An XXL cashmere sweater for Noam Chomsky. A Goyard purse for Peggy Siegal. A Rolex for a redacted recipient.
Contained within the millions of files that the Justice Department has released related to the wealthy sex offender Jeffrey Epstein are hundreds of references to luxury labels. Mr. Epstein, it seems, had pointed opinions about style and how to deploy it. The many mentions of fashion form a textual trail on how Mr. Epstein, who died by suicide in federal custody in 2019, used gifts to ingratiate himself with famous friends and reward those in his orbit.
Time and again he showed his attention to detail in matters of fashion. In an August 2017 email, Mr. Epstein instructed a redacted recipient to “get Prada Handbag” for Masha Drokova, who worked as his publicist. Mr. Epstein subsequently approved a $1,790 black Prada tote (“perfect,” he wrote), and received a reply that it was sent via FedEx to Ms. Drokova the following day.
A year later, a series of emails detailed the purchase of 31 Sea Island cotton boxer shorts and 31 Sea Island cotton shirts, all size medium, from the Swiss luxury underwear brand Zimmerli — birthday gifts for Woody Allen totaling $9,858.
The gifts were not always extravagant, and in some cases they were damning in their banality. In June 2016, Mr. Epstein wrote to his girlfriend, Karyna Shuliak, to suggest ordering customized pullover and zip-up sweatshirts for a number of individuals including Valeria Chomsky, Mr. Chomsky’s wife, “Thiel” and “Ruemmler,” seeming references to Peter Thiel and Kathryn Ruemmler, general counsel of Goldman Sachs who appears frequently in the emails. In March 2018, Mr. Epstein again wrote Ms. Shuliak to order four X-Large zipper sweatshirts for Stephen K. Bannon.
It is not clear from the emails if any of these individuals received Mr. Epstein’s gifts. But the emails do shed light on how Mr. Epstein’s largess was received by some.
“Just got home from dinner to a beautiful Prada bag!!!” wrote Faith Kates, a co-founder of the modeling agency Next, who has since said she was retiring from the company after appearing in Mr. Epstein’s emails.
“Thank you For the beautiful birthday present,” she wrote to Mr. Epstein, “and most importantly for being my friend.”
“Shoes are very nice. thanks,” the author Michael Wolff wrote to Mr. Epstein in December 2018. “Am totally tricked out by Uncle Jeffrey today! Jeffrey boots, handbag, and watch!” Ms. Ruemmler wrote to Mr. Epstein in January 2019, about six months before Mr. Epstein was arrested and charged with sex trafficking by federal prosecutors.
Not all of Mr. Epstein’s presents were warmly received. In 2016, Soon-Yi Previn, the wife of Mr. Allen, thanked Mr. Epstein for “the sweatshirts,” but asked that next time they not be monogrammed: “so when I regift it no one will suspect.” Mr. Epstein advised that she could always regift them to someone with the same initials.
Among the crowd Mr. Epstein navigated, thank you notes signal good manners. In many of these emails, those notes also function as an acknowledgment of a transaction, and therefore an acquaintanceship.
Indeed, by the early 2010s Mr. Epstein had already served jail time on prostitution charges and was a registered sex offender, but that did not prevent the well-connected recipients of his gifts to shower him with gratitude and remain in close contact.
The emails paint a picture of a man calibrating presentability within the codes of upper-class American society. They also provide a snapshot of the subtle ways taste and style preferences are wielded within that community.
In January 2018, he wrote to Mr. Bannon advising him that “white shirts look better on you than blue,” punctuating the message with a smiley face emoticon. The advice didn’t seem to land: Mr. Bannon replied that he hadn’t worn a white shirt in 20 years.
Mr. Epstein was also willing to convey his distaste for what he considered the wrong attire. In a 2009 email, he chastised a redacted recipient for wearing “a disgusting t shirt and jeans” to a dinner.
Emails showed regular appointments for undisclosed or redacted individuals at Frederic Fekkai, an Upper East Side hair salon for well-heeled women. The frequency of such appointments eventually became a concern within Mr. Epstein’s circle. In May 2018, Lesley Groff, Mr. Epstein’s executive assistant, emailed a redacted group of recipients instructing them that “from now on Jeffrey would like you to please email me your request to go to Fekkai for any services.”
Mr. Epstein, and those for whom he bought gifts, favored easy polish over flash: cashmere, soft sweatshirts, lace less loafers. Name brands, when they appear are almost always of the “quiet luxury” category (which, before it was a hard-sold trend, was simply how one was expected to dress in places like the Upper East Side and 16th Arrondissement).
During the 2018 holiday season, Mr. Epstein, through assistants, purchased Apple Watches in New York and Paris as gifts. Emails showed, when given the option, recipients selected not just any Apple Watch, but an Hermès banded Apple Watch.
It is telling that when doling out gifts, Mr. Epstein choose the subdued, black Prada hand bag, not a trendy yellow or red one. Sparkle was reserved for diamonds and watches. This discernment was his way of showing that even though he was a son of Brooklyn who never graduated college, he had learned the proper codes and cues to ascend through this moneyed milieu. Those who received his gifts were often happy to help in that ascent.
Jacob Gallagher is a Times reporter covering fashion and style.
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