropologist runs the question in reverse and asks of a woman buying a new dress, say, what self do you take up with this dress, who will you now become?”

What McCracken was getting at: the little black dress, like so many things we buy, possesses a kind of transformative power.

Our journey had just begun, and one thing was already clear, at least to me: everyone has a take on what happened in that store, and no one knows for certain. When we look for all the possible explanations for why we buy what we buy, wear what we wear, drive what we drive, dine where we dine, or furnish how we furnish, we find ourselves adrift in explanations that range from the broadly trivialized—fashion victim! shopaholic! social climber!—to the truly arcane. There are those who would see Linda as a knot of sexual hang-ups, which we’ll come to. And there are white coats in neuro labs who aren’t the least bit curious about Linda the person but seek to understand her behavior in terms of switches and wires and electrical currents begging to be technologically scanned. There’s got to be a buy switch amidst all that static and ooze, wouldn’t you think?

© 2009 Lee Eisenberg