What I Learned About Style From Jennifer Lopez's “Feelin’ So Good”

The year was 1999, Y2K was fast approaching, Fred Durst had done it all for the Nookie, and as the Willenium drew near, some of us began to trade rock and/or roll for the best top 40 ever written. Meanwhile, actors and actresses pursued singing careers without fear of blog culture—and singers and musicians pursued acting careers because at this point, why wouldn’t they.

To put it plainly, it was Jennifer Lopez’s world, and we were just living in it.

Two years earlier, we’d seen her famous turn as Selena for a biopic of the same name, while the year also delivered Anaconda, a movie that we now know would’ve been better with the presence of a Nicki Minaj lyric. 1999, however, gave us J Lo.

Now officially, we met J Lo and/or the Artist-Formerly-Known-As-Jennifer Lopez in 2001 when her sophomore album was released. But the turn of the century laid the groundwork for the J Lo dynasty: circa 99, she was in the midst of a highly publicized relationship with then-Sean Combs, a music career the likes of which we can only dream, and a unique albeit glamorous sense of style. We—yes, you included—wanted to be her. And there are photos of us all wearing sparkly belts with skinny flared jeans at the bottom of all of our closets and drawers that prove my thesis perfectly.

And in the years before Grammy dresses and Bennifer (or more accurately, Internet culture), artists like J Lo had only her music videos to cultivate a very specific sense of self. In her debut single, “If You Had My Love,” she tapped into the futuristic world of blogs, webcams, and the idea of exhibitionism, but she also used her pieces to create a story. (Dance clothes looked athletic, while “oh, are you watching me?” scenes called for a bikini top.) In fact, her clothes have always helped tell the story, but none of those stories were nearly as interesting as the one she told in 1999’s “Feelin’ So Good.”

Here’s what I learned about style from the video I like to call, “The Most Productive Day Ever.”

TRUE DIVAS SLEEP WITH THEIR JEWELRY ON AND THEIR HAIR DID
Do you roll into bed wearing peasant garb like boxer shorts or a free t-shirt you got a bar once? (Yes.) Do you take off your jewelry before slipping into a coma, at no point considering leaving your bangles on? (Duh.) Do you sleep with makeup on? (I mean…) Too late: any morning could be the one where you’re forced to film a music video about your busy-ass day. Sleep like a winner—and winners don’t remove their gold for anybody.

IF JENNIFER LOPEZ CAN WEAR OVERSIZED BOOTS, WE CAN TOO
Would Jennifer Lopez wear Timbalands or work boots or Doc Martens or any oversized shoe style in 2014? Absolutely not—but guess what: 2014 isn’t in. 1999 is in (at least to me, right now, as I re-visit the Productive Day anthem of my youth). So look at how well these boots compliment the $20 she found on the ground; the way they contrast her dark pants and that beautiful autumn lighting. Business? She means it. But not as much as her hair clips and puffy coat do, which are basically my religion: welcome. (Namaste.)

ALL OF US WERE RIGHT ABOUT STYLE CHOICES AS KIDS AND TEENS
It’s a BLOWOUT SALE, motherfuckers. And do you want to try this fact on for size? There’s no way she would’ve found said sale if not for her oversized hairclips and big puffy jacket. We were right to covet that shit during the last years of middle school. Girlfriend is looking practical. She has shit to do. Do you know what she doesn’t have time for? Having hair fall in her face, being cold, and/or overpriced clothing. Life is a blowout sale and damn it, she just cleaned up. (Seriously though: she’s dressed very appropriately for the weather. Hand this photo to any person who doubts the importance of a big puffy coat.)

IT'S ACTUALLY WEIRD IF YOU'RE NOT WEARING A CHOKER
In this day and age, you can take your “hot or not” lists and you can burn them with the outdated hair straightener Jennifer Lopez is using to burn her stick-straight hair in this scene. Real women wear chokers. Real teens wear chokers. Real people (yeah, so take that holograms) wear chokers. Chokers say, “Fuck your necklaces” and chokers with crosses say (as seen here), “Yeah, I’ve seen The Craft.” Seeing The Craft is obviously something we all should be bragging about, so I think it’s safe to assume that is exactly the sentiment behind Jen’s “getting ready” look. Personally, I’m bragging about seeing The Craft as we speak.

IF YOU'RE GOING TO DANCE IN THE STREET, MAKE SURE YOUR FRIENDS ARE EQUALLY WELL-ACCESSORIZED
Here is a horrible screencap – they’re dancing so fast! – of the coolest-looking people in the world. Jen is wearing a fur coat, leather pants, and a choker. Friend to the left is in all her vinyl glory. Friend to the right put Jen’s earlier puffy coat to shame because it is Friday (or Saturday) night and it’s no time to fuck around. I am 100% sure this is how Jennifer Lopez commutes to and arrives at all of her social functions.

WEATHER-APPROPRIATE STYLE IS FASHION-FORWARD
And I know I’m technically repeating myself, but I care about you, and if ever there was an infomercial for “It’s cold outside, bring a jacket!” it is absolutely this song, this video, and the guy with his modern earmuffs on. I want to be all of them. (Warm. I am underdressed for the weather right now.)

YOU CAN WEAR BOOTS AND/OR FLATS TO THE CLUB
This is the look of a woman who has no fucks to give you, because even in 1999 she knew metallics were timeless. This is the look of a woman who will be sleeping in her jewelry tonight, thanks, and has never had a blister in her life thanks to a lifetime supply of Timbaland. This, friends, is a woman whose entire music video premise was, “Be productive and practical!” and sponsored by coats. This is why my friends and I would put this video on in grade nine before going to run errands. Because damn it, we wanted to find $20 on the ground, too.

Anne T. Donahue reaps the benefit of these style lessons everyday. She's on Twitter - @annetdonahue.