For over a solid decade, we collectively watched Stacy London strategically dismantle women’s wardrobes as co-host of TLC’s long-running reality TV behemoth What Not to Wear. The beloved makeover show centered itself around a handful of style rules, but beneath its snappy and sparkly facade, it exposed the vulnerable and transformative power of change while opening the door to a more evolved sense of self through a closet revamp. 

When you first meet Sunny Ruffalo, what strikes you is the unmistakable suspicion that she is a “somebody.” With her tousled blonde mane, her slim gray wool blazer, her pristine Adidas Stan Smiths, and a level, assured voice, she exudes a stealthy glamour that makes her stand out, even in a stylish town crawling with stylish city weekenders like Narrowsburg, NY.

To cross paths with Stephanie Cavalli is a precious thing. She is one of those rare people who emanate the kind of lived-in beauty that instantly makes you feel as though she has a story to tell. There is an enviable self-assuredness to her— a comfort in her own skin that somehow manages to strike just the right balance of wise and carefree. Perhaps, it is her Italian Caribbean roots at play, or, maybe, she has just done enough to recognize the beauty that resides in the un-doneness. For most of her twenties, Cavalli traveled the globe as a fashion model. Today, she is a mother to two boys and a shopkeeper of a vintage clothing boutique in Callicoon. Though at first, these two lives seem in total opposition, it’s precisely in this ability to walk the line between the exotic and the familiar where Cavalli’s magic lies. She’s statuesque but warm, seasoned, but grounded, and she believes that there is just as much beauty to be had in a simpler life as in any other.

Marcia Gay Harden’s 2018 memoir opens with a passage from that quintessential figurehead of upstate folklore, Washington Irving, about Rip Van Winkle’s decades-long nap in the Catskill Mountains. The anecdote is a metaphor for Harden’s relationship with her mother, of time passing and memories lost, but also reminds us that the Oscar-winning actress is intimately familiar with the territory. Her own Catskills home is a supremely private property on Gossamer Lake in the Catskills, where Harden and her family had congregated and escaped to, canoed, gardened, and cooked together since 1997 when she and her former husband acquired the initial 150 acres and continued to snap up surrounding chunks of land to accrue the current 300-plus. 

These musings played in my mind as I meandered from Bovina, where I call home, to Stamford, where Remy Holwick has made hers. A quietly inspiring morning that pulled us closer to winter also brought me into conversation with Holwick, a multi-disciplinary artist, activist, and mother who has made a home here in the Catskills since 2022. We talked about her nomadic upbringing, the ways in which this town of 2,000 has inspired her career, and what it means to contribute to community in a meaningful way. 

Taylor Foster has moved through many worlds: first Miami, then New York City, and now the subtle expanse of Upstate New York. She began with pastry, slipped into modeling, and later built a small café called Heaven, a gathering place as much as a business. Today she lives in a cabin, where her attention has turned to holistic skincare. 

The supermodel, actor, film producer and native New Yorker has been a fashion industry darling virtually since birth. Leaving Greenwich Village behind for a full time life in Woodstock, NY, she tells us about challenging mainstream ideas and her Pursuit of Consciousness. 

Let’s start with the basics: Helena Christensen is a globally famous photographer and model, one of the “magnificent seven”—along with Linda Evangelista, Christy Turlington, Cindy Crawford, Naomi Campbell, Elle Macpherson, and Claudia Schiffer—who inspired the term “supermodel” in the 1990s.

An ideal day upstate for Francesca DiMattio includes the following: working on the land, sculpting in the studio, and going to Salvation Army. For the 36-year-old artist, whose large-scale paintings and ceramic sculptures conjure up a jumbled universe of patched shapes and textures, thrift stores and their potpourri of knickknacks, oddities, and secret histories have long influenced how she thinks about her own work.

Imagine your dream weekend in the Catskills. Then think what it would look like if you took that weekend and transformed it into a covetable lifestyle brand. This is the foundation of the Livingston Manor Fly Fishing Club, a membership-based community of like-minded souls dedicated to getting out in nature and enjoying it to the core.

The sun was at its peak when I pulled in to the eerily quiet town of Bovina and drove up the gravel driveway to Brushland Eating House on Main Street. The town itself, which boasts a mere population of 600, felt like an empty movie set patterned with antiquated charms.

Interviewing a seasoned interviewer is no easy feat, and Kim Taylor Bennett has already gotten a third of my life story out of me before I realize she has somehow gently switched up the spotlight. Her warm and naturally inquisitive presence is a defining characteristic of her long and layered career reporting on and working in the music industry, the footnotes of which are as fascinating and vibrant as she is.