Ally and Steve travel to Milk Studios in Chelsea, Manhattan to talk with powerhouse couple Zanna Roberts Rassi (fashion correspondent for E! News / senior fashion editor of Marie Claire) and Mazdack Rassi (fashion entrepreneur / co-founder of Milk Studios) to discuss how it all started, the current state of fashion and their newest venture together; Milk Makeup.

Nicole Will, an art adviser in New York (Will Art Advisory) brings Ally and Steve to three different shows in lower Manhattan to meet artists and discuss their work. Caris Reid, walks them through her show "Sub Rosa" at the Denny Gallery. Jess Johnson shows at the Jack Hanley gallery (where Ally experiences a trippy virtual reality experience). Lastly, they visit a showing of Karl Wirsum's work at the Derek Eller gallery.

Interior Designer, Martyn Lawrence Bullard, has decorated the homes of Cher, Christina Aguilara, the Osbournes, and the Kardashians. Martyn shares with Ally and Steve the craziest sex rooms he has ever designed and how he went from being a stage actor in England to one of America's top designers.

Steve and Ally sit in with Anya Hindmarch, an acclaimed handbag and accessories designer, in her London studio to talk about how her handbags are made, how she feeds her brain, and her hero, Margaret Thatcher.

Ally and Steve sit in with musician / photographer / activist extraordinaire Bryan Adams to talk about his creative process and his upcoming musical adaptation of an early 90s classic.

Ally and Steve travel to New York where Ally sits down for a candid conversation with her dad - fashion icon Tommy Hilfiger.

Timo Weiland, acclaimed fashion designer and chosen for the CFDA incubator program, discusses everything from how much fashion week and the industry in New York has changed, and how he transitioned from being a banker on Wall Street to an acclaimed fashion designer/DJ.

Pamela Love, an award winning jewelry designer based in New York City, talks about her obsession with Greek Mythology, and trying to keep up during New York Fashion week without her sleep monster getting in the way, and her apprenticeship with artist, Francesco Clemente.

Ally Hilfiger and Steve Hash sit in with creative director, Trey Laird, and discuss Marfa, Texas, his experiences working with Gigi Hadid, Tommy Hilfiger, Lady Gaga, Tom Ford, how he started his company, and his early days with Donna Karen. Then... Ally and Steve fly to London to sit in with Gigi Hadid to talk to her about working with Tommy Hilfiger, packing and dressing for your mood, what she likes about designing the Gigi X Tommy collections, and how hands on she is every step of the...

"Sit-In with Ally Hillfiger and Steve Hash" debuts Wednesday, October 18th, 2017.