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Second Life

Podcast Series Second Life

Hosted by Who What Wear co-founder Hillary Kerr, Second Life spotlights successful women who have made major career changes. Guests share lessons they've learned through fearlessly daring to pivot, and how they've used skills from their "first lives" to navigate their winding career journeys.

Series Episodes

The Who What Wear Podcast: WWW20 Presents: Chriselle Lim, the Internet's Original It Girl Playing

The Who What Wear Podcast: WWW20 Presents: Chriselle Lim, the Internet's Original It Girl

This month marks Who What Wear's 20th anniversary! To celebrate, we're spending all of October with guests who have left an indelible mark on the fashion-and-beauty world and grown up alongside us over the past two decades. To kick things off, Hillary sits down with Chriselle Lim, one of the original fashion content creators. Lim began her career as a fashion blogger and YouTuber in the late 2000s, and over time, she paved the way for creators like herself to become a respected part of the fashion industry. In this episode, she looks back on the last 20 years of her life and career, shares what it takes to have longevity as a creator, and explains how her dedication to storytelling in all forms has taken her from blogger to creator to founder and creative director of Phlur.  Watch this episode on our new YouTube channel, and be sure to subscribe!

42 mins

7 October Finished

Rickie De Sole: Editor of Air Mail's Dress Code Playing

Rickie De Sole: Editor of Air Mail's Dress Code

Rickie De Sole is the editor of Air Mail’s style-and-fashion publication, Dress Code. De Sole started her career as a fashion assistant at Vanity Fair. After that, she moved into public relations at Prada, where she worked from 2007 to 2010. De Sole then returned to the world of fashion media at Vogue as a market editor, working her way up to accessories director. After, De Sole went to W Magazine, eventually becoming the fashion director before transitioning back to Vogue. There, she eventually gained the title of executive fashion director of Vogue.com. De Sole later pivoted to retail at Nordstrom, ending her time there as the VP fashion director. Throughout her career, she has also served on the board of companies such as Rent the Runway and Vestiaire Collective. Today, she leads Air Mail’s style publication, Dress Code, and serves as a senior adviser at Sandbridge Capital.

57 mins

5 October Finished

The Who What Wear Podcast: Denim Consultant Benjamin Talley Smith Returns to Talk Fall Trends and the New Guest in Residence Denim Line Playing

The Who What Wear Podcast: Denim Consultant Benjamin Talley Smith Returns to Talk Fall Trends and the New Guest in Residence Denim Line

This week, Hillary sits down in studio with denim expert Benjamin Talley Smith. Talley Smith  is a denim designer and consultant who works with the designers at your favorite brands—such as Khaite, Reformation, and J.Crew—to develop their denim lines. Today, he's chatting all about the new denim line he worked on for Gigi Hadid's brand, Guest in Residence, and his top trend predictions to look out for this fall.  Watch this episode on our new YouTube channel⁠⁠⁠⁠, and be sure to subscribe!

29 mins

30 September Finished

Casey Lewis: Creator of After School Playing

Casey Lewis: Creator of After School

Casey Lewis is the creator of the Substack newsletter After School. However, before she was writing to an audience of tens of thousands, Lewis was writing about youth trends on her blog Teen Fashionista. Later on, she started at Teen Vogue as an intern, and over the course of her time there, she worked her way up to senior digital editor. She left Teen Vogue to create Clover Letter, a daily newsletter for teen girls, which gained traction quickly and eventually got acquired by AwesomenessTV. Lewis then transitioned to a senior editor role at New York magazine, but she missed writing. So in 2021, she put in her notice and started her youth-trend Substack publication, After School. Today, she continues to write her newsletter to dedicated readers, makes accompanying content on Instagram and TikTok, and uses her expertise in youth trends to consult businesses, from early-age startups to Fortune 500 companies. 

50 mins

28 September Finished

The Who What Wear Podcast: Designer Christian Cowan Unpacks His Buzzy NYFW S/S 27 Show Playing

The Who What Wear Podcast: Designer Christian Cowan Unpacks His Buzzy NYFW S/S 27 Show

This week, Hillary chats with designer Christian Cowan about his buzzy spring/summer 2027 collection and showing at New York Fashion Week. They discuss his biggest inspirations, the brand's evolution over the past few seasons, and the countless celebrities who can't get enough of his designs. Plus, he shares whether or not bridal is on the horizon.  Watch this episode on our new YouTube channel⁠⁠⁠⁠, and be sure to subscribe!

33 mins

23 September Finished

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