After months of recording a podcast asking women to talk about an important outfit, Perrie sits down with her younger sister, Jenna, to talk about something she wore on a family vacation, an outfit that's still pivotal to this day. Jenna's story is universal—who among us hasn't had a parent force us to wear something as a kid that we didn't feel comfortable in? We hope you'll enjoy this special episode—our last of the season—and think about your own What I Wore When moments that have shaped you and your relationship to personal style.  Follow @jsamo and @jsamotin_ceramics on Instagram.

On this podcast, you’ve heard from a lot of familiar names, including actors, singers, and reality stars. Rose Kirk is a name you’re probably not familiar with. As the Chief Responsibility Officer at Verizon, she rose through the ranks of corporate America, as a woman in the 80’s and 90’s. This week, the executive sits down with Perrie to share what she wore during her first big job interview and how her style has evolved since, the challenges and benefits of being a woman in the C-suite, and what her big purchase was after she started making real money.

In case you're not familiar with Leah Van Dale, here's a quick primer: she's the former WWE SmackDown Women’s Champion, and her ring name is Carmella, a nod to all the strong "mob wives" that have informed her creatively. This week, Leah sits down with Perrie to talk about being a successful woman in the professional world of wrestling, her past as an NFL cheerleader, her new line of affordable wine, Capo Cagna, and more.     Follow @carmellawwe on Instagram and Twitter. Shop her Capo Cagna wines at capocagna.com.  

It's impossible to find a woman between the ages of 25 and 45 that doesn’t know every word to the song "Unwritten" (or at least to the chorus that starts with the catchy “feel the rain on your skin"). This week, the song's writer and artist, Natasha Bedingfield, sits down with Perrie to talk about what she wore while writing the Grammy-nominated tune, as well as what it means to be an authentic mother, why she hates wearing jeans, and her latest album, Roll With Me.   Follow @natashabedingfield on Instagram and @natashabdnfield on Twitter. Find her newest album, Roll With Me, wherever you get music.  

Hello, Emily Nussbaum! Emily is the television critic for the New Yorker, and in 2016 she won the Pulitzer Prize for criticism. In 2019, she released her first book, I Like to Watch: Arguing My Way Through the TV Revolution. This week, Emily sits down with Perrie to talk about what she wore during a pivotal job interview, ‘80s fashion, letting kids watch Twin Peaks, perspectives on Carrie Bradshaw, and more.   Follow @emilynussbaum on Instagram and Twitter. Shop Emily’s book, I Like to Watch: Arguing My Way Through the TV Revolution, in bookstores and online. 

The former lead singer of punk-rock band Gossip is a lot of things: a bonafide rock star, a designer, a style icon, a staunch advocate for LGBTQ+ rights and a self-describing “fat, feminist lesbian from Arkansas.” This week, Beth sits down with Perrie to talk about her love of Old Navy, whether fashion’s inclusivity movement is really pushing us forward, and whether she plans to delve back into plus-size design. Strap in: Beth is a true delight.  Follow @bethditto on Instagram and Twitter. Watch Beth on season 2 of Becoming a God In Central Florida on Showtime later this year. 

La La Anthony’s career has taken many turns, each of which have been pivotal. Starting out on the radio, she became a host of MTV’s TRL during the early 2000s, which morphed into hosting a handful of popular reality shows, which then turned into an impressive acting career, including a role in Starz’ critically-acclaimed drama Power. This week, Perrie talks to La La about why it matters what a character wears when they get killed off a popular show, her style as a teenager in the ‘90s, her perspective on money and personal style, and—of course—her memorable cameo on a 2003 episode of Sex and the City.    Follow @lala on Instagram and Twitter. Shop the La La Anthony Collection at lalaanthonycollection.com, and look for La La on season 3 of Showtime’s The Chi, which will premiere this summer.

If you're obsessed with the world of professional ballet, this one's for you: this week Perrie sits down with Tiler Peck, a principal dancer with the New York City Ballet Company who recently wrapped this year’s run as the Sugar Plum Fairy in The Nutcracker, one of the most iconic ballets ever staged. Tiler explains why putting on that particular costume was pivotal to her life, but also indulged (many) questions about the cutthroat pop culture representations of professional ballet dancers. She also talks about her love of shoes, her close relationship with fashion legend Valentino, and what the future might look like for the New York City Ballet, which faced some high-profile management changes in 2018.  Follow @tilerpeck on Instagram and Twitter.

