Man Repeller

Seeking Love. Finding Overalls.


By Leandra Medine

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Silk parachute pants. A gold lamé jumpsuit. Ankle boots with fringe. Were these fashion-forward items sending men running in the opposite direction? Maybe, but Leandra Medine never cared.

Slipping into drop-crotch shorts and a boxed sequin blazer in the dressing room of Topshop in downtown Manhattan, a brokenhearted Leandra had an epiphany. Looking in the mirror, she suddenly realized she didn’t have a boyfriend because of the way she dressed. And the more she thought about it, the more she realized that such outfits said a lot about her life-romantic and otherwise.

Now, in her first book, the acclaimed blogger and fashion darling recounts her most significant memories through the lens of her sartorial choices. With her signature sass, blunt honesty, and some personal photos, Leandra shares details of the night she lost her virginity right down to the pair of white tube socks she forgot to take off, as well as when and why she realized her grandma’s vintage Hermès ostrich skin clutch could hold much more than just keys and a cell phone. Through it all, she proves you don’t need to compromise even your most repellent qualities to find your way into that big white dress (and an organza moto jacket). See? You can have your yeti and wear it, too.

Showcasing the singular voice that has won Leandra millions of fans, this book is a collection of awkwardly funny experiences, a sweet love story, and above all, a reminder to celebrate and embrace a world made for women, by women.


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Copyright Page

In accordance with the U.S. Copyright Act of 1976, the scanning, uploading, and electronic sharing of any part of this book without the permission of the publisher is unlawful piracy and theft of the author's intellectual property. If you would like to use material from the book (other than for review purposes), prior written permission must be obtained by contacting the publisher at Thank you for your support of the author's rights.


Well, here you have it: My brain in tens of thousands of words, crafted to display an unfiltered glance into my thinly-veiled-by-chiffon thoughts. In order to protect the identities of characters crucial to the development of this book of essays, I have changed several names and, on the rare occasion, profession and geographic location as well.

You can rest assured, however, that each and every sartorial object depicted, dramatized, and described in the forthcoming pages is as authentic a nod to my memory as it is to the clothing that shapes it. Also, thanks for buying me. Let's get a drink when you're done.


I was lying through my teeth when I told Marla that a girl's first kiss is like watching fireworks, only even more magical. I'm still not sure what compelled me to say that to my cousin's thirteen-year-old daughter when I had been so resentful of my mother's wrongly romantic assertions about "knowing when you know" and "feeling right at the very pit of your existence." What is the pit of your existence? I should have told Marla what it's really like: slimy, awkward, and never ever as climactic as the movies that impregnate and then abandon your heart want you to believe. But maybe, too, my opinion was biased.

I didn't know much about the male species as a kindergartener, but I did know that I had a crush on a boy named Kevin. His hair was a silky bowl that almost always looked like it had been freshly cut. He didn't speak very much and often came to school with red boils on his arms, which prompted our teacher, Ms. Sherri, to send him home. I always felt a sense of emptiness when he left early—as though my existence at school was pointless and as though I'd wasted my good plaid dress or clean white turtleneck for nothing. On a Tuesday morning that I was certain he would be in school (our mothers had been on the phone the night before and I overheard mine say she'd see his at pick-up the next day) I walked into Ms. Sherri's classroom feeling particularly good about myself. Just after the previous night's phone conversation I had successfully lured my mother into letting me wear my favorite dress to school.

It was reserved exclusively for special occasions such as Rosh Hashanah dinner at my decidedly highbrow grandmother's house. But standing in my closet, I nudged at my mother's knee explaining why she should let me wear the dress to school. Even at six years old I understood the fundamental importance of calculating cost per wear. In a final fit signaling the brink of exhausted defeat (losing to a child is hard, I will give her that), my mom tried to threaten me. "If you dirty it," she warned, "I'm not cleaning it." It was difficult to take her scare tactics seriously. She diligently tried to instill the do-what-you-incorrectly-want-and-you're-on-your-own ethos in all four of her children, but when push came to shove we were never on our own. At the slice of a paper cut, there she was, with Neosporin, Band-Aids, and a phone at arm's length, should the emergency room need advance warning that we were coming.

