Building Inclusive Fashion: Die With Your Boots On’s Bold Journey – Creativity Connects Ep.5

About the Podcast

Creativity Connects with Mikki Wilson is a Creative Collective podcast that goes beyond the brand and into the authentic journeys of women entrepreneurs who are members of the Creative Collective. Each episode, host Mikki Wilson sits down with a woman business owner from the Creative Collective community to explore her unique path, what drives her, and where she’s headed next. This series illuminates the moments, motivations, and messy middles that shape women’s experiences as creators and business leaders in the creative economy. Sponsored by Jenni Stuart Fine Jewelry

From Corporate Constraints to Creative Freedom: The Die With Your Boots On Story

Few stories capture the essence of authentic, inclusive fashion entrepreneurship like Amber Newberry and Lori Moran’s journey with Die With Your Boots On. From corporate disillusionment to building Salem’s boldest gothic boutique, their path demonstrates how personal necessity and friendship can evolve into powerful community impact.

In our latest Creativity Connects conversation, host Mikki Wilson explored the authentic story behind this dynamic duo’s business partnership. Their friendship spans years, providing a unique window into how two women transformed corporate frustration into a thriving inclusive fashion destination.

The Creative Soul Behind Authentic Expression

Amber describes her journey into inclusive fashion entrepreneurship as born from a profound realization about life’s brevity. “I just turned 40 the other day and I still don’t 100% know who I am,” she shares candidly, “but I think that what we do at Die with Your Boots On is very much about figuring yourself out and finding your expression.”

This authenticity-focused mindset shaped her approach after years in corporate environments where she “spent a lot of time in places where I was not able to express on the outside what I was on the inside.” Growing up in a “hyper religious family situation” and working in corporate jobs with “polo shirts and slacks and khakis,” Amber couldn’t show any personality. The loss of friends and family members during what she calls a “midlife crisis year” crystallized a simple truth: “Life is really short and I should maybe not devote all of my smarts to these companies and make millions of dollars for GameStop.”

Navigating Friendship to Business Partnership

Our community continues learning about successful collaborations between women entrepreneurs. Lori’s evolution from devoted friend to special projects manager highlights how authentic relationships can serve as the foundation for sustainable business partnerships. “I have been Amber’s friend since 2016,” Lori explains, “and when Amber first opened up the shop, every hour I wasn’t working at my full-time job I was helping them set up the store.”

This transition happened organically when Lori reached a breaking point in her corporate role. After fifteen years in a male-dominated industry, being passed over for a promotion became her catalyst. “I was kind of like, ‘Okay guys, are you big enough that you can hire me yet because I’m done with this place,'” she recalls. The job interview that changed everything? “This conversation happened over drinks in a kitty pool in my backyard during the pandemic.”

Rather than accepting limitations in traditional workplace settings, both women developed what Mikki identified as entrepreneurial thinking—recognizing their value and refusing to minimize their worth.

Building with Intentional Inclusivity

What drives someone to create a business that serves customers who have been systematically overlooked? For Amber and Lori, the answer centers on authentic representation and access. When Salem’s previous goth shop, The Fool’s Mansion, closed, Amber waited for someone else to fill the void. “I waited and I waited and then it was like three or four years later and no one still no one had opened up another goth clothing shop,” she reflects.

This commitment to inclusive fashion entrepreneurship extends far beyond token gestures. As Lori explains, “We don’t have a plus-size section—every section has plus sizes. The whole place has got plus-sized stuff in it.” This seemingly simple decision represents a fundamental shift in retail design, integrating inclusivity into every operational aspect rather than segregating larger sizes.

Their principled approach extends to vendor relationships. When suppliers promise extended sizes but fail to deliver, they risk losing those partnerships. “If you’re going to keep saying yes and then not doing it, then we’re done,” Lori states firmly, demonstrating how businesses can use purchasing power to drive industry change.

The Power of Community and Authentic Customer Experience

Perhaps the most compelling aspect of Die With Your Boots On’s impact centers on genuine community building through their business. Amber describes witnessing customers “entirely transform their wardrobe” and people “trying on dresses for the very first time in their life to experience wearing on the outside what they’ve always wanted to wear on the inside.”

These moments reveal the deeper purpose behind their work in inclusive fashion entrepreneurship. When a young customer saved birthday money to purchase a tote bag and said, “I just wanted to say thank you so much for having this store,” Amber realized they were “creating a better, weirder future for the youngins.”

The business has evolved beyond retail into a platform for drag shows, community events, and creative markets. Their previous experience with Daughters of Darkness, a “fem-led business creative dark business market,” provided essential community organizing skills that naturally transferred to Die With Your Boots On’s programming.

Scaling with Values Intact

As Die With Your Boots On has grown beyond Amber’s original vision of “a little boutique with me and maybe a part-time employee,” new challenges have emerged. The success has been both unexpected and rapid, leading Amber to acknowledge, “I don’t have a business degree or anything like that—I’m just going based on instinct and what I’ve learned.”

This honest admission reflects a reality many entrepreneurs face in inclusive fashion entrepreneurship and beyond. The skills required to create inclusive spaces, foster genuine relationships, and maintain principled vendor partnerships are often not covered in traditional business education. Their expansion to include The Ossuary demonstrates thoughtful growth that maintains core values while serving new customer needs.

Moving Forward Together

Amber and Lori’s story illuminates essential insights for our creative community: the power of authentic self-expression, the importance of principled business practices, and the long-term impact of creating genuinely inclusive spaces. Their journey from corporate constraint to creative freedom demonstrates how inclusive fashion entrepreneurship can evolve organically while staying rooted in genuine care for underserved communities.

As we continue to explore authentic entrepreneurial journeys, their experiences remind us that sustainable businesses often begin with personal necessity and grow through a persistent commitment to serving others. Whether you’re considering a career pivot, developing inclusive business practices, or seeking ways to create meaningful community impact, their approach offers valuable guidance: build with what you have, maintain your values, and never underestimate the power of authentic friendship in business.

What resonates most from Amber and Lori’s journey? How might you apply their inclusive fashion entrepreneurship insights and community-building approaches to your creative work? We’d love to continue this conversation and learn from your experiences with authentic business partnerships and inclusive community building.

Episode Description

In this dynamic conversation, host Mikki Wilson sits down with the powerhouse duo behind Salem’s boldest fashion destination. Amber Newberry, founder of Die With Your Boots On, and Lori Moran, special projects manager, share how their authentic friendship evolved into a business partnership that’s redefining inclusive retail. From escaping corporate constraints to building a gothic boutique that celebrates every body and style, they reveal the real work behind creating truly inclusive spaces.

Key Conversation Moments:

• How corporate limitations sparked entrepreneurial freedom
• The intentional decision to integrate plus sizes throughout the store
• Building community through drag shows, events, and authentic customer experiences
• Transitioning from friendship to business partnership
• Scaling challenges for businesses built on authenticity and inclusion

Connect with Die With Your Boots On:

• Store Location: 9 Church Street, Salem, Massachusetts
• Sister Store (The Ossuary): 77 Wharf Street, Salem
• Website: diewithyourbootson.com
• Social Media: Instagram and TikTok

Credits: Hosted by Mikki Wilson, founder of Dot Connector Consulting

Produced by Randyll Collum for Peabody TV (peabodytv.org)

A Creative Collective podcast (creativecollectivema.com)

Sponsored by Jenni Stuart Fine Jewelry