My favorite kind of vintage purchase is one that comes with a rich history. Take the Zac Posen dress I found at last year’s Vogue Vintage Market, worn by Laura Love to her prom in the late aughts, when Posen himself was still a fledgling designer. Or the copper belt my grandmother wore to her wedding brunch in 1953, cinched over a white lace dress, as was the fashion at the time. Then, there’s the 1980s Bill Blass gown I thrifted that I later discovered had once swept up the steps of the Met Gala on Pat Buckley in 1995—back when she was hosting the evening. These are the pieces that stay with me, and they are why Natalie Bloomingdale and myself are relaunching The SIL on March 3. Short for Stuff I Love, The SIL is a vintage site that highlights the women, and the stories, behind their iconic wardrobes.
We’re currently in a thrilling moment for vintage. The resale market isn’t just booming—it’s reshaping how we shop. According to McKinsey’s most recent State of Fashion report, secondhand and resale are projected to grow two to three times faster than the broader global apparel market in the coming years.
The internet has made finding coveted pieces easier than ever, too. We can source archival Prada or a ’90s Helmut Lang blazer from our phones at midnight. But as the market has become more abundant, something subtle has shifted. Descriptions have grown shorter. A dress is just a SKU. A coat is now a thumbnail, dislocated from any unique backstory. The online vintage shopping process has lost its former charm. That’s where we want to come in.
Natalie first launched The SIL in 2017 as a destination for hard-to-find independent pieces she personally sourced. More recently, she built a devoted following selling vintage furs on Instagram—one-of-one pieces that appeared, were snapped up, and moved on to their next chapter. Her audience embraced that rhythm of discovery; to date, she’s rehoused more than 3,000 coats and counting.
With The SIL’s relaunch, we’re working together to bring character back to vintage shopping. We’re opening up the closets of some of today’s most stylish women, allowing customers to shop directly from their personal collections. Structured as a series of online trunk shows, each Closet Feature will run for a set period before rotating to the next. We’re essentially focusing our merchandising philosophy on the stuff they love (but are ready to part with) and passing along their memories to the next person.
Each person fills out an in-depth questionnaire—part oral history, part memory exercise. We ask what was happening in their life when they wore the piece, whether anyone photographed them in it, whether they remember the weather, the music, the company. We interview, we fact-check, we go down rabbit holes. It’s detective work, yes, but it’s also a lost art of storytelling.
First up is Dee Ocleppo Hilfiger—founder of her namesake shoe line, creative director of Judith Leiber, and, yes, wife to Tommy. After relocating from Connecticut to perma-sunny Florida, she found herself with far less need for outerwear. She’s parting with a series of coats, including a 1970s Sant’Angelo for Robert Sidney piece she remembers Bill Cunningham photographing her in at a fashion show, as well as a hot pink coat she wore to a Breast Cancer Research Foundation luncheon by the label T. Jones. What is T. Jones, you might ask?
As vintage obsessives, Natalie (who happens to be the granddaughter-in-law of legendary clotheshorse Betsy Bloomingdale) and I (who once catalogued garments for the Costume Institute before becoming an editor here at Vogue) are researching, contextualizing, and annotating each piece up for sale. We’re pulling runway images, sourcing archival clippings, and revisiting contemporaneous coverage. T. Jones, for instance, was featured prominently in the late-1960s pages of Vogue and profiled in The New York Times in 1966 for its pragmatic retail philosophy: no sales, no markdowns. A pink coat goes from a fun find to a small part of fashion’s history.
Other upcoming SIL closets reflect a cross-generational spectrum of women whose wardrobes mirror distinct, accomplished lives. Amy Fine Collins—the grande dame Vanity Fair editor and raconteur—will offer pieces including the Fendi aviators she wore while learning to drive on a racetrack, a chapter she chronicled in her 2004 memoir The God of Driving. Natalie Steen, founder of the popular shopping Instagram The Nat Note, is contributing a Carolina Herrera jacket she rescued from her mother-in-law’s closet, and we traced it back to Herrera’s Fall 1990 runway. Roya Shanks, the fashionable fixture of Tribeca’s Odeon and this year’s Vogue Best Dressed honoree, is parting with pieces gifted to her by a devoted patron who recognized her love of fashion history. Meanwhile, designer and tastemaker Bunny Williams is contributing a jacket she wore to the Architectural Digest centennial celebration in 2020.
When it comes to The SIL’s women, we’re not scouting for Instagram clout or algorithmic fame. We’re looking for women with a point of view, ones whose lives are visible in their wardrobes. We’re finding them the old-fashioned way: through relationships, Rolodexes, conversations, observation. I’d always admired Dee’s style and when Natalie and I rang her up with nothing but a concept, she immediately FaceTimed us from her closet to showcase the vintage she could offer—but not before recommending some other women we could consider.
Natalie and I are constantly sending Instagram profiles to each other at all hours (like “She’d be perfect!” or “Do you know anyone who knows her??”), but even more thrilling is when women refer their friends to us. We’ve been so humbled to receive such support and enthusiasm for what we’re doing. Plus, each participant also selects a charity to receive a portion of the proceeds from her sale, adding intention to what might otherwise be a simple transaction.
Today, Dee’s closet will launch, with proceeds supporting Next for Autism. Even if you don’t shop, we hope The SIL becomes a place of discovery—not just of the women behind each wardrobe, but of the labels that once shaped fashion’s popular culture and deserve to be remembered. While much of the resale market assigns value based on what’s trending (now, it’s Tom Ford for Gucci and Carolyn Bessette–era Prada) we assign it differently. At The SIL, we have a more sentimental approach; here, every purchase is, in its own way, an inheritance.
