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  What’s worse than having no personal sense of style is having good taste in spite of it. I know what looks good on my body. No matter what fluctuations or unexpected thigh-meat situation occurs, I know how to flaunt the best parts while David Blaine–ing away all of the less wonderful parts. What I didn’t have was an aesthetic that I ascribed to, and thus my clothes never seemed to portray who I truly was. Game recognize game, but it’s no bueno when everyone else is a giant, novel game of chess in a rose-filled courtyard and I’m a knock-off version of Candy Crush on an iPhone 2 with the sentience to understand why an iPhone X is better.

  Admitting is the first step, but they should be more specific about who needs to admit to whom. I didn’t necessarily need friends and coworkers chiming in on my humble aesthetic in the big city, but that didn’t stop the director’s commentary on my ensembles.

  “Crocs are still Crocs, it doesn’t matter if that pair doesn’t say Crocs on them,” Angela, the woman training me at my first big city job, warned me. She was tall in a pair of black leather sandals (with straps), a simple black blazer and matching shell, skinny jeans (dark), and simple, small gold jewelry as an accent. In hindsight maybe she thought she was training me for more than an administration position in a dusty workshop.

  “But they’re comfortable, work appropriate, and I can walk from Grand Central to Coney Island and they won’t stink!” I protested, eager to have at least one article of clothing be deemed “not entirely heinous.”

  “They’re made of rubber. Are you a firefighter?” she asked without taking her eyes off the Excel sheet.

  “No.”

  “Is it raining?”

  “It wasn’t when I got off the train.”

  “Then they aren’t appropriate for anything besides ruining everyone’s day,” she punctuated.

  My shoes weren’t just ugly; they inspired mood-improving drug commercials.

  And it wasn’t just my unacceptable footwear that required attention. All my clothes felt dated. They were dated, even though I purchased most of them within the past six months.

  In New York, fashion has seasons, and style has a shelf life. Sex and the City taught me this, but it seemed too fantastical to be the reality of anyone who wasn’t part of a tight-knit group of friends who miraculously never had a work commitment during two p.m. brunches on Wednesdays. What else had I mistaken for parody on that show? Were people really skipping lunch to buy Vogue magazine? Could you wear a ballet skirt outside on any day other than October 31st when you’d aged beyond puberty and be called “chic”? How did I get this all so wrong?

  The “how” became immediately unimportant. What could be done to eradicate years of misunderstanding what was cheap but looked nice, and what was nice and looked cheap?

  After Angela had satisfactorily trained me in the arts of email response, cataloguing projects, and the best place to get lunch, I was on my own with my new boss, Betty. Betty was a petite, sixty-five-year-old woman with cropped blonde hair and a daily uniform of short-sleeved black mocknecks, a medium-thick black belt with a tasteful silver buckle, tailored khakis, and black loafers. Her only jewelry included tiny pearl earrings, a thin chain bracelet, and a watch. She subsisted on seltzer and popcorn from Grand Central. Timeless. Elegant. Controlled. Out of my price range. I had the “talk” with her about three weeks into working together.

  “Where did you get your loafers?” I asked, mentally double-checking that her classy, androgynous footwear were actually called “loafers.”

  “Oh these? I get the same pair every year from a shop on the Upper West Side.” She remembered, “They used to come in an alligator leather, but they discontinued that some time ago.”

  Some time ago. Even the way she spoke was fancy! It all felt curated, not in a try-hard way, but as if she were selecting each word like a regular ordering seasonal appetizers at a rooftop happy hour. I felt like I had spent my life to that point speaking a different language.

  “I don’t really know how to dress.” My confession hung in the air for a few moments, and then Betty patted my shoulder and told me to grab my purse—which was actually a Barnes & Noble tote bag.

