Winter 2020 Trends: It’s Time to Develop Your Personal Style Practice

Plus: the key to getting Leonardo DiCaprio's Après-Ski Freak Look; starting a great works book club; and other major trends.
A collage of lil uzi vert young thug leonardo dicaprio and two paintings
Getty Images (2); Backgrid; Getty Images (3) / Photo Collage by Gabe Conte

The changing of the seasons is like a big gong alerting us to a whole new universe of stuff that is cool. So what does the earth’s oblique angle to the sun have in store for us this coming year?

Developing a Personal Style Practice

Looking back on the last decade of...whatever that was, it is clear that 2010s fashion was all about the potent expression of personal style, from Jonah Hill’s streetwear shopaholic attitude, to Lil Uzi Vert’s Fitasia, to Shia LaBeouf’s outdoorsy influencerenza, to Harry Styles’s (I LOVE YOU, MAN!!!) sleazy glamour. They taught us to love fashion—and love ourselves in it—by going where few men had gone before.

This winter, as we are driven indoors by frigid temps and the collective sadness that is available in sizes from light malaise to full-on seasonal depression, we will turn this sense of daring inward for the Development of a Personal Style Practice, a movement that is all about using garments to express the innermost self you’ve found through your therapist or preferred meditation app.

The cultural moment demands we defend ourselves before we even know the charge, and for that reason it is more vital than ever that you:

  1. Look deeply in the mirror at the outfits you love, uttering to yourself words of affirmation and joy;
  2. Journal about brands and silhouettes and materials that dazzle you; and
  3. Spend more time looking without buying.

Assembling outfits—the private process that is usually eclipsed in our minds by the triumphal sharing of the fit pic—is a crucial part of the practice. You might want to light incense in the morning and chant a little “fashion is passion” mantra before you get things going; perhaps you need to put on Enya, or Dire Straits, or Lil Kim. Finally, you must develop eccentricities and signatures as a kind of habit. I recently met a friend for coffee who was carrying a giant Longchamp bag over his shoulder. I recently have admired the way Harry Styles and Evan Mock paint their own nails. I recently saw my friend Sam wearing a little silver swan pin on his lapel, and my other friend Nancy Pelosi wearing that golden mace pin on her black suit, and I thought, Absolutely.

Here’s the Winter 2020 Trend Report Guarantee: make style a pursuit, a practice, and a hobby, and you will win friends, and influence people.

Not Merely Looking at Art—But Gazing

If there’s one thing I learned from Yayoi Kusama’s “oh my god it’s art but I’m in it” rooms and the sexy banana that took Art Basel Miami Beach, it’s that people love art!!! Some people get really mad about Instagramming art and that’s totally fine but I actually don’t care. What I do care about is that people are no longer just in it for the selfie but in it to linger. Think of how long people stood in front of that banana!

By late February of 2020, people will be standing in front of paintings and sculptures for an average of 5-8 seconds longer, waiting for someone to eat it, or just taking things in with more pathos. It’s a luxury that the most famous painting in the world—the “Mona Lisa,” you bonehead—can no longer offer us, and it’s the kind of looking that the Museum of Modern Art’s rehanging, with its provocative comparisons and mercurial approach to the canon of art, anticipates. Especially rich for this experience are European painting galleries, where things are epic in scale. A lot to take in!

Hats

A dove-gray Stetson. A slate-colored astrakhan. An ill-cared-for fedora. Let Celebrated Hat God Brad Pitt be your guide; just go try on a ton of hats and see what works. (Great for your Personal Style Practice!) And as they tell you in those Wendy’s commercials, do what tastes right.

Reading the Great Books With Your Boys

Every woman I know is in some really chic book club, including Kendall Jenner, whom I have never met in person but feel I do know quite well because we have been reading all the same books lately.

This winter, countless men will (or could?) gather in groups large and small to read the great books. Moby Dick. Anna Karenina. House of Mirth! Aim high knowing you might finish the book but it’s really all about the journey. It is something in the spirit of Vladimir Nabokov teaching at Cornell, where it has long been rumored that his class was a favorite among jocks who needed to pad their schedule with an Easy-A class. (In truth, it was that his wife, Véra, did all the work.)

I am aware, for example, of two groups of men who have been making their way through Proust over the past two years, gathering semi-regularly in apartments across their respective cities and dunking madeleines (aww) in cognac (sure) as a sort of competitive sport of intellectual nostalgia. And that, as they say, is the vibe!

The Great Fur Coat Reckoning of 2020

Everyone is talking about sustainability, and what I expect in the next several months is a conversation about whether faux fur—which is plastic!—is more environmentally sound than the real deal.

Après-Ski Freak Looks

Longtime subscribers to the Prophet Pizza Trend Report will recall that the October 2018 edition predicted the hegemony of “APRÈS SKI FREAK LOOKS.” Now more than ever, this precognition is coming absolutely to life, with Leonardo diCaprio just this week eating French fries in Aspen wearing a black hoodie—hood up!—under a leather chore coat, with black pleat-front trousers and big hiking boots. This is the Après-Ski Freak Look par excellence, a passionate and highly personal combination of clothing designed for a rich person sport and clothing you wear everyday like a security blanket, for that “thank God I’m done barrelling down that freezing hill and can finally relax!” mystique. But you don’t have to be on the slopes to Freak the Après-Ski lifestyle: put a turtleneck with Ugg boots; pair ski pants with a T-shirt; wear ski goggles instead of sunglasses. Wear long johns!! With your most beautiful overcoat!!!

Leonardo DiCaprio nails the Apres Ski Freak look.EVGA, NGRE

This is going to be your dopest winter yet.