Why Don’t You...Fall in Love with Fashion?

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For the month of October, Bazaar will be celebrating our obsessions—how they delight us, connect us, and keep us going. Tune in each day for a new story, or go here to read them all.

Diana Vreeland had a singular take on not only fashion but life. Her eccentricity has become folklore and was best exemplified in an illustrated column of irreverent advice for chic living she called “Why Don’t You?” Resurrected and reimagined for modern life, the column, now written by Bazaar’s executive digital director, Lynette Nylander, will dispense tips on how to live stylishly, decadently, and daringly.

It’s always good to be obsessed with something. A solid fixation can give a life fabulous purpose! For our Obsessions issue, Lynette Nylander gathered some of our favorite style insiders to divulge the collection, the item, and the moment that made them hopelessly devoted to fashion.

WHY DON’T YOU … GET SPECIFIC

about your references. The year 1997 was pivotal for fashion, so replete with mind-bending design and seminal collections that Paris’s Palais Galliera recently devoted a whole exhibition to it, dubbing it “1997 Fashion Big Bang”! And it was Tom Ford’s spring collection for Gucci for that year that photographer and documentarian Tommy Ton cites as the moment he fell in love with fashion. “Nothing will ever be as clear,” he says. “My sister was away and asked me to record Fashion TV, hosted by Jeanne Beker, and there was a segment on Gucci’s Spring ’97 collection. Chandra North sauntered down the runway with smoky black eyes and wet hair, and it was love at first sight. Then Tom Ford came on screen and spoke so eloquently, and I was immediately seduced. That was the moment I wanted to work in fashion, and I would cycle to the library and rip out magazine clippings and plaster them to the wall.” What’s to learn from Tommy’s story? Don’t discount your obsession. It may become your meal ticket!

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Chandra North modeling in Gucci’s Spring 1997 show, designed by Tom Ford.

WHY DON’T YOU … TURN

your desire into an irreplaceable archive. Alexander Fury is one of the world’s most important fashion collectors, with more than 3,000 ultrarare vintage fashion pieces that he loans to institutions such as London’s V&A Museum. Fury’s love of John Galliano, the cornerstone of his archive, began when he saw the designer’s Fall 1995 Dolores collection, with model Carla Bruni in an ivory dress with black inlaid carnations. “She was standing on the rooftops of Spain, and it was snowing, and it looked like no other fashion show I’d ever seen. I was completely fixated.” Fury now owns said dress, as well as 300 other Galliano pieces, including a 1996 blanket coat—the result of a furious eBay bidding war that turned out to be with Galliano himself, trying to acquire back one of his pieces. An unrivaled commitment to obsession.

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Carla Bruni in John Galliano’s Fall 1995 show

WHY DON’T YOU … LET

your childhood idol be your motivation. Liana Satenstein, writer and founder of Neverworns, a digital platform for “froth-at-the-mouth obsessions,” remembers the first time she saw Desperately Seeking Susan, exclaiming, “Love New York, love Madonna!” Her love of the Queen of Pop endures. Madonna is regularly interwoven into her Substack entries, with odes to her best style moments and love notes to her favorite music videos. She is even fitness motivation for Satenstein: “Her ‘Vogue’ VMA performance from 1990 rewired my brain. I watch it along with a live performance of ‘Get Together’ on repeat every morning while pumping on an exercise bike for 20 minutes.”

Frank Micelotta Archive

Madonna performing at the MTV Video Music Awards, 1990

WHY DON’T YOU … TRANSFORM

your analog obsession into a digital community. Instagram account Getty Images Fan Club is obsessing gone digital, treating its 110,000 followers to fashion and pop-culture images from a pre-iPhone era, when we relied on paparazzi shots and fashion editorials to tell us what to wear. Think grunge-era Mary-Kate Olsen, Foxy Brown in her heyday, and Kirsten Dunst at her It-girl best. The account’s founder, Saul Pereira, remembers when his hunger for celebrity iconography began. “It was watching the documentary Catwalk,” he says, referencing the 1995 Robert Leacock film trailing ’90s supermodels. “To me, hearing Naomi and Kate talk, you felt like you were transported behind the velvet rope. The world was no longer 2D. It became alive, and I instantly felt like some sort of fashion insider, even though none of my friends cared!” His work now is a reminder that you’ll find your tribe of people who are just as obsessed as you. It just may take time!

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Isaac Mizrahi’s Fall 1994 show

WHY DON’T YOU … MAKE

your passion a full-fledged career. The Every Outfit podcast, hosted by Chelsea Fairless and Lauren Garroni, is catnip for fashion obsessives. The duo mine the best of fashion’s past and present for hot takes and even hotter looks, and they maintain a preternatural knowledge of all things Sex and the City. After working for the likes of Nylon magazine and legendary downtown fashion store Vfiles, they realized they had the gift of gab. The aha moment that fashion was their thing came courtesy of the Isaac Mizrahi documentary Unzipped, which turned 30 last year. Fairless says, “It was very ’90s-does-’60s, the supermodels looked incredible in fun fur, and Sandra Bernhard sang Sylvester’s ‘Mighty Real’ on the soundtrack!” So incredible was Mizrahi’s Fall 1994 collection (chronicled in Unzipped) that a model, quoting legendary editor Polly Mellen, exclaimed in it, “Honey, you just made fashion history!”

This story appears in the October 2026 issue of Harper’s Bazaar.

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