In this buddy episode, Teddi shares her exciting experience working with talented photographer Marcus Jenkins, highlighting his meticulous attention to lighting and composition that resulted in portrait-quality images she describes as "like paintings." She gives special recognition to designer Omaima Couture from Niles, who provided the stunning navy blue pleated gown she wore for the photoshoot. Teddi also mentions an upcoming project with photographer Skyye Kimmons for his "40 Over 40" series featuring women over forty, showcasing Chicago's vibrant creative community.

The conversation shifts to current fashion trends, with both hosts discussing the resurgence of 1970s style, specifically boho chic aesthetics with flowy blouses, wide-legged jeans, and platform shoes. Melissa, dressed in vibrant patterns and layered accessories, embodies this trend that Teddi notes is prominent in 2025 fashion. They explore how vintage shopping connects to these cyclical fashion trends, with Melissa sharing insights from her thrift shopping adventures with her teenage daughters and giving shoutouts to local vintage shops, including Dovetail in Wicker Park and Luvsick, which specializes in plus-size vintage clothing.

As the episode draws to a close, Teddi and Melissa celebrate their one-year podcast anniversary, recalling how they first met at last year's Curio spring mixer—the same event they had just attended. They reflect on their journey creating a podcast dedicated to showcasing Chicago fashion creatives and express gratitude to Curio for bringing them together.

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

People and places we love mentioned in the show:

@emjay_fotos

@aesthetic_by_skyye

@omaimacouture

@vintagefrills

@shopfleeky

@Luvsickplus

@Dovetailchicago

Join hosts Theodora Krochman and Melissa Pierce as they welcome Sharaun B, who shares her journey from America's Next Top Model (Cycle 11) to creating Model Tribe, a platform revolutionizing the modeling industry by combining fashion with wellness. Sharaun candidly discusses the reality behind reality TV, revealing how being eliminated for "having too much confidence" became a catalyst for her personal transformation and eventual mission to help others.

Through Model Tribe, Sharaun has created virtual and physical spaces where women of all ages learn modeling techniques while focusing on confidence-building and self-worth. She challenges traditional modeling industry toxicity by emphasizing the connection between fashion and mental health, declaring, "Fashion is wellness," and advocating for a more feminine, creative approach to personal style.

The conversation explores how modeling can serve as a tool for self-discovery rather than just a professional pursuit. Sharaun shares how her new headquarters at Chicago's Water Tower Place offers runway training, photoshoots, and wellness activities that help women connect with their bodies and develop authentic confidence that comes from embodiment rather than performance.

As the episode concludes, the three women contemplate why society has become so casually dressed. Sharaun offers insights on how systemic pressures and exhaustion lead to prioritizing comfort over self-expression. She presents her vision for breaking this cycle through celebrating individuality, reclaiming feminine energy, and creating supportive communities that encourage creative expression through fashion.

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

Follow Sharaun B: @sharaunb

Join hosts senior style icon and former mental health professional Theodora Krochman, and entrepreneur and documentarian Melissa Pierce on "Why Don't We Dress for Dinner Anymore?" as they examine fashion as a psychological and cultural phenomenon.

In Episode 13, Melissa shares exciting news about completing her MBA thesis, which examines how the absence of strategic planning sets small creative businesses back, creates poor workforce feedback loops, and keeps fashion brands trapped in survival mode. Drawing from her personal experience working in the fashion industry, Melissa describes the challenges of operating in environments where leadership fails to establish clear key performance indicators and collaborative decision-making processes. Teddi, drawing from her own marketing background in healthcare, provides contrasting examples of effective leadership practices that involve team members in budget decisions and strategic direction.

The conversation expands to explore the broader challenges facing creative professionals in the fashion industry, with both hosts noting how many talented designers and stylists in Chicago must maintain other careers while pursuing their passion part-time. They discuss the particular difficulty of monetizing artistic pursuits without compromising creative integrity, sharing personal examples from their families, including Teddi's husband Ken, a talented artist who spent years in the insurance industry to support their family despite his artistic talents. The hosts reflect on how economic necessities often force creative individuals to put artistic aspirations on hold.

