Your strategic Style awaits
Understanding style as the outward breath of inner wisdom, I share the methods and mastery that will bring your truest self into full expression.
Your authentic wisdom deserves strategic styling.
Wardrobe Styling & Color Analysis
for leaders, visionaries, and entrepreneurs
Located in SF Bay Area and
San Diego County.
Travel Upon Request.
Discover my Story
I've always had an eye for good design. As I became more aware of architecture and fashion styles, my curiosity took over and I've made it my life's work to study color and design principles.
I'm passionate about sharing this sage advice with leaders and visionaries like you. Together, we'll blend your personal colors and design with your authentic presence, which will boost confidence in a poetic way.
Pearls of Wisdom from Decades of Work
wardrobe stylist & color analysis maven
Hey there, I'm Jenny Bailey.
— Christina S., Attorney —
My confidence soared and I won many more cases following our work together. She’s an expert with color and style, and an absolute pleasure to work with.
jenny’s style coaching changed my life!
just for you
Tailored Style Solutions
Enroll Now
Unlock the secrets of style, all at your own pace. Learn to curate outfits that not only flatter your figure but also make you feel fantastic. Get ready to walk into every room with head-turning confidence.
Style Mastery Course
smile for the camera
Imagine having an image expert who ensures your look is always on point, whether you're commanding a crowd or making meaningful connections. I'll handle the details, so you can focus on leaving a lasting impression.
Spotlight Styling
Discover your style journey
Ready for a style experience? Dive into a personalized journey where we'll fine-tune your presence to mirror your boldest dreams. Step into every role feeling empowered, authentic, and unstoppable.
The Confident Leader Style Blueprint Experience
Let’s Elevate Your Style
Showcase personality & draw focus
Accessories
Define presence & approachability
Cuts
Express comfort & sophistication
Fabrics
Set the tone & shape perceptions
Colors
I'm here to show you how intentionally selecting colors, cuts, fabrics, and accessories can transform your style into a communication superpower. Get ready to enhance how others see you and boost your performance in every professional interaction.
a wardrobe where every piece is a powerful statement about your strengths, creativity, and leadership.
Picture this:
Style knowledge creates lasting confidence.
— GINA D., BUSINESS COACH —
"In working with Jenny, I've learned about color, shape, and style. I have the confidence knowing which colors work best for my skin tone. And I never leave the house without my color palette!"
"I used to think looking good was a happy accident and now I know there is an art and science to it."
Head to the Blog
Read The Post
From Classic to Creative: 10 Special Occasion Looks for Women
Read The Post
The Capsule Wardrobe: Building a Timeless Professional Wardrobe
Read The Post
Dressing Up Denim: Getting Jeans Party-Ready
Shopping strategies, clothing care, workplace style ideas, sustainable brands, and hidden gems to visit are all packed and ready for you to read.
Expert insights and stories to elevate your professional presence and personal style.
— The Style Blog
Cachet
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Dive deep into your closet, lifestyle, and shopping habits. Grab my The Empowered Worksheet — it's FREE!
Plus, when you download, you'll get exclusive access to my newsletter packed with style breakthroughs and VIP offers.
Discover the gaps between your daily activities and your current wardrobe.
