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Ready to turn your wardrobe into a powerhouse of confidence?
Style Mastery Course for Leaders & Executives
Letting amazing pieces gather dust in your closet because you're not sure how to wear them
Packing for trips feels overwhelming because you are unsure how to create stylish, versatile outfits with limited space and time.
Feeling like your outfits are a bit “blah” when you know there’s clever style tips out there, but unsure which one’s work for you.
Setting big style goals, only to find yourself falling back into the same old-fashioned ruts
Feeling lost when it comes to figuring out which styles make you look and feel your best
Your wardrobe feels out of sync with who you are today, no longer reflecting your personal style, values, ideas, or creativity.
Wasting precious time every morning trying to put together the perfect outfit for your day
Getting frustrated when your clothes don't play nice together, leaving you with limited options
Does this sound like you?
Confidently choose styles that highlight your natural beauty and reflect your authentic self
Build a wardrobe that aligns with your lifestyle, goals, values, and personal style
Streamline your morning routine with a clear plan for what to wear, making getting dressed simple and easy
Feel inspired by your wardrobe, mixing and matching like a pro to create cohesive outfits
Make the most of every single piece in your closet, knowing exactly how to style them for any occasion
Step out the door feeling put-together, comfortable, and fully yourself — ready for anything
Reach your style goals and maintain a confident, effortless presence that grows with you
Now, Imagine If You Could...
— Alessia F., Risk & Sustainability Officer —
Her ability to adapt style and color to one’s personal and professional pursuits is the ultimate confidence booster.
jenny’s work is a rare find!
Here's what you'll discover inside:
This holistic style course is about so much more than your wardrobe - it’s about trusting your intuitive knowing, embracing your one-of-a-kind personality and learning which styles bring out your natural beauty, confidence, and joy.
You'll become a pro at choosing the colors, cuts, and designs that make you look and feel good about yourself. No more second-guessing, just dressing with intention and total confidence.
Introducing the Style Mastery Course
Designed Specifically for Leaders, Go-Getters, and Entrepreneurs Like You
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Understand what works for your shape, your life, and your personality. Learn to choose fabrics, silhouettes, and levels of formality that feel authentic and elevated.
Module Four: Fit, Fabric, and Function
Uncover the power of color in this playful, eye-opening module. You'll identify the shades that flatter you most and build a palette that enhances your natural beauty.
Module Three: Hue are You
Discover what personal style really means for you. Learn how to tap into your inner wisdom and create a wardrobe that reflects your lifestyle, energy, and goals.
Module Two: Defining Personal Style
Start by uncovering your story, values, and what lights you up. This foundation guides your style journey, aligning your wardrobe with the life you want to lead.
Module One: Vision & Mindset
Before you buy a single thing, we’ll edit and reimagine what you already have. Create clarity and confidence through intentional organization and fresh new pairings.
Module Six: Shop Your Closet First
Explore the overlooked details that change everything—from the right undergarments to grooming habits and simple care tips that extend your wardrobe’s life.
Module Five: Alterations and Undergarments
Understand what works for your shape, your life, and your personality. Learn to choose fabrics, silhouettes, and levels of formality that feel authentic and elevated.
Module Four: Fit, Fabric, and Function
Uncover the power of color in this playful, eye-opening module. You'll identify the shades that flatter you most and build a palette that enhances your natural beauty.
Module Three: Hue are You
Before you buy a single thing, we’ll edit and reimagine what you already have. Create clarity and confidence through intentional organization and fresh new pairings.
Explore the overlooked details that change everything—from the right undergarments to grooming habits and simple care tips that extend your wardrobe’s life.
Module Five: Alterations and Undergarments
Learn to shop with purpose and joy. Discover brands, plan budgets, and use custom shopping tools to build a wardrobe that feels fresh, fun, and truly yours.
Module Seven: Finding the Perfect Pieces
Module Eight: Creating Your Perfect Looks
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These bonuses aren't just a little something extra—they're mini services that will take your style transformation from ordinary to extraordinary.
Your bonus Soulful Style Guide brings it all together—color, chakras, and accessories—in one beautiful, intuitive resource. Learn how to align your energy and expression for a style that feels deeply you, inside and out.
Soulful Style
Guide
Your bonus Sustainable Shopping List is filled with curated brands, timeless staples, and smart tips to help you shop with intention—so you can build a wardrobe that aligns with your values and your style. Thoughtful, not wasteful.
Smart & Sustainable Shopping List
At the end of the course, you’ll get a private 45-minute Zoom session with yours truly—a personalized style strategy call to answer any lingering questions and ensure everything is customized to your unique needs, lifestyle, and goals.
One-on-One Zoom Session:
When you embark on this style journey, you're not just getting the step-by-step course modules. You'll also receive these exclusive bonuses to take your learning to the next level:
Plus, You'll Get These Exclusive Bonuses
— John D., Consultant —
"The process was easy and informative. People started to comment on my ‘look’ almost every day. My confidence in how I dressed and styled outfits soared."
"Jenny made it very easy to mix-n-match without error.""
I’ve spent years honing my craft and witnessing firsthand how personal style can transform not just how you look, but how you feel and how you show up in every part of life. And now, I’m excited to share that expertise with you.
