Paint with Me: Digital Portrait Paintin…: is this $79 stack worth it for Drawing & Painting?
You know that specific frustration of staring at a blank canvas in Procreate, knowing you want to paint a portrait but freezing up because you don’t know where to start? You’ve got the reference photo, you’ve got the Apple Pencil, but the moment you lay down the first stroke, it looks flat, messy, or completely wrong. That gap between “I can draw” and “I can paint” is where most digital artists get stuck, especially when it comes to faces. (Paint with Me: Digital)
Paint with Me: Digital Portrait Painting in Procreate by Artwork by Gabrielle is built specifically to close that gap. Instead of giving you a vague theory lecture, it’s a real-time, step-by-step demonstration where you follow along as Gabrielle Brickey paints a portrait from scratch. It’s not just about watching someone else paint; it’s about understanding why she makes each move, how she simplifies complex features into manageable shapes of value, and exactly which brushes to use to get that painterly finish without getting lost in pixel-peeping details.
At $79, you’re getting a complete ecosystem for this specific project: over four hours of video instruction, the exact Procreate brushset she uses, high-quality reference files, and paper textures. If you’ve been trying to break out of the “sketchy” phase and move into confident, finished digital portraits, this is the kind of structured, hands-on guidance that actually changes your workflow. (Paint with Me: Digital)
Quick answer
| Best for | Digital artists who want to learn portrait painting through a real-time, follow-along demonstration in Procreate. |
| Skip if | You are a complete beginner who hasn’t yet learned basic proportion and shape (the seller recommends their foundational guide first), or if you don’t have access to an iPad and Procreate. |
| Price | $79 (Code PORTRAITS available for 10% off) |
| Format | 4+ hours of video instruction, Procreate brushset, HQ reference files, and paper textures. |
| One-line take | A comprehensive, real-time painting class that demystifies the process of turning a reference photo into a finished digital portrait. |
What you’re actually buying
This isn’t a collection of disconnected tips or a generic “how to use brushes” tutorial. It’s a complete portrait painting session, captured in real time. When you buy Paint with Me: Digital Portrait Painting in Procreate, you’re stepping into a virtual studio with Gabrielle Brickey, an artist with over 20 years of experience in portrait drawing and painting. The core of the offer is the 4+ hours of video instruction, where you watch her make every decision from the initial layout to the final details. This is crucial because portrait painting is rarely about isolated steps; it’s about a continuous flow of judgment calls that you need to see in context to truly understand.
The value here is heavily amplified by the included resources. You don’t just get the video; you get the Procreate brushset she uses throughout the lesson. This is a common pain point in digital art tutorials—watching an artist use a brush you don’t have and trying to replicate the effect with your own default tools. Here, you can download her exact brushes, so the texture, opacity, and blending behavior match what you’re seeing on screen. You also get HQ reference files (in Procreate, Photoshop, and raw JPG formats) and HQ paper textures, which means you can start with the exact same starting point she did, eliminating the friction of finding your own reference or setting up a canvas. (Paint with Me: Digital)
The curriculum focuses on the foundational skills that make portraits look professional. You’ll learn how to place your subject with confidence, how to paint using simple shapes of value (a technique that saves hours of frustration), and how to maintain accurate facial proportions. Perhaps most importantly, the course teaches you how to simplify your painting and avoid getting lost in the details—a common trap for digital artists who have the power to zoom in infinitely. By learning to work with broader shapes first, you’ll develop a more painterly, cohesive style rather than a muddy, overworked one. (Paint with Me: Digital)
One buyer highlights the longevity and quality of Gabrielle’s teaching, noting in Gumroad reviews: “All Gabrielle classes are amazing! I have been learning from her for many years now, and she is one of the best teachers there is.” This speaks to a teaching style that remains effective and valuable over time, not just a one-off trick.
Why it’s on our radar
This course stands out because it solves a very specific, high-friction problem: the transition from line art to finished painting in a digital environment. Many tutorials focus on either drawing or painting, or they provide theory without the hands-on demonstration. Paint with Me: Digital Portrait Painting in Procreate bridges that gap by offering a real-time, step-by-step demonstration that shows the actual process, including the mistakes and adjustments that happen along the way.
