Tiffany Scott

My Life in Heels

Society EN ↓ 28 episodes

Hosted by Tiffany Scott, this weekly podcast offers real, unfiltered conversations from within the Transgirl community. Join Tiffany and her guests as they share personal stories, insights, and experiences on topics ranging from gender identity and transition journeys to crossdressing, relationships, and beyond. Whether you're part of the LGBTQ+ community or an ally seeking understanding, this podcast is your space to listen, learn, and connect. #LGBT #Transgender #MTF #Crossdressing #Trans

Author

Tiffany Scott

Category

Society

Podcast website

www.buzzsprout.com

Latest episode

May 5, 2026

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Episodes

Episode 28 Protecting Your Peace | Boundaries, Femininity & Knowing Who Deserves Access to You 05.05.2026

In this episode of My Life in Heels, I’m talking about something that becomes incredibly important once you start feeling more like yourself — protecting your peace. As we grow in confidence, femininity, and self-acceptance, we start to realise that not everyone deserves access to us. Not everyone deserves our softness. Not everyone deserves our emotional labour. And not everyone who wants us… act...

Episode 27: Becoming Her: The Moment You Start Feeling Like Yourself 16.04.2026

• In this episode of My Life in Heels, I talk about something that comes after the doubt — the moment you slowly start feeling like yourself. • After dealing with imposter syndrome, overthinking, and questioning whether you’re “feminine enough,” there comes a shift. It’s quiet, gradual, and often unexpected… but it changes everything. • This episode is about that transition from trying… to simply...

Episode 26 Am I Feminine Enough? | Imposter Syndrome as a Trans Woman 31.03.2026

In this episode of My Life in Heels, I open up about something many of us experience but rarely talk about — feeling like we’re “not feminine enough.” Whether you’re a trans woman, crossdresser, or someone exploring your identity, imposter syndrome can show up in unexpected ways. Comparing yourself to others, feeling like you don’t quite belong, or questioning if you’re “doing it right” can be a d...

Episode 25 Fashion on a Budget: Looking Good While Becoming Yourself 17.03.2026

In this episode of My Life in Heels, we’re talking about something nobody prepares us for — how expensive becoming yourself can be. Building a wardrobe, learning your style, experimenting with presentation, and finding confidence in your identity often comes with financial trial and error. Many of us have closets full of outfits we loved when we bought them… but never actually wore. Today, I share...

Episode 24 Being Desired vs Being Respected | My Life in Heels 03.02.2026

In this episode of My Life in Heels, I explore the difference between being desired and being respected, and why learning to tell the difference was a turning point in my life. As a trans woman, attention and attraction often came before safety, stability, or self-worth. In this honest and reflective conversation, I talk about how desire can feel validating — especially early on — and how over tim...

Episode 23 Dating, Desire, and Dysphoria | My Life in Heels 19.01.2026

Dating as a trans woman—or even allowing yourself to be desired—can feel complicated, vulnerable, and deeply emotional. In this episode of My Life in Heels, I talk honestly about dating, desire, and dysphoria—how they show up in our bodies, our hearts, and our relationships. From wanting to be wanted, to navigating fetishization, to setting boundaries when dysphoria appears during intimacy, this e...

Episode 22 Autumn Brown Outfit Ideas 🍂 Faux Fur, Boots & Budget Styling | My Life in Heels 06.01.2026

Autumn is the perfect season for texture, layering, and warmth — and in this video on My Life in Heels, I’m sharing how I built an autumn outfit edit around brown tones, faux fur, and intentional styling, all on a near £100 budget 🍂 I walk you through each piece, from brown faux fur coats (yes, I bought two!) to suede boots, a matching handbag, dresses, skirts, and even the brown lingerie I chose...

Episode 21Winter Fashion in Heels: Style Tips to Stay Warm Without Losing Your Look 29.11.2025

Welcome back to My Life in Heels ! In this episode, we dive into winter heel-wearing hacks , cold-weather styling tips , and how to stay warm, confident, and authentically YOU during the chilliest months of the year. Whether you love stiletto boots, block heels, or your favorite high-heel staples, this guide will help you master:    ✨ Layering techniques that keep you warm without killing your lo...