"Oh my gosh! What a lovely dress!" Ms. Sherri offered when I got to school that Tuesday. It was lovely indeed; in a distinct hue of burgundy that predated the oxblood craze of 2012, my knee-length, tent-shaped dress featured a Peter Pan collar adorned with embroidered grape leaves, and housed an entire layer of tulle in its underbelly.

Age four: another such dress my mother also wouldn't let me wear to school.

"I know! Isn't it the best?" I gushed. Not very humble, no, but I was, after all, wearing the dress because I had won an argument about it—didn't that score me bragging rights? Hopefully, as Ms. Sherri did, Kevin would find it lovely and then subsequently find me lovely, too.

As I walked to my cubby to put my jacket and pink patent leather knapsack away and to fix my side-parted, side-clipped, shoulder-length hair, my two best friends Sarah and Rebecca walked over to me. I waited for them to compliment my fancy dress, but instead they just looked at me dumbfounded.

"You look like a baby," Sarah said. She was wearing a grey sweater tucked into a leather miniskirt, her hair in a half pony that looked like a chignon purchased in the sale aisle at Duane Reade. Rebecca, donning a similar hairstyle, concurred, and my ego fell to the ground. They were right. I did look a baby. I guess that's the thing about age-appropriate dressing—it's inappropriate. There was no way Kevin would care about my dress. How could I have been so silly?

A feeling foreign to me at the time, self-consciousness, reared its vicious head. For the rest of the day, I did everything I could to cover the dress. I took my jacket out of my cubby and put it back on. They made fun of me. I got hot, so I took it off and put it around my waist. They made fun of that, too. This was a no-win situation.

I looked at the clock around 11:50 a.m., fretfully dreading what would happen in ten minutes, when recess would start and I would have no choice but to face my friends again. Normally during recess, Rebecca, Sarah, and I would play house with Kevin. They had crushes on him too, but I was almost certain mine predated theirs and, as such, was much stronger. Kevin always played the dad, and the three of us, or rather the two of them, would fight almost every day over who got to play the mom. I wanted to be the mom, too; but I'm a lover, not a fighter, so I typically took the role of the child to avoid conflict. By then, I knew that on this day the girls would unquestionably liken my outfit to the role anyway. I already felt the lump in my throat signaling the imminent cry of defeat. I was trying to prepare myself when Sarah said it: "You have to play the baby because you're dressed up as one already."

I wasn't all that confrontational and thus allowed the following series of events to unfold as they would, with me sitting in a corner while they fought over who should be the mother and why.

"I'm the oldest," Sarah said.

"So? My mom said I'm going to be the best mom there is. I know how to cook vegetables," Rebecca retorted. The kitchen in our game was Fisher-Price, for heaven's sake.

I put my head down, though still paying distinct attention to their ridiculous squabble, when I saw a set of knees clad in khaki slacks bend and land directly adjacent to my own. I looked up and there he was: a rash-free Kevin. He moved from in front of me to directly next to me, and I felt his scaly hand clench mine.

The world stopped. I couldn't offer much attention to how coarse and unpleasant his grasp felt because my heart was beating so damn fast that I had to wonder if it might explode out of my chest. I was almost certain that I was seconds away from peeing in my pants. Sarah and Rebecca stopped arguing to acknowledge our budding romance, and as they looked over, unquestionable rage in their eyes, he kissed me on the cheek. Now I was certain I had peed in my pants, but I was too busy becoming a woman superior to both Sarah and Rebecca, in spite of my childish dress, to attend to that situation. We never ended up playing house that day, but it was clear that in matters of who got to play whom I was most definitely the mom.

"How did it feel?" Sarah asked amicably, as though she hadn't just hours before stabbed my pride in the heart.

"You're so lucky," Rebecca added.

"I know," I agreed. My aversion toward modesty struck again, if only for twenty minutes before both Sarah and Rebecca resumed their native positions as evil best friends and plagued me with cooties. For the rest of recess, my entire class, led by my two best friends, sang Leandra has cooties! Leandra has cooties! It was debilitating, really.

