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Obsessed with the Dresses

by Lisa Levy

I can date the obsession back to its first day, using my buyer history from Etsy and eBay: April 1, 2013. On that day I bought two 1960s dresses on Etsy: a super mod gray cotton blend dress with buttons on the collar and the skirt which the seller, Where Are They Now?, called The Majorette Dress, and a white long-sleeved polyester number called The Space Cadet dress (I will refer to the dresses by their names throughout, as the sellers on these sites treat the clothes with a kind of reverence that I admired). Unlike some stores I went to again and again, I don’t think Where Are They Now?  became one of my usual haunts. I know because I have these electronic trails of all of the dresses I loved, I bought, I lost.


 I still love the Majorette dress while the Space Cadet dress was kind of a disaster, totally transparent and hugging my bulges in all the wrong places (this is a lesson I forgot and had to relearn about polyester throughout my dress buying binge, as it is the most unforgiving of fabrics). I struck again on April 3rd, buying three dresses from a store called Neon Threads Designs in Oregon. I bought a Red Mod A-Line Mini Vintage 1960s Retro White Piping Details Bright (which was marked M/L and was way too small, I quickly learned I was not a medium in this world), a Black 60s Dress Vintage mod Shift Little Black Dress Sporty Front Zipper White Pattern Mini (a large, which fit), and a striped Navy Blue White A-line Skirt Colorblocked 1960s 1970s Indie Retro dress, which also fit fine. My total at Neon Threads was $111, so it was around $37 per dress including shipping: my target for dresses was between $30 and $40 dollars, so this was a good haul. Meanwhile, on April 9, I bought two dresses on eBay, a 1960s poly textured Jackie O Mod Shift Dress and a 1960s mod Gogo Twiggy Stewardess poly dress, both from a buyer named dani_pulsar based in southern California, where I knew the thrift shopping was a goldmine once you left the hipster confines of L.A. I bargained my way into a $10 discount in buying both dresses, so my total was only $74.99. 


My obsession with vintage dresses has been with me my whole adult life: when I was 16 I bought an amazing raw silk hot pink 1960s dress and jacket set at a thrift store near my summer camp in Connecticut, which I still have. I remember the purchase well, since it was at one of the few stores in Sharon, Connecticut, a charity shop in the same strip mall as the laundromat all the camp staff used on our days off. The collar of the dress has silver tinsel and pink and white jewels sewn on it; it’s very Jackie Kennedy with a dash of That Girl. 


When I was in my 30s, in a previous hardcore vintage phase, I spent a lot of time and money at a store on 19th Street in Manhattan called Darrow. Darrow was also the name of the owner, a flamboyant woman with long blond hair and short bangs, who I never saw in anything but perfectly accessorized dresses from the 1940s with a slash of red lipstick on her perpetually moving mouth. Darrow taught me a lot about vintage shopping in retrospect: how to make a dress right for you with alterations, and that my best era was the 1950s and early 1960s, as I am a classic hourglass with a considerable bosom. The store wasn’t cheap, but her merchandise was excellent, though I’d also peruse the racks at other vintage stores around the city, like Andy’s Cheepies and the Antique Boutique on lower Broadway and Starstruck in the West Village (RIP, alas, to all these stores, especially Darrow). I took several of my girlfriends to Darrow, and everyone became a customer at some point, since Darrow was the most charismatic and persuasive salesperson I’ve ever encountered. She also loved to give advice on other life matters, especially men: she told me she never let her husband see her in anything but 1930s and 1940s lingerie, no flannel or cotton pajamas would do. When I was going through a weird and rough breakup, she suggested I meet the guy for breakfast or coffee and casually drop a pair of underwear as I got my wallet out to pay, as if to signal I’d spent the night elsewhere. I followed her sartorial advice religiously but never did that underwear trick. 


When I started buying vintage online, I knew it was mainly because of the weight gain but I also loved being absorbed into past worlds again. Online the merchandise was so much vaster than it had been at brick-and-mortar stores; it was thrilling to have so much to choose from. Those Post-Its on my desk represented possible new wardrobe worlds to me. As I took that deep dive into Etsy and eBay, discovering 1950s and 1960s (and even 1970s) designers I liked, I was educating myself on this new world of vintage dresses. The obsession followed quite naturally, until I didn’t want to wear anything else: all of my clothes, the ones that still fit, seemed pedestrian by comparison.