Episode 20 “High Heels, High Tech: Making My First Album with AI | My Life in Heels Podcast” 13.11.2025

In this week’s episode of My Life in Heels, I open up about one of the most exciting and emotional projects I’ve ever created — my first full album, made with the help of AI. 💋🎸 I talk about how I used ChatGPT to co-write the lyrics, and Suno to bring the songs to life with music and vocals. From blues and country rock roots to personal storytelling and empowerment, this project has been a journ...

Episode19 “Real or Rendered — Finding Yourself in the Age of AI” 04.11.2025

My Life in Heels | Episode: “Real or Rendered — Finding Yourself in the Age of AI” Hey beautiful souls 💋 — I’m Tiffany Scott, and welcome back to My Life in Heels! In this episode, I’m diving deep into something that’s been on my heart: what it means to be real in a world shaped by artificial intelligence. From AI filters and “perfect” digital selves to songs written by computers, technology is c...

Episode 18 ✨ Finding Your Femme Energy | Embracing Confidence, Softness & Strength | 27.10.2025

In Episode 18 of My Life in Heels, I explore what it really means to find your femme energy — that radiant, intuitive, nurturing power that lives within us all. 🌸 This episode is about so much more than lipstick or heels. It’s about confidence, connection, and learning to embody femininity in your own unique way — whether you’re a trans woman, crossdresser, or simply someone reconnecting with you...

Episode 17. My 5 Top Tips to Express Your Inner You | Confidence for Trans Women & Crossdressers 09.10.2025

✨ Welcome, beautiful souls! ✨ In this video/podcast, I’m sharing my 5 top tips to express your inner you — designed especially for trans women and crossdressers who are exploring and celebrating their feminine side. 💖 This isn’t about “passing” or fitting anyone’s expectations — it’s about confidence, self-love, and feeling like the most authentic version of yourself. 💋 In this episode, we’ll...

Episode 16 ✨ Confidence on the Northumberland Coast | Trans Woman Bikini Beach Vlog 🌊 |titled Episode 30.09.2025

Join me on a beautiful trip to the stunning Northumberland coast as I enjoy a relaxing day at the beach in my bikini. 🏖️ As a blonde trans woman, this video is about embracing confidence, body positivity, and living authentically in every moment. On My Life in Heels, I share my personal journey, lifestyle vlogs, and experiences as a transgender woman navigating life with style, courage, and confid...

Episode 15, 15 Lessons from 15 Heels 25.09.2025

In this milestone episode of My Life in Heels, I’m sharing 15 lessons I’ve learned along my journey as a blonde in heels — from courage and confidence, to fashion hacks, to navigating love and visibility. Every heel step has taught me something, and today I’m spilling it all. 👠 What’s YOUR biggest lesson from your own journey? Share in the comments! ✨ Don’t forget to like, subscribe, and join me...

Episode14 “Looking Fabulous Without Breaking the Bank | My Life in Heels” 16.09.2025

✨ Welcome back to My Life in Heels! Today I’m sharing my best fashion on a budget tips — because looking fabulous doesn’t have to cost a fortune. As a trans woman, I know how tricky sizing and style can be, especially when money is tight. In this episode, I’ll share: My personal budget fashion journey 👠 Thrift store and online shopping hacks 🛍️ How to find affordable heels in larger sizes 👢 Cre...

Episode 13: The Soundtrack of My Heels-Music, Identity & Reinvention 09.09.2025

I reposted last weeks podcast again in error, the new one is now live x In Episode 13 of My Life in Heels, I share the songs that shaped my journey as a trans woman — from Lou Reed’s Walk on the Wild Side to Shania Twain’s Man! I Feel Like a Woman. Discover how music inspires confidence, resilience, and reinvention through icons like Cher, Whitney Houston, Madonna, Kylie Minogue, Miley Cyrus, and...