At afternoon snack time a few hours after Kevin had kissed me, Sarah asked him why he did it. (Who does that?) And Sarah had no problem sharing the details of a private conversation she'd held with Kevin and his friends. Apparently, his friends had dared him to kiss me when they saw me sitting in a corner, the tulle on the inside of my dress creating a thick, poufy puddle around me. "He wanted to give her cooties!" Kevin's idiotic friend Zachary had chimed in.

Sarah and Rebecca didn't talk to me for the rest of the day. And though my morale was now a bit lower and I was almost certain that the stress and abandonment had caused a rash to break out on my forearms, I didn't blame the yet-unfolding disaster on Kevin. Whether or not the kiss had been sincere, it was the most magical lip-to-cheek interaction I had ever encountered. And also the only, unless we're cataloging parental affection. I didn't blame it on my friends, either. No—if anyone was to blame, it was my dress.

When I got home that day, I ran to my bedroom, ripped the dress off my body, and proceeded to stomp all over it, wearing only my white wool tights and navy blue patent leather Mary Jane flats. Hysterical, I explained to my mother that I never wanted to dress like a baby again. That puddle of tulle that elicited the kiss offered up a generous serving of fresh squeezed humiliation. Why hadn't I just worn a white turtleneck and riding pants? My mom looked confused, and even hurt—it had been not even twenty-four hours since I'd begged her to let me wear that dress—but before we could resolve my despair, she noticed the unusual red blotches on my limbs.

"What's on your hands?" she interrupted my fit to ask, as the rash had quite visibly spread from my forearms to my hands.

"They're itchy," I told her, as she pulled my arms forward, examining the boils erupting on my skin.

She smelled them, though I'm still not sure why, and then affirmatively shrieked, "Oh my God! Leandra! You have chicken pox!"

She quickly removed what clothing I still had on and grabbed latex gloves from her intimates drawer, pulling them onto her hands. "Don't touch anything, especially your face," she cautioned. But why did she have my pediatrician's gloves in her underwear drawer? She drew me a bath, filled it with baking soda, and while supervising my bath time, asked me to tell her what I'd done that day "detail by detail."

By the time I was through, my mom assured me that Sarah and Rebecca were obviously just jealous and that I shouldn't fault my most favorite dress for their actions. At last my symphony began playing in harmony again. Of course they were jealous! Who wouldn't be jealous of a burgundy dress that lends no favors to the female figure and yet still incites a most romantic first kiss? I guess that's the thing about a first kiss: it doesn't really matter why you get it—what's important is that you have it.

And as for Kevin, "What an irresponsible mother he has," I later heard my mom tell my dad. "She sends her son to school in the final stages of the chicken pox and doesn't think to tell the teacher? Then my daughter has to catch it? I'm calling the principal."

Indeed, it seemed Kevin most certainly had given me cooties. I told my mom I hated him for it, that I couldn't believe he'd made such a fool of me, but the truth is I was pretty thankful. Chicken pox certainly meant I had to spend at least the rest of the week at home, which thereby meant a lot of daytime television. My first encounter with Jerry Springer manifested that week, in fact. Maybe in concurrence with my absence, my friends would feel bad for me and call to apologize, even.

As suspected, I stayed home the six subsequent school days. And also as expected, by the time I went back, though I was still thinking about the kiss, everyone had forgotten about my cooties. The case had been put to rest and I never looked back. But it wouldn't be for seven more years, as a freshman in high school, that I'd feel a boy's lips so close to my face once again.

By then, I'd learned that my mom had falsely advised me. My peers had not been jealous of my dress. For years I didn't know it, though, and every time I dressed like an asshole (my hair was very frizzy in middle school and I wore many a gold hoop earring) and someone called me out for it—male or female—I was certain they were either in love with me or simply wanted to be me. Neither scenario was accurate. Especially the one in which they were in love with me. No one was in love with me. In fact, I was getting rather antsy about it. All my friends had experienced their first kisses and I'd assumed that I'd probably been stricken by Judy Blume syndrome: after having waited so damn long to finally get my period, would I have to wait forever for my first kiss, too? I was the female equivalent of Peter Pan—only I really, really, wanted to grow up. Surely, this spoke volumes to my empathy for his eponymous collars, but ultimately had little to do with my baby doll tent dress.