  Betty had lived her entire life in Manhattan. She’d inherited her Upper East Side apartment from her mother and had rent control since the ’80s. Someone once told me that people from New York are like feral animals. They thrive only in cities and have their own knowledge and cool about the city that is definitively exclusive. People from New York don’t usually realize how expensive things are and how suburban the rest of the country can feel. Like when I read Lena Dunham’s book and she had a chapter that was her food diary and she was eating, like, celery foam and mushroom essence. I couldn’t relate. I didn’t know much about what Betty’s upbringing must have been besides rich (she mentioned ballet training and European vacations a few times), but I was happy to have a mentor who could get me up to speed sartorially.

  We exited the office and walked the half block to Madison Avenue to board an MTA bus. I had never taken a bus in New York. Locating my MetroCard was a daily struggle, but luckily the additional turnstiles in the subway gave disgruntled passengers an escape from my ineptitude. The bus riders unfortunate enough to be stuck behind me became a captive audience for my panicky attempts to shove the card in the machine the right direction and keep it moving.

  Betty, ever city-cool, put her card into the bus’s machine slot twice, getting us both on with no hassle. As we rode uptown she told me about all of the iconic stores. Their names all sounded to me like variations of that elderly Muppet duo that routinely heckled Kermit in the theater. This store had closed. That store moved downtown. This one was probably going out of business in a few years because Manhattan had really lost its influence to Brooklyn.

  Arriving on Fifty-Somethingth street, we walked over to Bergdorf’s (the Muppets’ cousin’s house, presumably) and sauntered inside. Did Betty realize that she was paying me five hundred dollars a week before taxes? That when I had “spending money” I meant I’d saved an extra twenty dollars one week that could go toward a grandma slice of pizza and maybe a mani sans pedi at the questionable place in my neighborhood on a Saturday?

  Immediately upon entry I watched two salespeople spot us, and then look at our feet. One salesperson approached Betty and was off to the races describing the layout of the store as if it were the key to finding buried treasure. I was apparently beyond help and remained ignored in my depressing footwear.

  Unsurprisingly, as we moseyed through section after section of fine silks and suede from every animal, I, without exception, chose the most expensive items as my favorite on each rack. As we walked, Betty talked about her theory of timelessness being the only goal in fashion and that the rest is just there to trip us up.

  “This is the kind of store you should be shopping in. You don’t have to buy much, because all of this is classic. So think of it as acquiring, not shopping,” she said, as I tried desperately not to roll my eyes. It’s a very romantic approach to dressing, but I’m broke, dude. Get real.

  * * *

  * * *

  Weeks later, by complete accident, I attended the final “Fashion’s Night Out,” an event started by the fashion industry after the economy tanked due to the 9/11 terror attacks. This pregame for fall fashion week was an effort to get locals out and shopping at every store, enticed by the promise of sales, photo ops, and free snacks. My office was amid the hubbub, so walking to schmancy stores wasn’t adding many steps to my day. From a distance I watched Kim Kardashian sign bottles of some fragrance she was hawking (I was absolutely not about to pay sixty dollars to smell like a magazine subscription just to get face time with Kim K.), and I saw Kristi Yamaguchi conversing with the winner of some fashion reality show. I hopped from store to store down Fifth Avenue on a humid September evening watching bloggers and hopefuls pose, desperate to be featured in street-style roundups the next morning. I reali
zed my fashion dreams were not so deep.

  My style has evolved every year of my life, and there are still days when you will catch me wearing gym clothes with no intention of setting foot inside nary a locker nor weight room. Still, I think I figured it out. Here are the only fashion rules that I try to care about:

  1. Wear things that flatter your skin tone. For me and my melanin, that means the richest royal blues, ruby reds, pastels, mustards, and of course . . .

  2. Black. Black is always right. Black always looks good. Do that.

  3. Clothes should work in tandem with natural assets. Ruffles are dead to me. My ’fro shouldn’t have to compete with ’70s Elton ruffles.

  4. Shoes have to be comfortable. They also have to be cute or true neutral. I have no problem having unremarkable shoes. My problem is low ankles that get cut by cute shoes and hobbling up and down the stairs of subway stations, desperately hoping that there’s enough space for me to sit for my sad sack ride back to Brooklyn. TL;DR: if no one remembers your shoes, that’s still a win.