Founded in 2010 by Alli Webb and her brother, Drybar’s concept is simple: no cuts, no color, just blowouts. In 2020, there are over 100 Drybar locations across the US and a robust line of styling products. This week, Alli sits down with Perrie to talk about raising millions for a female-centric business in front of boardrooms of men, as well as personal style and whether it changes as you make more money, divorce, body image, her new passion for wellness and self-care, and her unique perspective on wealth.    Follow @alliwebb on Instagram.

Seemingly spawned from a more glamorous era, chef Angie Mar is a force of nature. Under her careful, curated approach, the Beatrice Inn restaurant—a New York City institution—has gone from exclusive cool-kid nightspot to an grown-up den of decadence with outstanding, unapologetically over-the-top food. This week, Angie sits down with Perrie to talk about her gorgeous first book, Butcher and Beast, and shares the touching story behind the pink feathered Oscar de la Renta dress she chose for the cover. We also talk about being a woman in a notoriously competitive industry, her skincare secrets (hint: it involves beef), and her unwavering love of fashion.    Follow @angiekmar on Instagram and @chef_amar on Twitter, and shop Angie’s book, Butcher and Beast, in bookstores and online.    For more on this episode, visit glamour.com/whatiworewhen.

If you were addicted to MTV’s reality show Making the Band in the early 2000s, you’ll surely remember Laurieann Gibson, the tough-as nails choreographer who went above and beyond to make sure amateur talent did everything they could to land their dream job. This week, Laurieann sits down with Perrie to talk about her experience on that seminal show, becoming a 2019 judge on So You Think You Can Dance, and the $39.99 dress she wore to her first celebrity-filled party on Diddy’s yacht. Laurieann also sets the record straight about her infamous relationship with Lady Gaga, for whom she served as creative director until 2011 when they parted ways to much online speculation and fanfare.  For more on this episode, visit glamour.com/whatiworewhen. Follow @boomkack on Instagram and @iamlaurieanng on Twitter.

Jameela Jamil is an interesting character. She flawlessly plays a lovable narcissist on NBC’s The Good Place but she’s also carved out a space for herself as a social media vigilante, regularly calling out brands, celebrities, and reality stars for potentially problematic behavior, including the relentless promotion of diet teas and unrealistic body image. This week, Jameela is characteristically candid—including about her so-called beef with the Kardashians, her own struggles with disordered eating, spending all her money during her 20s on good food and Chanel, her love of online shopping, and the truly shocking thing she did to make sure she didn’t get fired from The Good Place.    For more on this episode, visit glamour.com/whatiworewhen.   Watch Jameela on The Good Place, and follow @jameelajamilofficial on Instagram, @jameelajamil on Twitter, and @i_weigh on both.  

Since joining Bravo’s The Real Housewives of Beverly Hills in 2016, Dorit Kemsley has become one of the most memorable women in the franchise thanks to her daring sense of style, outspoken personality, loyal family, and—yes—slightly ambiguous accent.   On this week’s episode, Dorit sits down with Perrie to talk about a long list of topics including how the cast chooses their outfits, motherhood, her rationale for buying clothes and shoes and bags well into the thousands of dollars, and why she feels that dressing for a man isn’t always such a terrible thing.    Follow @doritkemsley on Instagram and @doritkemsley1 on Twitter. Shop Dorit’s fashion line at www.beverlybeachbydorit.com, and watch her on The Real Housewives of Beverly Hills.

Sutton Foster is a quiet force: The Broadway superstar has been nominated for six Tony Awards (she’s won two) and for the past six seasons she’s been starring on Younger, the beloved TV Land series that has her playing both a 40-something and a millennial. This week, Sutton sits down with Perrie to talk about what she wore when she auditioned for that show, her favorite musical of all time, her complicated path to motherhood, her new Gucci loafers, and how in some ways, caring less about what you wear to auditions can be an asset.    For more on this episode, visit glamour.com/whatiworewhen. Follow @suttonlenore on Instagram and @sfosternyc on Twitter, and watch Sutton as Liza Miller on Younger.

Vanderpump Rules fans, this one’s for you tonight. No matter your opinion on the Bravo show’s queen bee Stassi Schroeder, it’s impossible to deny how unapologetically herself she is in everything she does. This episode is no different. Stassi sits down with Perrie to talk about being a ghost (on brand!), her upcoming wedding (though she was hyper-secretive about details), when your body becomes public conversation (it sucks), and which Vanderpump cast member is the most annoying on social media (Perrie had an answer.)  For more on this episode, visit glamour.com/whatiworewhen. Follow @stassischroeder on Instagram and @stassi on Twitter. Watch her on Vanderpump Rules. Visit stassischroeder.com for merch and tour dates. Listen to her podcast, “Straight Up with Stassi,” wherever you get podcasts, and find her best-seller, Next Level Basic: The Definitive Basic Bitch Handbook, in bookstores and online.