Episode 12 Tales from the Closet 👠 | Trans Fashion Wins & Fails (Crossdressing Stories) 02.09.2025

Every trans girl, crossdresser — honestly, every woman — has fashion wins and fails. In this episode, I’m spilling my own Tales from the Closet: ✨ The must-have nude stilettos every girl should own ✨ The time I actually wore a bin liner (yes… really!) ✨ My not-so-successful experiments with trousers & dungarees ✨ The fantasy of the “secretarial look” ✨ And my love-hate relationship with b...

Episode 11 🌟 Living Authentically: Interview with Charlotte Sometime | My Life in Heels 26.08.2025

In this episode of My Life in Heels , I sit down with the amazing Charlotte Sometime , a crossdresser and popular YouTuber with over 48,000 subscribers , to talk about self-expression, confidence, fashion, and finding community online. Charlotte opens up about her personal journey, her passion for crossdressing, and how her channel has inspired thousands of people to embrace their authentic selves...

Episode10 “10 Things I Love About Being a Trans Woman | My Life in Heels Podcast” 18.08.2025

In this milestone 10th episode of My Life in Heels, I celebrate the joy, beauty, and empowerment of living authentically as a trans woman. From the thrill of heels and fashion, to the intimacy of sisterhood, community, and pure self-love — I’m counting down ten things that make this lifestyle unforgettable. Join me as I share personal reflections on heels, hosiery, lingerie, makeup, jewellery, the...

Episode 9 "My Life in Heels: Clair Hughes on Transition, Triumph, and Living Authentically" 11.08.2025

#TransWomen #LGBTQ #GenderIdentity Join us on My Life in Heels as we sit down with trans woman Clair Hughes for an honest, heartfelt, and inspiring conversation about her journey of self-discovery, gender transition, and living life authentically. In this episode, Clair opens up about: Her personal story before, during, and after transitioning The challenges and triumphs of navigating gender ident...

Episode 8"Icons in Heels 👠 | Celebrating Trans & Crossdresser Style, Confidence & Power | My Life in Heels" 06.08.2025

✨ Icons in Heels 👠 | Hollywood Glam & Trans Trailblazers | My Life in Heels In this powerful and glamorous episode of My Life in Heels, we’re celebrating the Icons in Heels — from legendary Hollywood stars to inspiring trans and crossdressing personalities who have broken boundaries, owned their truth, and rocked heels with pride and power. 👠 We take a fabulous walk through history and pop...

Podcast Episode 7 “Dressing for Confidence, Not Approval | Crossdressing & Self-Love Tips” 27.07.2025

🎙️ Dressing for Confidence, Not Approval | My Life in Heels Podcast 👠 Welcome back to My Life in Heels—the podcast where gender expression, crossdressing, and self-discovery take centre stage. I’m your host, Tiffany Scott, and today we’re diving deep into a conversation every crossdresser, trans person, and gender-expansive soul needs to hear: how to dress for confidence, not approval. ✨ In this...

Episode 6 Queens of Evolution: Courtney Act, Alyssa Edwards, Miss Fame & RuPaul 21.07.2025

📺 Queens of Evolution: Courtney Act, Alyssa Edwards, Miss Fame & RuPaul  ✨ In this episode of My Life in Heels, we dive deep into the world of drag and celebrate four legendary drag queens who helped transform the art form as we know it: Courtney Act, Alyssa Edwards, Miss Fame, and the one and only RuPaul. 👠 From Courtney’s gender-defying advocacy to Alyssa’s high-energy dance legacy, from...

Episode 5 Crossdressing in the digital age 15.07.2025

In today's hyper-connected world, crossdressing is more visible and celebrated than ever before. From TikTok to Instagram, and online communities like Reddit and Tumblr, digital platforms have empowered people to explore and express gender fluidity, fashion freedom, and self-identity in bold new ways. 💻✨ In this video, we dive into: 👗 The evolution of crossdressing in online spaces 🌐 How...

Episode 4 Makeup and the crossdressing lifestyle. 07.07.2025

✨ Makeup and the Crossdressing Lifestyle | Tips, Talk & Transformation ✨ In this episode, we dive deep into the role makeup plays in the crossdressing lifestyle — from expression and identity to confidence and creativity. Whether you're just beginning your journey or you're a seasoned pro, this space is all about embracing who you are and having fun with your look! 🎨 What we cover...

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