  5. Try to avoid buying anything I’ve seen my friends wear. I am always inspired by the people I know, but the original is always better than a copy.

  I’ve since fallen out of touch with Betty, though if I’m being honest, I didn’t have much in common with that rich old white lady to begin with. If I had to imagine, I’d suspect she’s still rocking a very Warholian style of clothing, sustaining life solely on LaCroix and air-popped popcorn and yelling at some poor girl to draft an email for her. Whoever that girl is should absolutely ask her how to upgrade her wardrobe, and then probably start applying to more lucrative jobs. That’s what I did, anyway.

  Starstruck

  My favorite question to get since I moved to New York is “Oh my god, how many celebrities have you seen?” The answer to this question is a Mean Girls–ian “The limit does not exist.” What I love about this city is that everyone seems to be vibrating on his or her own wavelength of celebrity, and because of it you start to forget to care.

  But to my discredit, I have a nasty predilection for embarrassment, and there are a handful of celebrities before whom I’ve humiliated myself. Here’s a list:

  Max Joseph (the silver fox from MTV’s Catfish): On the set of a commercial and called him a “droll” when my brain attempted to say “dream” and “doll” at the same time.

  Darby Stanchfield (the redhead from Scandal): Saw her on my Delta flight and tried to sip from the stirrer in my drink. Pretty sure she saw.

  Cassie Ventura (singer of the mid-2000s hit “Me & U” and P. Diddy’s girlfriend? I think?): We were seated next to each other on a flight to LA, and I knew too much about her time modeling for the Delia’s catalogue and brought it up. Then I told her that “Me & U” was my first purchased ringtone and proceeded to overexplain that it was chosen because the opening lines are “You’ve been waiting so long, I’m here to ANSWER YOUR CALL,” get it?

  Jessica Alba: I was at a party with another YouTuber, Rosianna Halse Rojas, and requested a selfie, and when she refused to acknowledge our presence, her husband offered to take the photo for us.

  Jenny Slate: Was interviewing the cast of a movie on the red carpet and asked if she thought Hollywood was a “boys’ club” and she got really mad for some reason and told me that “all of her success was thanks to her personality and all of her failures were, too” and I frowned at her lack of engagement with the inquiry.

  Matt McGorry: While attending a charity dinner I ran into him, and as he was looking for a seat I made him sit next to me in what we later determined was a toddler chair. I forgot to get silverware and ate broccoli with my fingers in front of him. There was probably/definitely broccoli in my teeth, too.

  A model I follow on Instagram: I couldn’t remember her name, so then she thought I didn’t know who she was but I totally did and it was so bad.

  Hayley Hasselhoff: We met at an event where we were both speaking, and even after she told me her last name I asked her where she was from and never put it together that her father was Knight Rider.

  Javier Muñoz (actor in Broadway’s Hamilton, In the Heights): We were at a potluck, and while someone was making an important speech, my fork started falling off my plate and he had to catch it so as not to have it make a more cacophonous noise. The prong side of the fork, too. That I’d had all up in my mouth. He was way nicer about it than I would have been.

  Marc Lamont Hill: A friend asked me to do a reading of her pilot at her apartment building and he walked in, which would have been fine except I thought he was my friend Desmond from improv.

  Donald Glover: I met him on the street while he was carrying a ton of groceries and had his headphones in. I made him take off his headphones and told him how much I adore everything he’s ever done (yes, I used those words) and then begged for a selfie. He declined and I was like, “Okay.” But I still posted about it online. Later, my friend Baze told me she was hanging out with Donald (first name only) and I spazzed and begged for an invite, and then when I arrived at the hotel party, I hugged Baze and knocked her wine glass out of her hand and then Donald and I had to work together to clean up the wine and broken glass. (Also, he apologized for turning down the selfie because he was in a bad mood earlier because a cab wouldn’t pick him up and he had to walk two miles with groceries back to his hotel).

