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Episode 1: A Well-Orchestrated-Multi-Hyphenated Mayhem with Casscellina? Yes Please!

Sept 16, 2025

Join our host, senior style icon Theodora Krochman, former mental health professional, and entrepreneur and documentarian Melissa Pierce in this season opener as Chicago's creative underground gets its moment in the spotlight as multi-talented director, producer, and stylist Casscellina. Known for her ability to spot hidden talent and create compelling visual narratives, Casscellina represents a new breed of artists who refuse to be boxed into single categories. From styling decades-spanning fashion shows to penning crime family sagas, Casscellina embodies the entrepreneurial creative spirit that drives Chicago's alternative arts scene.

The discussion explores how creative disciplines intersect and inform each other, particularly as Casscellina transitions from visual storytelling to written narrative with her upcoming three-part crime fiction series "No Questions Asked." Her insights into fashion's evolution across the 70s, 80s, and 90s, combined with her observations about society's increasing casualization, offer both historical perspective and contemporary cultural commentary. This episode reveals how one artist's diverse skill set reflects the broader changes in how we create, consume, and present ourselves in modern culture.

Follow Casscellina at @Casscellina, and @antixartshow

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 2: Welcome to Style it or Pile it!

Sept 23, 2025

In the second episode of our third season, senior style icon Theodora Krochman, and entrepreneur and documentarian Melissa Pierce introduce a new show feature, "Style it or Pile it," where we each take turns pulling something beloved but long left unworn from our closets to ask each other and you - do we move it into this season's rotation or do we move on?

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 3: Marquan Jones - Building Community in Food Deserts and Chicago Fashion

Sept 30, 2025

In the third episode of our third season, senior style icon Theodora Krochman, and entrepreneur and documentarian Melissa Pierce interview Marquan Jones the president of the Chicago Fashion Coalition, an organization that works to position Chicago as a prominent global fashion hub. We talk about Chicago Fashion Week and all of the upcoming events that the Chicago Fashion Coalition has a hand in producing (find them here). But Marquan's vision for how we show up in the world is more than how Chicago turns out on the runway, he is also a dynamic community builder and brand strategist who merges technology, creativity, and social impact by serving as an Impact Officer for the World Economic Forum's Global Shapers Chicago. Marquan's journey through food deserts to Chicago fashion is one that will likely get you out of your seat and into action. 

Follow Marquan and the Chicago Fashion Coalition on Instagram: @chicagofashioncoalition

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 4: Why Don't We Dress in Airports Anymore?

October 7th, 2025

In the forth episode of our third season, senior style icon Theodora Krochman, and entrepreneur and documentarian Melissa Pierce talk about Melissa's recent business travels and the styling, or lack of styling happening in airports these days.

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 5: Demetra Arvanitis: A Lil' Drop of The Real Mc-Coy-ture

October 15th, 2025

In the fifth episode of our third season, senior style icon Theodora Krochman, and entrepreneur and documentarian Melissa Pierce speak with stylist, consignment luxury studio owner, and expert authenticator, Demeta Arvanitis, about how deep her passion for all things couture goes - folks, it goes pretty darn deep. Tune in to hear just how deep this FGI board member gets into the details. 

Follow Demeta on Instagram @styledbydemetra

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 6: Buddies: National Flag Fashion - Noble Novelty or No-no?

October 21st, 2025

In the sixth episode of our third season, senior style icon Theodora Krochman, and entrepreneur and documentarian Melissa Pierce discuss the pros and cons of wearing the flag - a touchy subject in today's political climate where every fashion statement is a political statement, but especially this one.

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 7: Cold Storage & Hot Pants: Preserving Fashion History with Jessica Pushor 

October 28th, 2025

Ever wondered what happens to fashion after it makes history? Jessica Pushor, who manages 50,000 pieces of clothing at the Chicago History Museum, takes us behind the velvet rope into one of the most fascinating jobs in fashion. From a European court dress that survived 250 years (and a 1925 rummage sale) to Emilio Pucci hot pants that won't fit on any mannequin, Jessica shares stories that will make you see museum collections in a whole new light. Her journey to this role is just as compelling, she got some of her best education working at Buffalo Exchange, learning what makes clothing worth saving by handling thousands of secondhand pieces and hearing the stories behind them.

In this episode, Jessica reveals the surprising challenges of costume curation: Why do Civil War shoes last longer than 1990s sneakers? How do you display a dress from the 1770s when you don't have the original undergarments? And what do you do when everyone wants to donate their grandmother's underwear? She also shares practical wisdom for vintage lovers and collectors, explaining when to invest in quality basics versus trendy pieces, and why that emotional connection to clothing makes fashion such a powerful way to interpret history. Whether you're fascinated by conservation techniques, vintage shopping, or just love a good fashion story, this conversation delivers.

Follow Jessica on Instagram @Jessica_pushor and learn more about Chicago's fashion history at @chicagomuseum

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 8: Buddies Too Cheap to be Seen in Public 

November 4th, 2025

In episode 8 Teddi and Melissa bring pieces from their wardrobe that they just can't seem to figure out and ask, "should we style it, or should we pile it?" They discover that some things, even when they fit beautifully are just too cheaply made to see the light of day.

