Imagine your life with more confidence. More smile. More style.


Get ready to get up, dress up, show up and never give up even when it scares you. Over 7 weeks you’ll create space in your life to truly focus on being 100 percent yourself.

This one-of-a-kind experience provides a clear step-by-step approach to an authentic life and style. As you follow my 3 pillars of true transformation you’ll engage in a powerful process that will help you curate both your closet and your confidence. After this you’ll be able to move past the obstacles that get in your way as you internalize that your beauty comes from being a strong, stylish and self-confident woman. 

We’ll talk about how to connect with who you really are — inside and out — and what you really want. I’ll ask questions you know you need to answer but haven’t asked yourself yet. I’ll share my most important lessons, answer your questions and guide you through activities that you can implement right away. You will be thinking, dreaming and taking action to empower your life as you make that crucial shift to a woman living with a wondrous sense of self and style.


Get ready to feel a sense of joy and confidence that will have you growing in ways you never thought possible as you tap into the power of being yourself. I’m honoured to lead you through your transformation based on my best-selling book. Throughout the lessons I will take you on a step-by-step journey toward discovering your true self as we dive deeper into my beliefs and research. You will get the tools, techniques and keep-it-real solutions you need to make friends with yourself — and fashion, once and for all. What I’m offering you is what I’ve learned. I’ll share stories from my own struggles and the processes that help me journey toward the woman I know I am.



Are you ready to answer the most important questions of your life? If you are ready to eliminate the self-sabotage, fear and uncertainty, I’ll help you awaken your inner voice and say YES to yourself. You’ll get clear about what you can do on your life-long journey to learn, transform and expand your life experiences in pursuit of happiness – and that perfect outfit.


You don’t have to look perfect or have a perfect life to be happy and  this program will give you something you won’t find in stores: confidence. I’d be breaking a girlfriend code if we didn’t talk about clothes, so I’ll help you pick out something to wear for the special occasions (and the day-to-day moments) that stand for your life. I’ll be there for you, offering advice on how to wear your life with the confidence that epitomizes the amazing woman you are – no matter what your size, shape or age.


I’ll encourage you to embrace life with grace and gumption as you claim your beauty, feel your power and be inspired to celebrate your individuality. By getting back in touch with your essential self you will rediscover your dreams and restore your passion for life with the confidence you need to make the changes you long for in your life and your personal style.

uplifting…intimate…encouraging…motivating…a must-read for all women.

5 Stars
Readers Favorite


This is a book I know I will be coming back to again and again. It truly spoke to my heart. I sat down the book after finishing the last page, feeling so happy to be me, so excited for the future, and so grateful for the present.

5 Stars
MyStyleSpot — Amazon Top 50 Reviewer

Hello. If you don’t know me, I am Helene Oseen. As an ambassador for women I have realized a career and a calling around making women feel good about themselves on the inside, and empowering them to reflect that on the outside. As a veteran in the fashion and style industry I have been observing, advising and styling women for many years. Many call me their fashion therapist. I have seen first-hand the healing power of style and how it can help a woman say hello to the world with a little more confidence each day.

I am an author and a long-time Fashion 911® newspaper columnist and weekly television contributor. I have been speaking on stages for many years. As founder of the Ultimate Pajama Party ® I hosted women’s luxury retreats in resort locations across the country and internationally. I feel honoured to have been a recipient of the Global Television Woman of Vision Award being recognized as a woman who has implemented her passion and whose personal dedication and actions inspire others. You’ll also find me in television, radio and print interviews. Most important, I am a mom, grandma, wife, daughter and friend who is still young enough to enjoy fashion, old enough to have seen the trends before and friendly enough to keep it fun.

I’m not trying to impress you, but to impress upon you that I too am a woman who struggles with the feeling that I am not good enough. Often I feel like I don’t measure up. My life, just like yours is a work in progress. I opened myself up to a new way of living that helped me make my life more awesome, interesting and fun. Today, my life is perfectly imperfect.

To be honest, I’m just trying to figure it out as I go. My life. My outfits. Everything.



PS. Take yourself off the discount rack. There will always be someone who can’t see your beauty and your worth. Don’t let it be you.




Can you remember who you were before the world told you who to be? Do you recognize yourself when you look in the mirror? Truth is, when you enhance the outside it also sparks something on the inside. Being a stylish woman and living a beautiful life isn’t about looking chic 24/7 or being superficial. It’s about discovering yourself, owning your look and showing the world who you are in your own standout style

  • Reconnect with who you are and what lights you up on a regular basis and re-engage with your essence.
  • Identify small changes that can make a big difference on your path to your most authentic self and style.
  • Understand the soul of your style and define the dimensions of your fashion personality.


Sometimes life doesn’t go according to plan. Other times you start to feel a restlessness and are ready to shake up the status quo. Whether you are facing small disappointments or heartbreaking tragedies, unwanted change can blindside you.  Even change you choose can throw you for a loop as you shake things up for the better.

  • Embrace 7 empowering ways to successfully adapt to change (whether it’s welcome or not).
  • Be specific about the areas in your life where you will create change this year and learn to navigate the inevitable ups and downs.
  • Do some soul-searching in your closet as you get your clothes under control and let go of the things that no longer work for you.