One of my newer best friends (I'd long disposed of the malicious kindergarten duo), Rose, had her first kiss a year earlier while she was on a trip to London with her family. The boy was a friend of the family with whom she'd engaged in a minor flirtation for years. I thought he was imaginary, if only because I had conjured a pretend romance over the previous winter's vacation. (My "boyfriend" was called Kurt, and his skin was so tan, teeth so white, that he needed nothing but me to make him a better person.) Evidently, her dalliance was vastly different from mine in that her guy actually existed—she showed us pictures and everything. He clocked in at an impressive six foot four over her five foot six, and we wondered how thrilling it must have felt to fling her long arms across his high neck and embrace in that magical kiss.

Another close friend, Alison, had had her first kiss at camp during the Fourth of July fireworks with a boy who was three years older than we were. They'd been flirting for weeks, and the kiss was kind of inevitable. When we asked her about it, she just said it felt "right." Instantly it seemed that my friends who'd been kissed were notably wiser than I was.

Still another, Jessica, my third best friend, had had her first kiss at my house. With my brother. Once her parents found out about it they never let her sleep over again. We don't talk very much anymore.

I expressed concerns about my virginal lips to my mother shortly after the somewhat incestuous fiasco with Jessica. (A word to the wise: even if it is your best friend's first kiss and you are naturally inclined to beg for all the details—refrain if the other end of said first kiss is your brother.) My mother told me that when I met the perfect guy I would also meet the perfect kiss. But how would I know when he was perfect?

"You'll just know," my mom assured me, "at the very pit of your existence."

I imagined what "just knowing" might be like. "Hello, Leandra, I am the one," my suitor would say, standing six feet tall in a navy blue Brooks Brothers suit, wearing Alden loafers—the kind with tassels—and a patch inside his suit jacket that read Values: Leandra, Fun. "I just know you're right, at the very pit of my existence," I would rejoin, and we would kiss. My left leg would kick up, and fireworks would erupt. We would stop to look up at them and then look back at each other and smile, wholly aware that our minds were thinking precisely the same thing: Gosh, I'm lucky. We would spend the rest of our lives together, far too consumed by one another's ardent intellect even to bear the thought of another relationship, and just like that my mother would have been right.

Amid this daydream my mom also suggested that my braces might have been slowing down the process. This had never occurred to me, but it was then and there that I vowed to wear my rubber bands religiously. Two months later, the braces were removed. My mother was a wonderful catalyst.

I know, I know—I'm a babe. How could the inaugural kiss be taking so long?

One Saturday night, just three weeks after my braces came off, promised hope for the amendment of my social deficiency at a teen night in a grim, wooly New York City nightclub in Midtown called Cream. The event was sponsored by a charitable organization that tried to raise money for third-world orphanages, but really it was just an excuse for middle schoolers from all the city's private schools to get together. There would be no alcohol, of course. In spite of the burgundy tent dress disaster of my kindergarten days, I opted to wear a strangely similar short-sleeved brown tent dress that I had purchased from a boutique on 76th Street called Big Drop to wear for my upcoming birthday party—a monumental event, as it would take place for the first time without the supervision of my parents at a restaurant on Madison Avenue called Geisha. Naturally, I needed to look special. This one replaced that one as the best dress of all time, and I was so eager to wear it. It even had a Peter Pan collar, though this time without sketched grape leaves. It did not nest a layer of tulle, but that was a concession I was willing to make. The dress maintained the spirit of its notorious precursor, and I simply couldn't wait until my birthday (which was, by the way, nine months later) to wear it. It fell two inches above my knee. I would wear thick black tights under it and a black cashmere boat neck cardigan over it. "If Prada does it, we can do it," Rose's mother said about the blending of black and brown—though my own mother insisted the colors did not match. I would wear crystal-adorned black Marc by Marc Jacobs flats on my feet.

In hindsight, I might have looked like a Yeshiva schoolteacher on her way to meet a friend for Manischewitz, but in the moment, I felt like the coolest chick around since Tara Reid circa American Pie. My mom agreed and even forced me to pose for a picture in the hallway of our apartment building.

"You're really growing up," she said as she applied a minimal amount of blush to my cheeks.

"I am, aren't I?" I concurred.