The inclusion of the exact brushset and reference files is a significant differentiator. It removes the “tool gap” that often prevents learners from replicating a tutorial’s results. You’re not just watching; you’re equipped with the same tools to practice alongside the instructor. This makes the $79 price point compelling for anyone serious about improving their digital portrait skills, as it provides a complete, self-contained learning environment for this specific project. (Paint with Me: Digital)
Another buyer captures the quality of the instruction in Gumroad reviews: “One of the best digital painting tutorials I’ve ever seen.” This suggests that the course delivers on its promise of high-quality, practical instruction that stands out in a crowded market of digital art tutorials.
What actually matters
Before you check out, consider these specific aspects of the course to ensure it fits your current skill level and setup: (Paint with Me: Digital)
- Prerequisites: The seller explicitly notes that if you are completely new to portrait painting, you might want to check out their foundational guide, Drawing and Painting Portraits: A Guide for Artists, first. This course is designed for those who have a basic understanding of drawing and want to move into painting. If you struggle with basic proportions or shapes, this might be a step too far. (Paint with Me: Digital)
- Software and Hardware: You need the Procreate app, an iPad or iPad Pro, and an Apple Pencil. While the seller mentions that all mediums are welcome and you can follow along with traditional tools, the included brushset and files are optimized for Procreate. If you use a different digital platform (like Photoshop on a desktop or Krita), you can still learn from the video, but you won’t be able to use the provided brushset directly. (Paint with Me: Digital)
- Real-Time Format: The course is a real-time demonstration. This means you’ll be watching a continuous painting process, not a series of short, isolated clips. This is great for learning the flow and decision-making process, but it requires a longer time commitment to watch and follow along. Make sure you have the bandwidth for 4+ hours of focused practice. (Paint with Me: Digital)
- Style Focus: The course focuses on creating painterly portraits. If you’re looking for a hyper-realistic, photo-digital style, this might not be the right fit. The techniques taught here are geared toward simplifying forms and using value shapes to create a more artistic, painted look. (Paint with Me: Digital)
Mid-check
If you’re ready to dive into a real-time portrait painting session and want the exact tools to follow along, See current options.
FAQ
Do I need to be an advanced Procreate user to take this course? No, you don’t need to be an advanced user, but you should be comfortable with the basics of the app. The course focuses on painting techniques and portrait-specific skills, not on teaching you how to navigate Procreate’s interface. If you’re new to Procreate, you might want to spend some time familiarizing yourself with the app’s basic tools before starting. (Paint with Me: Digital)
Can I use this course if I paint traditionally? Yes, the seller encourages all mediums. While the included brushset and files are for Procreate, the techniques taught—such as using shapes of value, simplifying details, and understanding proportions—are universal. You can follow along with traditional paints, pencils, or other digital tools. (Paint with Me: Digital)
Is this course suitable for complete beginners to art? The seller recommends that complete beginners to portrait painting consider their foundational guide first. This course is best for those who have some drawing experience and want to learn how to paint portraits digitally. If you’re brand new to art, you might find the pace and techniques a bit overwhelming without the foundational skills. (Paint with Me: Digital)
What formats are the reference files provided in? You’ll get high-quality reference files in Procreate, Photoshop, and raw JPG formats. This flexibility allows you to use the reference in whatever software you prefer, even if you’re not using Procreate for the actual painting. (Paint with Me: Digital)
Bottom line
If you’re stuck in the “sketchy” phase and want to learn how to create confident, painterly portraits in Procreate, Paint with Me: Digital Portrait Painting in Procreate is a strong choice. It offers a complete, real-time learning experience with the exact tools you need to follow along. The $79 price is a fair investment for 4+ hours of expert instruction, a custom brushset, and high-quality reference materials. If you’re ready to move beyond basic line art and into the world of digital painting, this course provides the structure and guidance you need to make that leap.