I also learned to shop by measurements, which was much less stressful than shopping by conventional sizes. Yes, I would pay for ignoring this weight gain, and yes, I would pay for the obsessive spree which resulted from my dress passion as I went from shopping while I was terminally bored at my high-paying corporate job to having a superabundance of dresses (way more than my closet could hold), an embarrassing amount of debt, and no job. But I also reveled in my obsession, and still do: the dresses make me feel powerfully feminine, and I love the idea of wearing things you would never see on anyone else. Personal style has always been paramount to me, and wearing vintage is a hallmark that you are beyond trends, too good for the blandness of Banana Republic or the garments at H&M. 


I love spending money; buying things I want, objects of desire, not the stuff of necessity, soothes me. But I also love having money: seeing a healthy balance when I check my bank account makes me feel safe and secure. So the paradox is every time I spend money on something frivolous I feel a frisson and then guilt sets in, and as these things are usually purchased online the process repeats when what I’ve ordered comes (hooray, I love it!) and then the deflation as reality sinks in (oh God, my credit card bill). 


The shame I felt around my weight gain and the lengths I went to hide it even from myself is an issue that particularly affects women: we are our bodies, our appearance is paramount in our self-worth. I can’t remember a time in my life in adolescence or beyond when I wasn’t weight conscious, and my current situation was particularly odious because I had already gone from overweight to thin once before. It felt I was enacting Elizabeth Hardwick’s description of Simone de Beauvoir’s The Second Sex: “Like woman’s life, The Second Sex is extremely repetitious and some things are repeated more often than others, although every idea is repeated more than once. One is justified, then, in assuming what is repeated most often is most profoundly felt.” For me, gaining and losing weight was one of my most profound felt narratives. I knew in my soul the difference in the way the world treated you when you were 125 pounds compared to, say, 175, or worse.  So now that I was heavy again I was scrambling to make my appearance interesting through the dress obsession, as if that would compensate for the extra weight. To be interesting is not to be thin, but maybe it would do. 

The unnamed backdrop to all of this is how I got from 125 (really, it was more like 135) to the unnamed worse number. Yes, I am one of those people who has a tendency to gain weight, which is why I have to exercise or face the numbers going up on the scale. I write that as if it were a straightforward sentence, when it’s actually knotty as hell: when I think about it what careens through my head is everything from an angry, “Why me?” to a woeful, “That’s just how I’m built.” This is a sequence of thoughts that’s familiar, as it’s the same with my chronic migraines, my recurring depression, and my acute anxiety, but those conditions I medicate and otherwise have very little control over. Food I’m supposed to master, and yet I let it get out of control because I did something everyone wants to do, even longs to do: I fell in love, and love made me fat. I was as gluttonous in love as I was at the table; as I’d never fallen in love like this before, I’d never let myself go like this, emotionally or physically. Love distracted me from staying thin, so I ended up with a healthy appetite, a wardrobe that no longer fit, and a new online vintage dress obsession to fill my long days at the office.   


There is a reason why shopping is usually relegated to a montage in the movies: unless you are the one doing it, it’s not inherently interesting. But I think of shopping, especially online, as a video game for women: nearly every female friend I have plays at putting garments or goods into a cart on a website and abandoning it, as if just going through the process of picking out what you would buy is enough to satisfy the need for the new.  Lots of people simply buy what they need, though here in capitalist America many more people buy plenty of things they don’t need, which is the category I fall into. It’s what I don’t need and I’m still buying that changes. Sometimes it’s books, which is ridiculous since I’m a book critic and get free books by the truckload. At times it’s been music, though in the age of Spotify buying music is an obsolete notion. But clothes—I was rigorously trained by my mother in as a child brick-and-mortar discount shopping, with its communal dressing rooms and other minor humiliations. It’s exhausting to think about now, sorting through endless racks of disorganized merchandise to find sizes and styles and then dragging piles of things to fitting rooms, occasionally padding back onto the sales floor in my socks to find another size or style (discount stores aren’t big on sales people to help you). 