As the episode wraps up, Teddi and Melissa contemplate the value of pursuing one's passion, even if later in life, highlighting how constraints of time, energy, and financial responsibilities can postpone creative pursuits. Their candid conversation offers listeners insight into the business realities of creative industries while celebrating the persistent drive that keeps artists and fashion professionals pursuing their vision despite institutional and economic challenges.

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

Join hosts senior style icon and former mental health professional Theodora Krochman, and entrepreneur and documentarian Melissa Pierce on "Why Don't We Dress for Dinner Anymore?" as they examine fashion as a psychological and cultural phenomenon.

In Episode 11, Teddi and Melissa dive into the emerging "Castle Core" trend that Pinterest has identified as a growing aesthetic pushing back against minimalism. The hosts explore how this medieval-inspired fashion movement—featuring armor elements, chainmail accessories, and medieval silhouettes—might reflect deeper societal anxieties and desires. Melissa theorizes that the trend represents people seeking a connection to pre-digital, pre-plastic times while simultaneously serving as psychological armor during uncertain times. Teddi notes her surprise at seeing friends like Nikki Street Style wearing actual armor pieces and Delphine (a Season 1 guest) wearing a hand-painted leather jacket resembling armor at recent Chicago fashion events.

The conversation expands to include observations about the return of fur on major fashion runways, with Teddi highlighting Fendi's recent collection featuring both shearling and faux fur. Drawing parallels to the 1930s, when society embraced glamour and luxury during difficult times, Teddi suggests today's fashion responds similarly to global uncertainty. She notes her recent purchases of a leopard faux fur coat and black faux fur shrug, unconsciously aligning with this trend toward a more expressive, luxurious dressing that contrasts with the previous "quiet luxury" aesthetic.

Throughout their discussion, Teddi and Melissa examine how fashion continues to function as both political expression and psychological comfort during turbulent times. Teddi concludes that focusing on personal style can be an act of resistance and self-care. As she puts it, "I'm going to dress for dinner. I'm going to make plans with my husband, and I'm going to get all dressed up. I'm not going to let that bastard bring me down."

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

Join hosts senior style icon and former mental health professional Theodora Krochman, and entrepreneur and documentarian Melissa Pierce on "Why Don't We Dress for Dinner Anymore?" as they examine fashion as a psychological and cultural phenomenon.

In Episode 10, Teddi and Melissa sit down with Sandra "Sandy" Silverman, author of "From Bullshit to Botox," for a candid exploration of beauty standards, aging, and fashion choices for women over 50. Sandy shares insights from her extensive personal journey with anti-aging interventions, having invested over $300,000 in cosmetic procedures and surgeries. The conversation takes a revealing turn as Sandy explains how her initial cosmetic procedures were driven by insecurity fostered by her soon-to-be ex-husband but how she has since reclaimed these choices as acts of personal empowerment and body autonomy.

The discussion moves beyond physical procedures to examine how fashion choices can either age a woman or help her appear more youthful. Sandy addresses perceived contradictions between her book's advice and her personal style choices, particularly regarding age-appropriate hemlines. Teddi and Melissa challenge Sandy on broader questions about beauty standards, exploring whether attractiveness is limited to youth or surgically enhanced maturity and how personal style evolves through different life stages.

Throughout this thought-provoking episode, the hosts and guest examine the complex psychological motivations behind anti-aging efforts, the cultural pressures facing women as they age, and how different fashion eras have influenced contemporary beauty ideals. Sandy's journey from making changes to please someone else to making choices that please herself offers listeners a powerful narrative about reclaiming personal agency in a youth-obsessed culture.

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

Follow Sandra @sandralenasilverman

Join hosts senior style icon and former mental health professional Theodora Krochman and entrepreneur and documentarian Melissa Pierce on "Why Don't We Dress for Dinner Anymore?" as they examine fashion as a psychological and cultural phenomenon.