Let’s get real. If dealing with fake perfection in our youth-obsessed culture leaves you lost in self-doubt, you’re not alone. It’s hard to stay in touch with your real self in a world where authenticity is in short supply. It’s time to get comfortable in your own skin and decide you are beautiful.

  • Cultivate the courage to embrace imperfection and transform your relationship with yourself.
  • Identify your unique silhouette and shape while learning clever styling tricks to make your quirks and figure realities work for you — no matter your age, shape or size.
  • Accentuate the positive as you give your attention to the best in you and around you.


Accept life’s invitation to live out loud and in color instead of conforming to everything around you. It’s only when you step away from distractions that you can tap into your most creative and authentic self. Live a more inspired life by giving yourself space to think, create, daydream and take moments to step back from your life and observe it.

  • Practice 7 ways to cultivate your creativity and tap into your awe and wonder quotient.
  • Identify your best colors to wear, discover your comfort color and gain a better understanding of why you are comfortable with some colors and not others.
  • Invite adventure and make it a practice to loosen up and lighten up as you make relaxing and have fun a priority.


What are you doing in your life that you know without question is right for you? Is your internal compass pointing you in the right directions to create the life you want to live? Sometimes pushing aside boundaries and obstacles toward a brighter future means making some bold moves to get to know yourself better.

  • Think outside your box and explore the aspects that are keeping you from making empowered decision to stay true to yourself.
  • Choose to live well and stop waiting for special occasions to immerse yourself in quality everyday experiences that make you feel abundant.
  • Make more intentional choices, moment-to-moment and day-to-day to embrace your future self.


We don’t need self-proclaimed experts and daytime television talk shows to tell us how to live our lives. Women have always learned from each other through our day-to-day experiences. Our world is filled with inspiring women from all walks of life, of every age and from every economic and ethnic background. The world is changing, and women are changing as they embrace their vision and follow their dreams into uncharted territory.

  • Define (or re-define) how to own your future as you concentrate on being a woman moving forward, liberated from stereotypes.
  • Recognize and celebrate the role models in your life who despite multiple set-backs and obstacles have inspired and empowered you.
  • Declare your manifesto as an affirmation and a reminder of the values that reflect your unique spirit.


We will celebrate and reflect as you continue to move toward being fully expressed. It’s time to acknowledge all that you have done and summarize the journey we have taken together so far. Because this course is all about YOU there is no ending because you will continue to grow and evolve based on the fundamentals of creating a life you love.

  • Off the Cuff — live YOU & A.
  • Share opportunities for further learning including free on-line resources, recommended reading and paid deep-dives into the individual sections we didn’t drill into.
  • Get inspired to keep moving ahead as we talk about next steps and how you can continue to support yourself and each other in future.


Lifetime on-demand access to Wear Your Life Well Masterclass Training

Showing up live is the BEST way to ensure you get the most out of this training. Chic happens. So don’t worry if something comes up. If you are like me, sometimes taking the time to fully immerse yourself can be unrealistic. The video trainings and webinars are recorded and you can access them anytime.

Weekly Mentoring and Q&A

I’ll be teaching, coaching and answering your PERSONAL questions LIVE on the weekly calls. During each week of the course the calls will be focused primarily on the theme of the week. Ask me anything.

Private Facebook Community

When you connect with your classmates you’ll be a part of a vibrant community of women that is a girlfriends guide to life. It’s a gathering of kindred spirits that is safe and supportive where we can create conversations, laugh, cope and give each other hope — as only women can.

Downloadable copy of Wear Your Life Well: Lessons on the Journey to your Truest Self

I am leading this course based on my best-selling book Wear Your Life Well.  It’s not a self-help book it’s a why -not  book where I share my stories and pass on some of the things that I have come to know about life and style and things I’m still struggling with, working on and trekking toward. 

Downloadable copy of Wear Your Life Well: Your Journey through Journaling

This Dreambook-meets-Lookbook-meets-Workbook is a place for you to discover, dream and do. It helps you craft and clarify your true priorities and set your theme and goals for each week. It will become your trusted companion as you reflect on your own life’s journey.

Exclusive Downloads

Each week you’ll receive Courage Cards — visual reminders that can be downloaded, printed and pasted in your journal or posted around your home to keep you on track. You can also share them to inspire others on your social stream using the hashtag #wearyourlifewell

Personalized Results

Because we are women our stories intertwine, and yet, each of us are as unique as our thumbprint. Life isn’t a one-size-fits-all adventure. The activities in the workbook act as a call-to-guide to jump-start your journey and in doing them you will gain a deeper understanding of who you are, what you want and what to wear.



Course begins January 21, 2018








The Masterclass experience is even better when you take it with a group of friends (or family). Pass the invite along or let your friends know that you’ve registered on social media.








I’m going to give you my all. You need to give it your all. If after 30 days you are not satisfied that you’ve had a breakthrough I’ll give you a refund. But, you need to do the course lessons, actively participate in the coaching, show me the work you’ve done and tell me honestly you haven’t gotten anything out of the experience. Why? Because it’s more than making a commitment to a course — it’s about making a commitment to yourself.