  Christina Caradona (fashion blogger): Saw her while I was drunk at a Tumblr party and proceeded to tell her that I thought if my ex-boyfriend and I had babies they’d look like her.

  Padma Lakshmi: I’d been invited to an event for her book and I promptly started complaining about how hard it is to write a book, but luckily she’s super chill (considering how gorgeous she is) and she was like, “Omg, it was the hardest thing I’ve ever done. Books!” and I felt better.

  Michael B. Jordan: I’m not sure if I verbally asked him to marry me or if it was in my head and now I’ll never know. If you’re reading this, Michael, I think it’s cool your parents live with you and I think we would make a great pair.

  New York

  WHAT’S GREAT ABOUT IT?

  Diversity, opportunity, and style.

  WHAT SUCKS ABOUT IT?

  It’s the most expensive cesspool in which one can live.

  End of My Relationship

  The Brooklyn Museum is fancy. You might not know that if your frame of reference for New York museums are MoMA and the Met. But situated adjacent to the botanical gardens, the Brooklyn Museum in Prospect Heights is an imposing structure with a grand ivory staircase, fountains, and an all-glass, high-rated restaurant in front. This very restaurant was the site of a dinner that changed the course of my life forever.

  Jazmine Hughes is not my little sister, even though I still tell people online that she is. In addition to being black and having the same surname, she’s a wunderkind; an editor for the New York Times Magazine, she has bylines all over town and is also beautiful and younger than me. Am I jealous? Who isn’t? But this particular night she was profiling the Michelin-starred restaurant Saul for New York Mag, and I was her guest. Up until that night, in my New York tenure the fanciest thing I’d eaten was brunch in Williamsburg, which is basically just overpriced eggs, toast with nuts, oats, and more debris in it, and a side salad covered in oil and balsamic instead of ranch. This was going to be an experience.

  I cannot recommend highly enough befriending someone with access to Michelin-starred restaurants that *checks Yelp* no longer exist but had high ratings from tourists and locals in their lifetime. The chef will do everything to impress you even when you come in wearing your Target best (which is all I can assume I was wearing because what other clothes did I have?).

  “I’m meeting Darn’s family over Thanksgiving,” I nervously began. “I’m going to be in Nebraska with a white family I don’t know for five days. No, he’s never had a black girlfriend before.”

  Jazmine took a long sip of
her first free cocktail that night. She wasn’t stalling so much as preparing.

  “Well, I’ve been with Steve for five years, so we’ve crossed that bridge, but here’s what you should expect.”

  “Oh god,” I said with a mixture of equal parts nervousness and intrigue. I took out my phone.

  “This is off the record!”

  “I’m not scooping you, I’m just taking notes! Damn, how bad is it?”

  “Okay, we’re back on.”

  As the first course of many was brought to the table, she began.

  “The good news is the novelty will wear off after about an hour. But that first hour is crucial. They’ll ask you a bunch of questions and try desperately to relate. Throw them a bone here.”

  “How?”

  “Tell them you like Elton John or the Beatles. That’ll give them the assurance that there’s any common ground.”

  “Really?”

  “Ha, no.”

  Two more presumably free rounds of drinks, please. We’re going to be here awhile.

  The truth is the only other time I’d met a boyfriend’s parents, they were visiting Disney World (where their son and I worked) and were far less concerned with liking me than with talking to every cast member in Epcot about what their home countries were actually like. We hadn’t been dating as long as they had been planning their vacation and wouldn’t put this encounter on much of a pedestal. This, conversely, would be five days of unrelenting hangout in Omaha (white), Nebraska (whiter), with a family that was invested in familial tradition. Had I taken Darn to meet my mother in Kentucky, she likely would have picked us up at the airport, taken us to dinner, and then expected us to spend most of our time at the mall or a variety of chain restaurants’ happy hours without her. Darn’s family went camping together every summer. My family went on all of one vacation together when I was in high school. We didn’t play Munchkin with all of the expansion decks. We played Spades once a decade and inevitably I’d renege and be banned from ruining my uncle’s chances again.