But when I arrived at Cream and was greeted by my friends I realized I must have missed the memo on the dress code. Short black miniskirts with spaghetti strap tank tops and leather knee-high four-inch heel boots invaded the room. All of a sudden, my outfit fell flat. Especially the sparkly shoes—pun so intended.

Alison had snuck a water bottle full of vodka into the party. I had never tried alcohol before, and though I was curious, I stayed away. My parents had warned about underage drinking and the inevitability that I would choke on my vomit and die. I was gullible and in no way ready to face my own death. I hadn't even had my real first kiss yet.

Toward the middle of the night I found myself seated on a black leather couch all by myself while my three wing women found boys to kiss, because that's what you do after you've championed the first kiss battle: just keep on kissing more. They were all slightly tipsy, and I was massively bored. Angry, too, for again opting to wear a childish dress, this time on an occasion that demanded at least a subtle boob reveal.

A boy I'd never met walked over and sat down next to me. He seemed drunk, but I might have been wrong—at that time, my compass was still too raw and premature to pick up on such nuances accurately. He introduced himself as David and told me he liked my shoes. I immediately perked up and thanked him—how thoughtful that he had noticed! We were in a dark room, after all, and that sort of attention to detail takes training.

I couldn't yet rely on the solace of a cell phone to alleviate awkward social tension, so after I thanked him for the generous compliment and the conversation dissipated, I asked him what school he went to—there was no other choice. "Horace Mann," he responded, and some very uninteresting banter ensued for all of five minutes before his tongue was in my mouth.

The kiss was nothing that the very pit of my existence had insinuated. It felt like a slug was resting on my tongue and I was doing what I could to combat its slothful nature to no avail. No leg pop, no Brooks Brothers suit, no patch that listed values: my name and fun, in that order.

I heard Alison yell, "Oh my god! That's my friend over there—she's never kissed a boy!" but pretended I didn't and just continued kissing. Was this really what kissing was? The exchange of saliva and a motionless tongue? During the last seconds of our spit swap it finally hit me that I was having my first kiss. I thought to myself that maybe some men really did appreciate a woman who didn't bare it all, even if the woman in question was just a fifteen-year-old girl. David had, after all, complimented my shoes, which was probably only because I had been sitting down and he was unable to recognize the brilliance of my dress. Maybe what we were building was the very pit of my existence. And though it looked different from the picture my imagination had drawn, I have learned that there is a fundamental difference between that which the mind illustrates and that which reality portrays. I went with it.

By the time we stopped kissing, I had come up with all sorts of questions for David—I had every intention to learn more about him. Did he play sports? Was he a vegetarian? Would it be okay if I were one? Did he like going to the movies? I hated the movies and hoped he could get past that. Who was his favorite band? Would his mom fall in love with me as quickly as he did? He was obviously in love with me. But before I could get to any of these, David stood up and walked away. We didn't speak again that night—he hadn't even asked for my number. He must have just forgotten. Thanks to my highly advanced investigatory skills, I had learned via the minimal information we exchanged before our kiss that he was friendly with my friend, Erica. They went to the same school and, as fate would have it, were in the same class.

"Wait, you hooked up with David? David Feldman?" She asked upon my inquiry on the man who would forever hold the memory of my first kiss.

"Yes!" I told her, expecting that she would explain how dashingly handsome and sought after he was.

"He has a nickname," she told me. "Crusty the snowman."

That didn't sound particularly dashing. "Why?"

"Well, his ex-girlfriend told me that his jizz is crusty," she told me.

"And how would she know, Erica?" I asked defensively, as though she were revealing intimate information about my husband.

"Because she used to blow him and said it always tasted crunchy in her mouth."

My first kiss was with a boy who had semen issues at a club called Cream? It felt like Larry David was directing my life.

So ended the second shortest romance of my adolescence. My mother was now wrong about two things: Not everyone is jealous of me, and the first kiss is not perfect. At least I had finally gotten it over with, though, and now the floodgates of womanhood could open. But as my girlfriends continued to tally up their dalliances on a competitive scoreboard written into Jessica's locker (yes, really), my number remained stagnant at a depressing 1. I couldn't stop thinking about my short, albeit pathetic love history. I'd primordially fallen in love with a boy with a bowl cut who had given me cooties; and then, to finish his job, I'd allowed the immoral, thick, and slimy tongue of a teenager with a nickname that reflected the unhygienic nature of his semen to defile my virginal lips.