Part of the insidious nature of online shopping at work was that I could spend money faster than I was making it.  I loved trolling for bargains. Thus began the system of Post-It notes full of options and alternatives. Once I found two or three dresses I liked at a store I started my calculations so I could bargain the store owner down, usually trying to get around a 10 or 15 percent discount. This was a platonic form of shopping. It was just me and the computer, with endless computations and combinations. I loved the hustle of it, the fantasy, filling my closet and eventually some overflow spaces with illusions of people I might never be, with dresses I might never wear.  This is where the wonkiness of measurements comes in: sometimes it was my mistake, sometimes theirs, doesn’t matter. That illusion does. I have outrageously bright sundresses à la Laugh In and polyester sets that make me look like I’m campaigning for Nixon or guest starring on The Avengers as Emma Peel’s fat, funny friend. I have plaids and paisleys and florals—so many florals—and itchy boiled wool sheaths and soft cotton pseudo kimono 1970s shirt dresses. I have thick, thick polyester and whisper thin cotton that’s obscene without a slip, though I hate slips. I can barely count the dresses, they boggle the mind and dazzle the imagination. And when I think about them I feel a little bit ashamed, more than a little bit excited, and I wish I had more. 


At first, I just ordered things I liked and I thought might fit me, but after a couple of serious misfires I started keeping my measurements handy. I don’t know why the measurements did not bother me the way sizes did. They played into my body dysmorphia although they were as cold and hard as facts could get. They too were much bigger than I wanted to be, but I think I wasn’t used to thinking about my body in that way). But dresses are usually measured at the bust, at the true waist (the narrowest part of the hourglass), and at the hips. With the swing dresses I was shopping for I ran into the most problems at the hips, as mine are peasant style, low to the ground, made to tend the hearth or work the field. Willowy is not my adjective. Neither is lithe. I could get around this by buying dresses large and then having the top taken in by a good tailor, but that meant another step and a jump in price. Plus, I started to fall in love with particular designers and manufacturers, which complicated things, as love tends to do.


Here’s another early haul: on April 11, 2013 I bought three dresses for $110.45 from Concetta’s Closet in Portsmouth, New Hampshire, which is a brick-and-mortar vintage store that also operates on Etsy. This is when I was still feeling out my size, because looking at the order I can’t remember ever fitting into the vintage Lucky Kelly Green shift dress I bought. I do remember wearing the black polyester mod dress with a nautical neckline and two rows of buttons running down the front, and I might have been able to squeeze into the Fruit Punch Pink 1960s dress that rounded out the order. Given how low the total price was she must have been having a sale: she had good stock and she knew it. She used this adorable gamin model complete with Rosemary’s Baby Mia Farrow hair for all of her merchandise photos, so the clothes looked fantastic, though that woman was probably a size 2; it’s common to pin larger garments to smaller bodies in photographs when you sell online. 


By late April my obsession was in full swing. On the 25th I bargained with a store called Great Lakes Outfitters in Minnesota which had shops on eBay and Etsy and got four dresses for $128 (Kelly, the proprietor, marked everything down to $32 a dress, just about meeting my offer of $125 for four dresses). From her on eBay I got a black bombshell 1950s party dress and a red and white scooter dress. On Etsy I got a bright green swing dress with a white stripe down the front and around the collar and a Peck and Peck orange sherbet shift dress with giant buttons (I love giant buttons, and fabric covered buttons, and I’m a sucker for rick-rack too). The cotton dress was shockingly heavy, lead apron at the dentist heavy, like something for winter adapted badly for summer wear since it was short sleeved. It was marked large but my more than ample bosom strained the adorable buttons from the jump. They wouldn’t lie flat, and combined with the barbaric weight of the dress, I felt self-conscious and didn’t wear it much. I loved the bright green and white dress, which had a cool texture of pleasing squares. It was too long so I had it hemmed a smidge too short, a mistake I made often enough to be self-aware about but not so often that I told my shrink about it. 