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 9: Rock & Roll Heart, Ramen Noodle Budget: Katie De Luna' on Paying Your Dues & Staying True    

November 11th, 2025

In the 9th episode of season three, Teddi and Melissa speak with Katie De Luna, a Chicago-based freelance fashion stylist who brings an infectious energy and rock-and-roll aesthetic to everything she does. Katie shares how her upbringing surrounded by music directly influences her edgy, eclectic styling approach. The conversation takes an honest turn as Katie reveals the challenging financial realities of building a styling career, including the costs of pulling clothes, paying for dry cleaning, and transportation—all while many editorial opportunities remain unpaid collaborations. Despite these obstacles, Katie's passion shines through as she discusses the importance of tailoring, the power of mixing fashion eras, and her philosophy of spreading kindness through genuine compliments.

Follow Katie on Instagram @stylingbydeluna   

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 10: Buddies - Too Cheap to Be Seen In Public

November 18th, 2025

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 11: From Goblin-Esque to Gorgeous: 

Emma Lyons on Art, Fashion & Blurring Every Creative Line 

in the Name of Vulnerability 

November 25th, 2025

In the 11th episode of season 3, Teddi and Melissa interview Emma Lyons, the self-trained artist who dances on canvas to create both paintings and wearable fashion simultaneously. Emma shares her journey from professional nurse to full-time creative, explaining her revolutionary technique that merges dance, painting, and fashion into one emotional performance. The conversation explores her philosophy that "you are a work of art" and why we've entered "the tired era" of fashion where our collective exhaustion has made us afraid of the vulnerability that comes with dressing up and being truly seen. From champagne tasting better in evening gowns to why being critiqued is inevitable no matter what you wear, this episode is a rallying cry for authentic self-expression and the radical act of blurring every creative line.

Follow Emma on Instagram at @emmalyonsart

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 12: Are You Bo Peep or a Sheep? How Religion Controls What Women Wear

December 2nd, 2025

In the 12th episode of season 3, Teddi confesses to Melissa in their segment "Style It or Pile It" that she hasn't worn her pick for the show in eight years, sparking a hilarious debate about good eating clothes, closet hoarding, and why we keep items we'll never wear again. The conversation takes an unexpected turn when Teddi's guilty pleasure watching The Secret Lives of Mormon Wives leads to a deeper discussion about how religion has historically controlled women's fashion choices. From mandatory head coverings in Greek Orthodox and Catholic churches to the evolution of "magic underwear" in Mormon culture, they explore how declining church attendance forced religious institutions to relax their dress codes. Melissa shares her own experiences growing up Mormon while Teddi unpacks the hypocrisy of labeling women as either "holy" or "hookers" based on their clothing choices. This episode is part fashion confessional, part cultural commentary, and all about the judgment we face whether we dress up or dress down.

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Episode 13: "Portfolio Culture is a Scam" Producer and Former Model, Maxi Black, Speaks Candidly about Saving Fashion's Soul

December 9th, 2025

In the 13th episode of season 3, Teddi and Melissa sit down with Chicago fashion producer and former fashion model, Maxi Black, who's reimagining the entire industry model from the ground up at MM Productions. The conversation dives deep into why the "build your portfolio" mentality exploits creatives, how the pay-to-play model has infiltrated fashion shows, and why sponsorship and patronage might be the only sustainable path forward for emerging designers. They explore the stark reality that most fashion creatives in Chicago work multiple exhausting day jobs, leaving them depleted and unable to pursue their passion with full energy. The discussion takes a philosophical turn when they connect fashion to agency, vulnerability, and authenticity, asking why Americans have stopped dressing up and whether our collective exhaustion has made us afraid of choice itself. From decision fatigue caused by fast fashion overload to Teddi's hilarious $10 Shein disaster, this episode examines why quality over quantity matters and how upcycling and vintage shopping offer both novelty and sustainability. 

Follow Maxi at @maxiinoir and @mproductions.llc

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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Signing Off in Style: The Psychology of Themed Clothes (Series Finale)

December 16th, 2025

In the 14th episode and final installment of Why Don't We Dress for Dinner Anymore, Teddi and Melissa dive into the polarizing world of holiday themed clothing, starting with Teddi's genuinely ugly Christmas sweater complete with bells and strategic rips. They dissect why certain professions (teachers and HR professionals, anyone?) seem drawn to pumpkin sweatshirts, turkey earrings, and light-up ornament accessories, debating whether these festive displays signal "I'm safe and approachable" or "I'm secretly wild and crazy underneath my mild-mannered exterior." The conversation takes a hilarious turn when they blame the Von Trapp family for starting the matching pajamas trend, questioning what Instagram has done to our holiday authenticity and whether those perfectly orchestrated family photos in identical sleepwear represent genuine festivity or carefully manicured performances. In their Style It or Pile It segment, Melissa confronts a Thailand souvenir dress she hasn't worn in six years, leading to a discussion about vacation shopping mistakes and the pressure to upcycle versus just letting go. As Teddi and Melissa sign off for the final time, they reflect on the incredible journey of producing this show together and the joy it brought them to explore fashion, vulnerability, and why we stopped dressing up in America. Thank you to all our listeners for joining us on this adventure. Happy holidays, stay fashionable, and keep asking why!

Follow Teddi, Melissa, and the show on Instagram:⁠⁠⁠ ⁠@teddilovesfashion⁠⁠⁠⁠,⁠⁠⁠ ⁠@the.melissa.fierce⁠⁠⁠⁠,⁠⁠⁠ ⁠@getdressedfordinner⁠⁠⁠ 

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