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“Anna Wintour lives next door you know,” Kelsey, the big haired, big breasted, stout cashier informed me.
“Shut. Up. You’re lying!” I replied astounded. The Anna Wintour, of Vogue Magazine, the first and last word in fashion.
“Yeah, I’ve seen her a few times and she always just stares at me disapprovingly. I feel so self-conscious every time I see her, she always looks me up and down frowning.”
Noted, my level of anxiety skyrocketing at the prospect of being on the receiving end of a fashion don’t. She’s notorious for her unyielding critics, but I hadn’t figured it transferred off glossy print pages to pedestrians. The Devil Wears Prada scene where Meryl Streep drags Anne Hathaway (over a cerulean sweater) was a real moment for Kelsey, a look saying it all. The scars remain, heard in her intonation as she told the story.

One.
The first time I saw Anna Wintour I was heading over to Melvin’s Cafe from the main restaurant, Miss Lily’s. There she was standing on the sidewalk as I walked in her direction. Wearing a white floral dress and signature shades. Rocking one dangling gold double triangular earring, a maroon skirt with slits on both sides, and a sleeveless black and white vertical striped shirt, that buttoned downed to tie at the bottom, a gold necklace, that had pendulum shaped pieces hanging, I freak out internally. Upon seeing me she moves back in surprise. It was a wordless exchange, her face conveying shock. Not only because she approved of my look, from bantu knots to heeled booties, but that I worked at such an establishment. Unable to control my facial expressions my eyes widen with joy. A sign of the future friendship I always imagined.
Pulling the door to enter Melvin’s, I take one last look in case I never get the chance again. A man exits his vehicle, handing her a package. Taking it, she enters her townhouse.
“OMG,” I screech seeing Kelsey behind the juice bar counter, “I just saw Anna Wintour!”
“You did? Told you. Did she give you a disgusted look?”
“NO! She liked my outfit!!”
“Oh, wow,” Kelsey says disheartened. In all fairness Kelsey in her Hawaiian shirts, loose fitting clothes and plain face made no effort, which is part of why she was relegated to the cafe as a cashier. She didn’t have the look, sexy, colorful, skimpy, to be a server at Miss Lily’s; the hierarchy was real. Despite not seeing eye to eye, the owners and Anna agreed on Kelsey’s ranking.

Two.
I’m in a rush. Although my tardiness had no consequences, I hate being even close to late. However, I ran out of eyeliner as I was about to start my second lid! Meaning I had to make a pitstop at CVS, where the line was too damn long. It’s the dead of winter, the sidewalks are runways with room for only one person to walk at a time. A strip of dry pavement is exposed, both sides covered by frozen, mounted snow and garbage. Lo and behold, as I’m about to traverse this obstacle course, Anna Wintour is pacing back and forth at the end of this makeshift runway. As if breaking in these over the thigh, leather, heeled boots weren’t enough, I have to walk for Anna without busting my ass. Not only would I be humiliated, I’d have to walk pass her afterwards.
Pairing another floral dress with a white jacket, cellphone to ear, shades on, Anna senses me and what does she do? She fucking stops to judge. Standing at the almost end of this runway, she faces me. Glaring. My heart literally seizes, then pounds against my ribcage. Is this the real life? Is this just fantasy? Only. Fucking. Me. Thanking God for throwing on my oversized Chloé sunglasses on a sunless day (had she seen my uneven eye makeup I’d be mortified), I walk, having no choice.
Balmain fur over a red dress that connects in the front, with a cutout back and sides, I catwalk for her eyes only. She stares. Starts to smile. Catches herself. Goes back to stoic. Then as a gesture of her approval, she makes room for me to get by, sans stepping on piled snow. Had I failed she would not have done so. This is a moment I’ll cherish forever. An actual highlight of my life, unlike some, I didn’t have to pay a million bucks for Anna’s validation (hi Kanye).

Three.
Halloween 2019. I finally left the apartment Genc Jakupi setup to have me spied on. I hated everyone there, especially lying, delusional, talentless Mallory, the girl I sublet from. His former The Box employee. Mallory who got us temporarily evicted, spending our rent money on a music video she made for Youtube. Had I not gotten word, we would have come home to locked doors the next day. She owed $5000. I made it so we could take what we needed while the issue was resolved. I digress.
Celebrating the thinning veil, Nani and I are dressed up. She’s an angel and I’m Dominque Deveraux. A wig, a skin tight, cream dress, backless, braless, a crossed string drawing attention to my spine. Walking down the street I see a woman dressed as Anna.
“Yes bitch, you’re Anna Wintour! You look major honey, major down to the bob. Work bitch, workkkkkk, yasss. You nailed it!”
The woman laughs, gripping my arm and tells me, “You look beautiful, absolutely beautiful,” she squeezes my arm while appraising me.
“See Anna I told you going out would be fun,” a scantily clad brunette says emerging from their shared cab, a blonde lady following behind her.
“Wait what! OMG you’re actually Anna Wintour!!! Omg stop!!!! I can’t!”
My eyes are bulging in pure disbelief. She’s literally wearing a bobbed wig, dressed up as herself. The color two fractions lighter than her own, her attire a dress and a dark caramel coat. She touches me a few more times, laughing her ass off before entering Indochine. Third times a charm, we were meant to be.

So I thought. Now I realize she tokenizes us, or is she just evil? Meeting her in person, meeting her standards, then seeing her allow the gutter rats known as the Kardashian Jenner West family to lower her standards. A family built on sex tapes, black magic, lies, an empire made of cards, no talent, no style, Kanye paid for her to care. To hear and experience her racism…there’s a great chasm between the two and I’m trying to fill the void.
Wasn’t L’wren Scott your friend? Why were you aiding big faced, small brained, ungrateful, mediocre, jail and hell bound Georgia May Jagger?
All I know is it’ll be handled accordingly. I’ll love those moments forever, then again I adored all the people who are now enemies. Via: Miss Lily’s