On April 28, I bought a Lily Pulitzer (a popular resort wear designer, think Palm Beach preppy on acid) with a red and pink print and white rickrack down the sides at a decent price, along with a green and blue mod dress with a scarf collar (I grew to love these in their dated, dashing, Mary Tyler Moore-ness), from a Minneapolis vendor called Ms. Tips for $144. The next day was my second purchase from Tush Vintage on Etsy, run by Elizabeth from Pennsylvania, who became a pal, emailing with me about our passion for bracelet sleeves (3/4 length to show off the aforementioned jewelry) and winter coats with fur collars. This was a relatively expensive purchase, two dresses for $105: a L’aiglon dress with matching scarf and belt that fit me briefly and was in this to die for wild chiffon print, and a conservative linen polka dot dress which would have looked cool and lean on someone taller and less Jewish (again, my peasant body turned prep to frump). My first purchase from Tush had come about a week earlier, on April 19, when I bought an awesome scooter Jonathan Logan white day dress with a high-waisted belt which turned out to be a disaster on because it was translucent polyester and the belt turned my boobs into a giant shelf. I also bought a John Abbott Op Art shift dress (Abbott is one of my favorite designers, very psychedelic, often using graphic elements and flowers in the same fabric); and a summery shift dress by the appropriately named Shifts Internationale of Miami for $169. No wonder Elizabeth was so quick to befriend me.


I didn’t shop everyday—well, I didn’t buy everyday is more accurate. Nearly every day I had a list going or I was watching an auction or keeping a tally of what was appealing to me at some store. Sometimes I’d wait for there to be more than one dress I wanted so I could strike a bargain. Later, when I honed in on the labels I wanted, I bought more quickly, but in the beginning it was fun and giddy and I wanted the clothes as much as the amusement. I wanted something to take me away from the quotidian, especially my job. My May/June weddings were just about planned. My migraines were unrelenting. I wasn’t writing. I was in a weird liminal state, and these dresses were filling my time and my imagination. I was shopping for a more interesting life, and I tried to see a less stressful and happier time in the crystal ball of Etsy and eBay. 


I was closing in on what should have been the happiest time in my life: my wedding, which for complex reasons was actually a series of events. But I was also miserable: working a job I hated, not writing (my choice, I decided to take a break from freelancing while I was wedding planning), stressed about the weddings all going according to plan (we had a city hall ceremony and two parties, one for our friends in Brooklyn and one for our families in Florida, so there was a lot of planning to do), getting constant migraines, and feeling helpless to stop the pounds piling on me. So I kept thinking about dresses, and looking at dresses, and shopping for dresses, and buying dresses. In retrospect, it was an astoundingly stupid way to self-soothe. I needed the money: we were paying for the wedding parties ourselves, my fiancé had just started a business that wasn’t profitable yet, and I had plenty of clothes. A good portion of what I bought didn’t even fit or had to be altered. I didn’t need a constant reminder that I was gaining weight, and yet nearly every package held one, a dress where my measurements and the seller’s didn’t quite align. 


And then came Vested Gentress.


Vested Gentress was a mock preppy designer from the late 1960s into the 1980s that made summer dresses, as well as some skirts, skorts (for golf) and t-shirts, but you mostly see the dresses around. From the Vintage Fashion Guild, one of the few online sources for information about these labels, I learned: "Vested Gentress was established in 1961 and was based in Valley Forge, Pennsylvania. Their factory was located in Trappe, Pennsylvania, about twelve miles from Valley Forge. The company was known for whimsical screenprinted fabrics. These fabrics were made into dresses, slacks, and skirts. They also had a line of golf wear. The company closed in the late 1980s." Such a bland description for a manufacturer of amazing clothes. I found myself buying a few as the prints are amazing—a blue dress adorned with doves wittily carrying bells in their beaks; a long white dress with rows of bright green frogs accented with yellow connected by their jauntily crooked arms; white outlines of horses against a blue gingham background with the horses’ behinds depicted on the back, and probably the prize of my lot, a maxi dress featuring alternating turquoise and green pirates and associated parrots—and then I began collecting obsessively. Unlike most of what I bought, which isn’t particularly collectable, these dresses have other hardcore followers. I don’t really believe in buying anything vintage and not wearing it, though I eventually forced myself out of most of my collection with my steady calorie consumption. But looking over my records for the summer of 2013 I bought around 20 Vested Gentress dresses in various shapes and sizes, averaging at around $30 (the pirate dress was a three-digit splurge since it was rare and was in perfect condition). 


