Shepherd, who parted ways professionally with Kim last fall, joined the reality star and her sisters Kourtney Kardashian and Kendall Jenner to attend the CFDA Fashion Awards in New York City this week, where Kim was honored with the Influencer Award.
Kim, 37, documented the trip on social media, sharing a snap of the crew abroad their private jet while flying out from Los Angeles.
Shepherd was also spotted arriving at the event on Monday night alongside Kourtney, 39, and spent the rest of the evening with the sisters.
She later shared a photo of her and Kourtney alongside family friend Simon Huck, captioning it: “getting the band back together.”
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Shepherd and Kourtney have spent plenty of time together since then, including a night out in the city on Tuesday.
“Date night,” Kourtney captioned a photo of her, Shepherd and Huck at the Polo Bar in Manhattan.
Prior to the trip, PEOPLE caught up with Shepherd at Shiseido’s summer kick-off event in Malibu, where she confirmed she’s still close with the Keeping Up with the Kardashians stars.
“Kim and the family are dear friends,” she said Sunday.
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She joined Kim’s team in 2013, but Shepherd and the star went their separate ways in November. At the time, a source said the decision was made after Shepherd wanted to transition into a larger role in Kim’s businesses and it didn’t work out.
“Kim gave her the chance but after a short period of time it became clear that Stephanie just didn’t have the knowledge to take on a role like that,” said the source. “Kim made an executive decision to part ways.” (Shepherd was made COO of Kardashian West Brands in 2016.)
Another source told PEOPLE the lines between business and pleasure had been blurred.
“Steph was very friendly with Kim’s family — she was almost part of the family,” explained the insider, noting that Shepherd had become particularly close with Kourtney in recent months.
“Kim needed an assistant where the relationship is more professional,” said the source. “It’s very difficult to work with friends, so Kim decided to hire someone else. The bottom line is that Steph was hired as an assistant, and Kim wanted to keep it like that.”
Although sources told PEOPLE the pair were no longer talking at the time, they’ve gradually grown close again. Shepherd celebrated Kourtney’s 39th birthday with the family in April and has remained supportive of Kim’s businesses, including her recent fragrance launch.