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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
Overwhelmed by packing for a business trip with limited suitcase space and little time to plan outfits
Worrying that your outfits are a bit "blah" when you know you could be admired for your unique style tastes
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
Struggling with a wardrobe that doesn't quite match your professional goals or personal style
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 best features and make you feel like the leader you are
Have a wardrobe that perfectly aligns with your professional aspirations 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 fresh, stylish, and ready to take on the world with curated and professional looks
Achieve your style goals and maintain a strong, confident professional presence that evolves 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 defining a personal brand that truly captures your one-of-a-kind identity and leadership style.
You'll become a pro at choosing the colors, cuts, and designs that make you look and feel like the leader you are. No more second-guessing, just dressing with purpose and total confidence.
Introducing the Style Mastery Course
Designed Specifically for Leaders & Executives Like You
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We'll fine-tune your new and improved wardrobe, making sure you know exactly how to care for your clothes, and wrap things up by answering any lingering questions.
Module 4: The Final Steps
In this module, you'll learn how to create a wardrobe budget that works for you, discover some amazing sustainable brands, get a crash course in accessorizing, and pick up some grooming tips.
Module 3: The Finishes
It's time to give your closet a total makeover! We'll edit your wardrobe, get everything organized, figure out your ideal level of dress, and put together a capsule collection that will make getting dressed a total breeze.
Module 2: The Frame
We'll kick things off with a deep dive assessment, set some goals, uncover your perfect colors, and get to know your unique body type to help you start developing that executive presence.
Module 1: The Foundation
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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.
Get your hands on my coveted collection of insider style guides and resources. These resources are packed with everything you need to take your style to the next level, from mastering the art of accessorizing to becoming a pro at picking the perfect outfit.
All-Access Pass to My Secret Style Vault:
I'm here for you, every step of the way. With ongoing support via email during office hours, you can send me a note whenever you need a little style advice or encouragement to keep you moving forward and feeling fabulous.
30 Days of Style SOS Support:
Each phase of the course comes with a dedicated 45-minute Zoom call with yours truly. These aren't just quick check-ins—they're deep dive style strategy sessions where we'll customize everything to fit your unique needs and goals.
One-on-One Zoom Sessions:
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 perfecting my craft and seeing firsthand the incredible impact that personal style can have on your confidence and career. And now, I'm thrilled to share all of that expertise with you.
This isn't your average style course. We're diving deep into what makes a leader look and feel like a powerhouse—polished, put-together, and ready to take on anything.
What makes this program so special is that it's not just about educating you—it's about empowering you. You're not just going to learn about clothes; you're going to discover how to align your outer style with your inner ambition, creating a personal brand that screams authenticity and authority.
I'm personally inviting you to join me on this adventure.
Together, we'll unlock the full potential of your wardrobe and create a look that's as unique as your fingerprint and as powerful as your vision.
I can't wait to meet you on the other side of style,
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 the cuts, colors, and styles that fit your body and make your natural skills shine even brighter
The unshakeable confidence that comes with having a perfectly curated professional wardrobe that shows the world exactly who you are
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 walking out the door every single day knowing you look like a million bucks—because when you feel good, you do good
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 career goals is a key focus of this course. We'll work through targeted exercises and have plenty of in-depth conversations to help you set "micro-intentions" that seamlessly blend what you love with the message you want to send through your style.
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 type. You'll walk away with the knowledge you need to choose pieces that fit and make you look and feel amazing.
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!
