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My Life in Heels

My Life in Heels

Written by: Tiffany Scott
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About this listen

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

© 2026 My Life in Heels
Social Sciences
Episodes
  • Episode 23 Dating, Desire, and Dysphoria | My Life in Heels
    Jan 19 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 episode is a gentle but real conversation for trans women and crossdressers who are figuring it out as they go.
    This isn’t advice from a distance—it’s lived experience, reflection, and reassurance that you are not broken for wanting connection, safety, and love.
    ✨ In this episode:
    • Wanting to be desired without shame
    • The difference between fetish and real connection
    • How dysphoria can show up while dating or being intimate
    • Red flags, green flags, and trusting your gut
    • A listener reflection moment to check in with yourself
    If dating has ever made you feel like you needed to shrink, hide, or apologize for who you are—this episode is for you.
    👠 My Life in Heels is a podcast about trans womanhood, self-discovery, courage, and choosing yourself—one step at a time.

    #MyLifeInHeels
    #TransPodcast
    #TransVoices
    #TransStories
    #TransWoman
    #TransWomen
    #Crossdresser
    #GenderExpression
    #TransFeminine
    #DatingWhileTrans
    #TransDating
    #DesireAndDysphoria

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    8 mins
  • Episode 22 Autumn Brown Outfit Ideas 🍂 Faux Fur, Boots & Budget Styling | My Life in Heels
    Jan 6 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 to wear underneath. For me, fashion isn’t just about trends — it’s about self-acceptance, choice, and dressing from the inside out as a trans woman.
    ✨ In this video:
    – Autumn brown outfit ideas
    – Faux fur coat styling (elegant & casual)
    – Brown suede boots & accessories
    – Wool knit dress & short brown dress
    – Satin vs corduroy skirts
    – Budget-conscious fashion with intention
    – Dressing as a trans woman with confidence

    Almost everything came together within £100, with the coats being the one decision I couldn’t make — so I chose softness and bought both. This video is about allowing yourself options and building outfits that feel right for you.
    If you enjoy thoughtful fashion, autumn styling, and honest conversations around identity and self-expression, I’d love for you to like, comment, and subscribe 🤎
    Let me know in the comments which piece or outfit you loved most!

    #AutumnFashion
    #BrownOutfits
    #FauxFurCoat
    #BudgetFashion
    #TransWoman
    #TransFashion
    #AutumnOutfitIdeas
    #MyLifeInHeels
    #LayeringOutfits
    #FallFashion

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    8 mins
  • Episode 21Winter Fashion in Heels: Style Tips to Stay Warm Without Losing Your Look
    Nov 29 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 look
    ✨ Winter-friendly fabrics that elevate your style
    ✨ Confidence tips to stay authentic and empowered
    ✨ My go-to heel picks for snow, ice, and everyday winter wear

    If you're looking for winter fashion inspiration, heel styling ideas, or just a boost of confidence to own your style—even in freezing temperatures—this episode is for you.

    📌 Don’t forget to like, comment, and subscribe for more episodes of My Life in Heels!

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    12 mins
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