or Why You Should Try This Exercise from David Kibbe’s New Book
I recently tried an exercise from David Kibbe’s new book, as explained by Milli on YouTube, and it was incredibly insightful. Let’s get into it:
The Exercise Breakdown
Step 1: Use Pinterest to search for images of six specific things:
Sky
Landscape
Building
Tree
Flower
Gown
These should spark some feeling inside of you.
Then, add two other images that spark emotions or feelings in you (these can be anything that resonates with you personally). I made a new secret board that contained these images.

Step 2: Once you have finished choosing your images, look at them again and make sure they really resonate. Then, I downloaded each image that was my final image for each category.
Step 3: Open canva and add a grid of frames to your board. I used the presentation size (16:9). Add your images to this board so you can see them all next to each other. Close your eyes and then open them to double check the board creates a feeling within you. I broke the rules and had 10 images instead of 8. Oops!

Step 4: Note what that feeling is! Then, reflect on what what words are coming up for you as you look at the board as a whole, and each image. One way to do this is if you had to just pick one word, what would it be (for each image)? I just wrote down words of what I was noticing on the board first.

How ChatGPT Helped Me Analyze the Images
Next, I used ChatGPT to help me make sense of the board as a whole. To get another “eye” on the images. This analysis gave me a clearer understanding of the feelings behind my choices and how they relate to my overall aesthetic preferences.
So for example I uploaded my dream board to chatgpt (using chatgpt 4.0) and asked it to interpret what three words it would pick to exemplify the images.

The words it came up with were: Ethereal, Contrasted, and Introspective.
I resonated with the words here although I usually don’t consider myself as dressing “ethereally” so that was an interesting take. I also had my list of which words I picked from the first part of the exercises.
Taking it a Step Further—Creating Outfits
I realized that I could ask ChatGPT to create some outfit formulas based on my board! It picked three outfits based on each word, but I realized what I really wanted was ONE outfit that was representative of all three words, so I told it so.

I personally don’t often wear dresses or structured blazers, and tend to dress in a more “tomboy” style, so I gave it this feedback and that I wanted ONE outfit formula, and it had this to say:
The Outfit Formula (Tomboy Edition)
- Relaxed, flowy top – A sheer or lightweight button-up (think organza or soft cotton gauze) in a muted or washed-out color, worn slightly oversized. Layer over a fitted tank or turtleneck for depth.
- Loose, slouchy pants – Wide-leg trousers or relaxed pleated pants in a structured fabric like wool or twill to create contrast against the floaty top. A deep charcoal, inky blue, or soft cream would work.
- Unexpected color pop – A single bold element, like red socks peeking out, a cobalt crossbody bag, or an electric pink cap/beanie.
- Footwear mix – Chunky boots (Docs or a similar platform style) or sleek sneakers (like Adidas Sambas or Common Projects) to balance ethereal and grounded energy.
- Conceptual accessory – A single sculptural ring, a book tucked under your arm, or wire-frame glasses (even if non-prescription) for that introspective, artistic touch.
- Layering piece – A draped, longline cardigan or an oversized, deconstructed bomber jacket instead of a structured blazer.
Stay tuned for next week as I try out some of the formulas suggested with my own clothes, and see if the AI ‘nailed’ it!
Why You Should Do This Exercise
Connect with Your Inner Style: The exercise helps you understand your emotional connection to certain shapes, colors, and elements.
Clarity for Personal Style: By identifying what resonates with you, you’ll gain clarity on what makes you feel aligned in your clothing choices.
Improve Fashion Decision-Making: This exercise can be a great starting point for narrowing down your wardrobe and style choices.
Quick Tips to Get Started:
Be intentional when choosing your images. Don’t overthink it—just pick what feels right.
Reflect on the connections between the images and your feelings.
Use the exercise to help define and refine your personal style and aesthetics.
Go in with no preconceived notions! Try to pick images just of what you like, not so they “fit” with your perceived personal style.
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This exercise was a powerful way to tune into what truly sparks joy and alignment in my personal style. Give it a try, and see how it can help you connect with your own fashion essence!
Buy David Kibbe’s New Book: Power of Style: A Guided Journey to Help You Discover Your Authentic Style
Watch Milli’s YouTube video.