In Episode 9, Teddi shares her immersion in Chicago's vibrant fashion scene throughout February, beginning with model Maxi Black's cinematic fashion show "The Cinema" featuring vintage styling by Vintage Frills. The conversation explores the dramatic evolution of clothing sizes across decades, with Teddi noting how her vintage Size 14 jacket (purchased directly from the runway) fits her modern Size 4 frame perfectly. Teddi describes her glamorous ensemble for the event - a borrowed Leen Gundogdu (Kivanci) black velvet off-shoulder dress with crinoline, complemented with period-appropriate accessories reflecting her appreciation for the 1930s-50s fashion aesthetics.

The discussion continues with Teddi's attendance at the FGI Blue Jacket fundraiser for prostate cancer research, which was MC’d by AJ Johnson and featured collections from Chicago designers Dana Asady and Raj Patel of Karmic Couture. Teddi recounts her serendipitous find at the Galentine's Day shopping event at 900 North Michigan, where she discovered perfectly fitting statement pants at an Azeeza sample sale! The episode also covers her participation in a promotional video for the founder of Why Not Petites (and Season 1 guest), Britney Wittes's, upcoming fashion event during Chicago Art Week, directed by Abe and produced by Chau, plus Teddi's upcoming fashion calendar including visits to bridal designer Omaima Abbes (Omaima Couture), an Anine Bing opening styled by Rachel Penca, and the Curio Mixer event that both hosts will attend.

Between fashion discussions, Teddi and Melissa engage in their characteristic banter about social media presence, the challenges of facial recognition, and family dynamics, concluding with a positive health update from Teddi's oncologist and reflections on aging gracefully in the fashion world.

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

Join our host, senior style icon and former mental health professional Theodora Krochman, and entrepreneur and documentarian Melissa Pierce as they interview Chicago's best and brightest and ask hard-hitting questions about fashion and culture.

In Episode 8, Teddi and Melissa welcome the multifaceted Arabel, a tech CEO with a juris doctorate who has made remarkable contributions to the technology and fashion worlds. As President and CEO of AAR Tech, founder of the nonprofit Pivoting in Heels, creator of the global Runway Latinx fashion event, and host of the Chic Innovator podcast, Arabel brings a unique perspective on how seemingly disparate fields can intersect to create powerful platforms for women's empowerment.

The conversation explores Arabel's fascinating journey from tech executive to fashion community leader, revealing how her analytical background and business acumen have shaped her approach to creating inclusive spaces in the fashion world. Through Runway Latinx, she has built a globally recognized platform celebrating Latin culture through fashion, gastronomy, mixology, and entertainment. The discussion delves into how her nonprofit, Pivoting in Heels, works to empower women professionally and how her podcast Chic Innovator continues this mission through a new medium.

As the conversation unfolds, they examine broader cultural questions about casual dressing trends, fashion as a tool for empowerment, and personal style evolution across different eras. Arabel's insights provide a refreshing perspective on how women can leverage fashion not merely as self-expression but as a strategic element in professional success and community building.

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

Follow Arabel on Instagram: @arabel22, @runwaylatinx, and @thechicinnovator

Join our host senior style icon and former mental health professional Theodora Krochman, and entrepreneur and documentarian Melissa Pierce as they explore the evolving role of women's fashion in the professional sphere. In Episode 6, Teddi and Melissa examine the seismic shift in workplace fashion from the era of "power suits" designed to help women blend in with their male colleagues to today's celebration of distinctly feminine professional style. They dive into how this transformation reflects broader changes in society as women increasingly outpace men in educational achievement and professional advancement. The conversation explores how the freedom to dress authentically in the workplace parallels women's growing confidence in owning their power and visibility. The discussion takes an intriguing turn as they connect the dots between reality TV's portrayal of wealthy women, the myth of the "down on their luck millionaire," and how these narratives influence public perception of successful women. They examine the political implications of these cultural shifts, including a frank discussion of Trump voters and gender dynamics in contemporary America. Through their signature blend of cultural analysis and personal experience, Teddi and Melissa make a passionate case for women stepping out of the background and into the spotlight – both in their professional presence and personal style.