If you’re a podcast fan, you probably devoured Broken Harts, a serialized true crime story about The Hart Family that’s been downloaded more than 11 million times. The podcast stemmed from an investigative report former Glamour editor Justine Harman was working on. Now a freelance writer and podcaster—be on the lookout for her new audio series in January—Justine sits down with Perrie to talk about how fashion can play a role in a woman’s life during the worst circumstance a person can imagine, and why it isn’t always as simple as throwing on a black dress.    For more on this episode, visit glamour.com/whatiworewhen.   Justine Harman is a writer, podcaster, and Glamour contributor. Her new nonfiction podcast, The Baron of Botox, drops January 14, 2019. Follow her on Twitter @justineharman and on Instagram @justinedc.

Ilaria Urbinati is one of Hollywood’s most in-demand fashion stylists and her clients include The Rock, Donald Glover, Rami Malek, Joel Kinneman, Bradley Cooper, Chris Evans, Milo Ventimiglia, Armie Hammer, and more. Yep, all men. On this week’s episode, Ilaria—who was nine months pregnant with twins at the time—talks to Perrie about the differences between dressing famous males and females, why we’re all so obsessed with airport style, and the style mistake she made on her first big job with a ‘90s superstar.  For more on this episode, visit glamour.com/whatiworewhen.   Follow @ilariaurbinati on Instagram.

It's Tiffani Thiessen, you guys! Whether you had a crush on her as sweet cheerleader Kelly Kapowski on Saved by the Bell, devoured her every calculating move as Valerie Malone on Beverly Hills, 90210, watched her cook for celebrity friends on Dinner at Tiffani's, or are revisiting her with your kids on Netflix's charming Alexa & Katie, it's hard not to be in awe of how long the actor has been a pop culture presence. This week Tiffani sits down with Perrie to talk about the first time she truly felt like a movie star, what it's like literally growing up in front of America, how her style has changed since having two children, and the '90s fashion trend she single-handedly started.   For more on this episode, visit glamour.com/whatiworewhen. Follow @tiffanithiessen on Instagram and Twitter. Watch her as Lori Mendoza on Alexa & Katie on Netflix. Find Pull Up a Chair, her cookbook, and You’re Missing It, the children’s book she wrote with her husband, Brady Smith, in bookstores and online.  

Amanda Seales is busy. Among her many jobs: a stand-up comic, a scene-stealer on HBO’s Insecure, a podcast host, and an author of the new book Small Doses: Potent Truths for Everyday Use. This week Amanda showcases her signature honesty to talk with Perrie about what she wore when she first started performing onstage, Rolex watches, fast fashion, the shifting landscape for women in comedy, and the concept of real friends in today’s debatably authentic Instagram age.   For more on this episode, visit glamour.com/whatiworewhen.   Follow @amandaseales on Instagram and Twitter. Watch her as Tiffany on Insecure and in her stand-up special, I Be Knowin’, on HBO. Visit www.smartfunnyandblack.com for Amanda’s live-show tour. Listen to her podcast, Small Doses with Amanda Seales, wherever you get podcasts, and find her best-seller, Small Doses: Potent Truths for Everyday Use, in bookstores and online. 

Cook and author Alison Roman has become something of a champion for millennials who prefer hanging out over going out. Her unfussy approach to cooking—coupled with her highly authentic persona—landed her a food column in The New York Times, two successful cookbooks with two more on the way, and thousands of adoring Instagram followers. This week, Alison sits down with Perrie to talk about food, yes, but also personal style and the items she feels most comfortable wearing, the (very) expensive bag she’s dying for but can’t justify, and the outdated fashion “rule” nobody should follow. Alison and Perrie also get into dating deal-breakers, how her feelings about food and relationships can’t always be separated, and the thing she’ll never do on a first—or second—date.     For more on this episode, visit www.glamour.com/whatiworewhen   Find Alison Roman’s cookbooks, Nothing Fancy (a current New York Times bestseller) and Dining In, in bookstores and online, and look for her columns in Bon Appétit and The New York Times. Follow @alisoneroman on Instagram and Twitter.