Yet the point is not the money I was spending, but the rate at which I was buying them: from May to early September 2013 I bought at least one dress a week, and up to three dresses during heavy weeks. And I was buying other dresses besides Vested Gentress too. The obsession was in control of me. I thought Vested Gentress was special, a ticket out of my misery; that it was impossible to feel sad while wearing a cotton candy pink dress with giant green grasshoppers and a green rope belt. It was the only way I could make myself feel better, even momentarily, because in the big picture, despite my upcoming wedding and the honeymoon in France a few months later, I still felt lousy. I hated my job. My migraines had increased frequency from three to five a week to everyday, and even getting infusions of a migraine fighting cocktail (an anti-nausea drug, an anti-inflammatory, and some Benadryl) at my neurologist’s office wasn’t helping. I had an infusion the morning of my bachelorette party—which was not a drunken free-for-all but fancy pedicures and a lovely dinner with some close friends—hoping the infusion would knock the headache down to the point where I could enjoy a couple of drinks. I had the drinks, but with the migraine on the side, and as a chaser later too.


Where did I expect to wear these dresses? Was I shopping for someone with a different life? There was no dress code at my job, and I wore a lot of what I bought to work, though some of the hardcore polyester was itchy and unflattering and felt like a costume (especially the dress sets, which made me feel like a bit player from a scene on Mary Hartman, Mary Hartman). Usually once I paired a vintage dress with my scuffed up shoes or sandals it just looked like clothes, and since I lived in Hipsterville, USA in Brooklyn and commuted to midtown Manhattan I often didn’t get a second look. The train was too crowded to gape; plus, I was vaguely middle-aged and decidedly not hot by New York City’s emaciated standards. My coworkers got used to my odd acquisitions, and the few who complimented me got an earful about whatever I was wearing that day, though no one but my officemate knew how much work time I was spending shopping. As we all worked for the same insane, exacting family doing their bidding most of what we did was complain about our jobs, not talk about our lives. 


There is a distinction between obsession and addiction. The language of addiction feels natural when I’m describing shopping for the dresses since I felt so out of control (but, I should add, not unpleasantly so, except when the bills came due), and I could argue that since I was shopping for dresses every day and it definitely gave me a rush that I was addicted. But that period did not last long, and I did not physically need help in order to stop shopping. Now I associate the vintage dress obsession more with gluttony, or self-indulgence to the point of self-disgust. The parallel to my weight gain is obvious, alas, since my shopping indulgence went hand-in-hand with excesses at the table. The irony was I was eating myself out of the clothes I loved.

The shopping for dresses didn’t end until I left my job in July 2014. I had not had a single flare up—except for buying a couple of necessary coats—until I wrote the first draft of this essay, and all of the feelings I had about shopping and buying vintage dresses came tumbling back. I bought three Vested Gentress dresses on Etsy and one on eBay in the course of one morning. I did it exactly as I used to, and it was like falling off a bicycle: I searched, I made notes, I did calculations to figure out what a fair offer was for the three dresses which were all in the same shop, offering around 15 percent under the full asking price. My offer was accepted and I engaged in some email chit chat with the owner of the shop, who had bought all of the Vested Gentress dresses at the same estate sale which made sense as they were all roughly the same size. The eBay transaction was clean, I just bought it and it came: it’s an unusually sedate Vested Gentress dress which almost looks like it’s by the designer Vera, she of the ubiquitous 1970s scarf, with a bright yellow background with a large blue and green flower. The Etsy Vested Gentress dresses were a 1970s Purple Turtle Tortoise Flowers Grass Novelty Print; a Vintage 1970s Floral Novelty Print Dress; and a 1970s Pumpkins Squash Gourds Dress. I cleared some stuff out of my closet from the last couple of years to make room for them. I hung them carefully, with their contrasting rope belts thoughtfully draped over the top, ready to wear. I love them.

About the Author

Lisa has been a freelance writer for almost 20 years. She has written for many publications, including The New Republic, the LARB, the Believer, the Millions, the Rumpus, TLS, and Lit Hub, where she is a contributing editor. She is also a columnist and contributing editor to Crime Reads. She has work forthcoming in Boulevard, the Harvard Review, Brevity, the Missouri Review, and Jezebel. Her website is

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