This isn’t your average style course. We’re going far beyond trends or what’s “in.” This is about helping you show up as the most confident, authentic version of yourself — whether that’s at work, at brunch, on vacation, or simply running errands.
What makes this program truly special is that it’s not just about teaching you how to dress — it’s about empowering you to create a style that aligns with who you are and how you want to be seen. You’ll learn how to reflect your inner self through your wardrobe.
I’m personally inviting you to join me on this journey. Together, we’ll unlock the full potential of your closet and craft a wardrobe that feels as unique as your fingerprint and as powerful as your presence.
I can’t wait to meet you on the other side of this transformation. I’m here to be your guide, your coach, and your biggest cheerleader as you step into a style that truly feels like you.
I'm here to be your guide and champion on this journey to revolutionize your style and how you show up in the world.
Hey there, I'm Jenny Bailey.
Coming soon
The relief of having a clear, custom plan that perfectly aligns with your style goals and busy lifestyle
The absolute joy of discovering how amazing you will feel when you let your natural beauty, personality, values, and ideas influence your style aesthetic
The confidence of a curated wardrobe that reflects your brilliance and lets your ideas speak before you do.
The thrill of becoming a style master and seeing your executive presence and day-to-day interactions get a level-up in the process
The satisfaction of stepping out each day aligned inside and out—because when you feel good, you do good.
No more guessing how to describe your style—this course gives you the words and visuals to express it with ease.
But, when you decide to team up with me in this course, you’ll enjoy:
Wasting hours and hours trying to crack the code on what styles and colors look best on you—time that could be spent doing anything else
Dealing with the frustration of putting together outfits that just don't quite hit the mark, leaving you feeling less than your best
Pouring your energy into a never-ending cycle of trial and error that leaves you drained and no closer to your goals
Feeling lost when it comes to matching your wardrobe to your professional goals and personal aesthetic
Running the risk of sticking with a closet that doesn't do your leadership skills and personal brand justice
When you decide to tackle your style transformation on your own, you might face:
Let’s Weigh Your Options.
Should You Go At It Alone, Or Team Up With Me?
— Cynthia R., Professional Musician —
Jenny was the alchemist that combined the elements of who I am and what I wear in a way that helped me shine as my authentic self.
And that’s really what Jenny is about – using style as a way to help people shine.
She calibrates her deep knowledge of fashion and style with her clients’ unique characteristics and goals to produce a result that is far greater than the sum of its parts. I can’t recommend Jenny highly enough.
You will not be disappointed!
Got Questions? I've Got Answers!
frequently asked questions
Absolutely! Whether you're looking to make a few small tweaks to your current look or start completely from scratch, this course meets you exactly where you are. We'll kick things off by taking a deep dive into your style baseline and your goals so that every step of the process is customized to your unique needs.
Aligning your personal style with your lifestyle, goals, and how you want to show up in the world is a key focus of this course. Together, we’ll work through thoughtful exercises and meaningful reflections to help you set micro-intentions that blend what you love with the message you want your style to communicate.
I've designed this course to fit even the busiest of schedules. Expect to set aside about 2-3 hours per week to watch content and put what you learn into action. And remember, investing time in your style is investing in your confidence and professional presence!
Absolutely! One of the core focuses of the course is learning which cuts and design elements work best for your unique body silhouette. You'll walk away with the knowledge you need to choose pieces that fit and make you look and feel amazing.
What kind of support is included throughout the course? Do you want to keep that you will be available via email? We should talk about this
In addition to the course modules and our live Zoom sessions, you'll also get access to ongoing support from me via email during office hours. This means you can reach out whenever you have a quick question or need some advice as you put your new style skills into practice. And for those bigger, more complex style conundrums, our Zoom calls and final one-hour session are the perfect opportunity to go deeper.
If you send a message outside of these hours, please keep in mind that it may take me some time to respond. I strive to get back to you as quickly as possible, but to maintain a healthy work-life balance, I prioritize messages received during office hours. If your question is urgent, feel free to send a follow-up message during office hours, and I'll do my best to address it promptly.
A major part of the course is about giving your closet a complete edit and refresh. We'll go through your existing pieces and figure out how they can be mixed, matched, and updated to create a new look that aligns with your style goals. You'll learn how to create fresh, versatile outfits using what you already have, so you can get the most out of every single item.
I know that change can be intimidating, but that's exactly why I'm here—to guide you through the process one step at a time. This course provides the perfect balance of support, guidance, and encouragement to help you push past those comfort zone boundaries and embrace the style transformation of your dreams.
You better believe it! As part of the course, you'll get tons of recommendations that can take your style journey to a new level. These hand-picked resources are the perfect way to get inspired and have some fun as you explore new ways to express yourself through your personal style.
— Armanda B., Retired Librarian, U of C —
"I learned a lot more about colors that do and do not work for me, and my color archetype. I left with a color fan that I pull out all the time when shopping. I am still wearing those colors!"
"I highly recommend her color services."
Your style transformation starts the second you say yes to this course. Give yourself the gift of unshakeable style confidence—not just for today, but for the rest of your life.
Because this is about so much more than just the clothes you wear.
It's about stepping into your power, owning your unique brand of brilliance, and showing up as the most incredible version of YOU imaginable.
Radiate Confidence Tomorrow!