It was rather lucky that unlike Kevin, David did not go to my school and I could spare myself the humiliation of having to see his crusty ass roam the same hallways and locker banks that I roamed. Even in spite of that, though, it's tough to forget a first kiss. Much more, I suppose, when Facebook becomes involved. Last year I learned through the mutual friend function that David Feldman is now gay and happily in a relationship with Matthew Spielman. As for Kevin, the last I heard (read on his wall) he was still living in his parents' house, finishing up college a couple years late.


As a kid, I was neither particularly thin nor particularly heavy—that is, until the summer after eighth grade when I gained thirty pounds at camp. While most summer camps pride themselves on the innovative, competitive sports opportunities they provide, I didn't go to most summer camps. No, I went to Seneca Lake, located in the heart of Pennsylvania's Poconos. It was a camp inundated with the children of neurotic Jewish mothers; every child came equipped with at least one 20-by 40-inch plastic container full of artisanal goods such as Cracker Jacks, popcorn, Cheese Doodles, Milk Duds, Hershey's Kisses, and Twizzlers. Oh, the Twizzlers.

The campers of Seneca never had to worry about conserving these delicacies because when the supplies ran dry, mothers quickly and maniacally sent care packages full of replenishments. We'd heard horror stories from the neighboring camps about food-infested packages being confiscated, but the staff at Seneca understood we were growing, hungry, and perhaps most importantly, the products of anxious Jewish mothers whose priority was to feed us.

The first year my parents sent me to camp (my father made me write a list of ten reasons camp might feed my moral fiber when I begged to go), they didn't know about the Jewish American protocol that demanded they supply me ample junk food. Neither my mother nor my father was American, and the entire concept of summer camp was still as foreign to them as they were to the country.

"We're spending three thousand dollars to send her to sleep in a cabin for two months?" My dad asked my mother as he wrote a check to Camp Seneca Lake.

It wasn't just a cabin, though; it was the Princess Bunk. (No, really, that's what it was called.) We could get manicures on Sundays for heaven's sake! My friends, Seneca veterans, had very early on clued me in on the euphoric experience Seneca offered. I couldn't wait.

At the beginning of that first summer, I learned quite quickly that I was the only camper who did not arrive with a large box. I was also the only camper who had brought athletic clothes to camp. Sweatpants on a Saturday night and shorts and a white T-shirt (mine had silver dragonflies on it) on a Monday morning were colossal no-nos at Seneca Lake. This was a haven for denim and silk exclusively. Fellow campers didn't reprimand my lax style as much as they questioned it. It didn't bother me. But enlightened by the collective demeanor of all the Jewish American mothers' daughters, I returned home after that summer and imparted all my newfound wisdom to my own mother.

"I need to bring my nicest clothes and my own food," I reminded her daily for the three hundred days I waited until it was time to go back to the Poconos. Though she still wouldn't let me take all the clothes I wanted to—"If you ruin your favorite shoes and dresses, we will not replace them"—she did send me off with pretzels and Twizzlers and sour sticks and Gushers.

When I returned home after that second summer, thirty pounds heavier, my parents were mortified.

"Leandra! You look… you look… you look… happy!" My mother told me as I dragged my feet off the camp bus on 86th Street and Lexington Avenue, already depressed that summer had come and gone and that I had to wait another three hundred days to do it again.

"She's miserable," my dad said as he glared into my mother's eyes, still processing the sight of my stomach, which was now almost the same size as his.

I hugged my parents and started to cry—I was


On Sale
Sep 10, 2013
Page Count
256 pages

Leandra Medine

About the Author

Leandra Medine founded and writes The Man Repeller, a humorous website about serious fashion. It was listed as one of Time magazine’s 25 Best Blogs of 2012 and she was recognized as one of Forbes‘ 30 Under 30 in the field of Art and Style. She lives in downtown New York City with her husband and a topless stuffed doll that looks like Marc Jacobs. Visit her at

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