Transgender Makeup Services in NYC, Curated Just for You and Your Journey
Bespoke beauty and lifestyle services for trans women. Each session is thoughtfully tailored to support your journey, helping you confidently transition into the person you’re meant to be.
Step Into Your Next Chapter
Private Trans Female Makeup Services for Every Stage of Your Journey
Whether you’re beginning to explore your identity or fully embracing your transition, you’ll find guidance and support every step of the way. We're here to help you feel proud of who you are and who you’re becoming. With our skills and dedication, we'll hold your hand every step of the way.
Trans-Friendly Makeup, Beauty, and Lifestyle Services: Designed Around You
In NYC, sessions are available in-person, virtually, or as a blend of both. For clients outside the area, we offer personalized 2-3 day retreats tailored to your needs, creating space for self-discovery and support. Custom programs start at $6,000 per month with a three-month minimum, which includes your intake and online consultation. Retreats are tailored to complement your travel plans and lifestyle, providing a seamless and personalized experience.
→ Explore a Personalized Experience
Why Work With Jen Cayle Gaum?
For over 20 years as an international makeup artist, educator, and beauty expert, Jen’s approach to beauty goes far beyond traditional makeup application. Her philosophy has always been evident in her work with clients—instilling confidence and promoting self-love is at the heart of every transformation.
As an advocate for women, Jen is deeply committed to creating spaces where every individual feels celebrated and empowered. “Working with trans female clients is my true calling—these services matter profoundly, and safe, affirming environments can be hard to find. Supporting transfeminine clients allows me to extend my advocacy, ensuring that all women, regardless of their journey, enjoy the confidence and self-expression that beauty can inspire.
How It Works: From Makeup Lessons to Full Feminine Integration
To get started, simply complete a brief information form and submit the one-time $125 fee. After reviewing your details, we’ll connect by email to share next steps. If you’re ready to move ahead, you can book a private consultation for $575, where we’ll craft a personalized plan tailored to your needs.
Your Custom Plan Might Include:
Makeup, Beauty, & Skincare Coaching
Get personalized product recommendations and hands-on lessons designed for you.Styling, Shopping & Wardrobe Support
From accessories to breast forms, I’ll help you find what suits you—inside and out. Whether you prefer shopping together or having items sourced for you, the process is tailored to your comfort and style.Feminine Presentation & Guidance
We’ll cover voice, movement, posture, and walking in heels—skills for embodying your feminine identity. I’ll provide techniques and feedback to help you feel fabulous and authentic in your presentation.
Lifestyle & Gender Support
You’ll have a confidential, nonjudgmental space to process internal shifts and external concerns. As your coach and confidante, I’m here to help you talk through anything.Integration & Outings
Whether it’s lunch, a manicure, or a walk through the city as your feminine self, we can plan and experience these moments together.
The Investment
Custom programs start at $6,000/month (includes initial online consultation, 3-month minimum retainer)
Out-of-town clients can book a 2- or 3-day intensive/retreat, with the service clearly structured around your travel and lifestyle needs
A $125 fee applies to submit your initial contact form.
After the form submission, there is a $575 fee for an initial online consultation.
→ Let’s See If We're a Fit
What My Clients Say:
Working with Jen has been absolutely life-changing. As a trans woman, I struggled for years to feel comfortable in my own skin. Through her beauty and lifestyle coaching, I’ve not only learned how to highlight my features with confidence, but I’ve also discovered a deeper self-love I didn’t know was possible. For the first time, I feel fully seen, celebrated, and authentically myself." Robyn ★★★★★
What to Expect from Your Transgender Makeup and Confidence Coaching Experience
Clients receive focused, individual support. We create a plan matched to your specific goals, offering experiences like retreats, ongoing programs, or fully custom solutions. Sessions are virtual or in-person and always private.
→ Say Yes to Your True Self
Is This the Right Fit?
This is for those wanting to explore femininity through real, personal growth. The process is gradual, centered on confidence, not quick transformations or flashy makeup. If you seek honest, reflective guidance, you’ll benefit most. Join when ready!
Ready to Begin Your Feminine Transformation?
Personalized, private support is available in NYC or online. Limited spots ensure individual attention. If unsure, join the waitlist for updates on new openings.