Our affordable monthly style subscription that helps you say good-bye to closet stare-downs while keeping your style seasonally fresh, modern & fun!

Summer 2024 enrollment is now closed. To be notified when enrollment opens again, please join our waitlist below.

“Insiders is my monthly magazine subscription on style that is interactive and personal. I used to collect every style magazine to garner a perspective…this program blows all that away!!!”

– Fran L.

A Personal Invitation to Join Us
Are you ready to embrace life with more style, grace and joy?

Having one hour reserved on your calendar each month to focus on a day-to-day wardrobe that works for your lifestyle allows you to feel more energized and confident while experiencing life with deeper satisfaction and joy. We keep it real, providing tips and resources that anyone can implement right away.

This special group is full of women just like you:

  • Mid-career professionals interested in keeping their wardrobe on track both professionally and personally
  • Empty nesters focused on self-care, including learning practical ways to make everyday style easy and less stressful,
  • Women celebrating retirement who have no intention of giving up their style
  • All women navigating the excitement of travel, upcoming family events and next chapters on their own terms

Insiders literally takes you on the inside with us, giving you more access to our team to help guide you through each season of your style. It’s truly a gift to give to yourself. You’re worth it!

“My initial reason for joining Insiders was to have a more thought-out approach to my wardrobe. That goal was met right away. What has surprised me is how much money I am saving. In the past, my impulse would be to buy something new before visiting my closet and deciding if a new purchase was warranted. As simple as it may sound, this has been a big shift for me, saving me not only money but time too.”

– Jayne M.

What's in Store When You Join

  • Monthly Live Coaching and Q&A: Join the Dressing Well Team the first Monday of each month from 7-8 pm for exclusive content not available anywhere else. Fashion show & tell to help you “shop” your own closet and plan “new” outfits as well as an interactive breakout room activity with other members and Live Q&A is all part of the monthly fun.
  • Replays of All Live Coaching Calls: Never worry about missing a session. Catch up at your convenience.
  • Curated Shopping Links: Receive inspiration and cut down on shopping time and expenses with carefully selected links tied to each program topic to consider after each coaching call.
  • Insiders-Only Facebook Group: Connect with like-hearted women, share resources, and get real-time feedback on outfits.
  • Special Bonuses: Anticipate some prizes (& surprises!) along the way. We love to delight!
Other Reasons to Join Us

Unbeatable Value: Monthly Membership ($24.99) or Annual Membership ($249 – get two months free with this option). Gift certificates are also available for annual memberships.

Get Started Right Away. Once you enroll, you’re in! There are no complicated membership portals. You don’t even need to be on social media! You’ll be sent a welcome email with the program calendar, zoom link and invitation to join the private Facebook Group as soon as you join! You’ll also be sent a fun questionnaire to help us get to know you better.

Flexibility: Continue your membership as long as Dressing Well Insiders adds value to your life. Unsubscribe anytime. We wholeheartedly believe you will love the program. This policy is in place to be sure it stays relevant to you.

No Catch: This isn’t your typical membership – it’s a unique opportunity crafted for our cherished community who have expressed a desire for an extra layer of style inspiration, motivation, and fun with our firm. It is what we do best and this program allows us to do it with more gusto.

Subscription Options

Join Us on the Inside Soon!

Summer enrollment is now closed.
To be notified when the next enrollment period begins, please submit your information below.

Monthly Subscription



per month

Annual Subscription

Get two months for free!


per year

Why People Love Insiders
"Thank you for bringing the Insider program to life. I’m no longer alone in my quest for wardrobe nirvana. I feel a real connection to others in the group, learning so much from all of them too. I was not expecting that. These sessions are a powerful tool in helping me stay focused. Both the content and community are inspiring."
– Joanne A.
"Being in the Insider group is like having a girlfriend on call. I can post something in our Facebook group and ask an opinion and get great feedback on an outfit, shoes, anything!"
– Karen W.
"Mary Lou hit all the points last night. It was such a great demonstration of how wonderful the program is. I just loved it. I really do feel the camaraderie…and I appreciate that you can participate in the way (and price point) that works for you.
– Fran L.
"I find myself laughing and experiencing so much enjoyment from each session. Revealing your best tee-shirts are from Costco, your own weight gain not holding your style back, that date night is mostly on the couch watching Netflix, you KEEP IT REAL - and that's why you're so loved!!!!!!"
– Lisa L.
"Although I have not been able to attend the sessions live, the replays are all I need to keep my wardrobe fresh and moving forward. What a unique and valuable offer this is. The monthly shopping links are also really fun. I have added some wonderful pieces to my wardrobe that I would never even known about without this program."
– Cassandra F.
"I’m so grateful for this group. I feel so much more confident in my appearance and am wearing things in my closet I have not considered for years!"
– Linda H.
Frequently Asked Questions

The monthly coaching sessions are delivered live on Zoom by Mary Lou Andre and Senior Stylist Sarah Zengo, giving you the opportunity to interact with them in real time. Can’t make a session? No worries. The recordings are delivered to your inbox within 48 hours. There is no complicated membership portal for this program. Email is all you really need. Our programs are easy to view on any computer, tablet or smartphone.

While the program does come with a private Facebook community for members to share resources, get feedback on outfits they post and showcase personal wardrobe wins in between the live monthly coaching sessions, Facebook participation is completely at your discretion.

At its core, this program is about helping you stay on track with your style month-to-month and season-to-season with ease in a way that is comfortable for you. Some members never miss a monthly live session as the interaction with a group of like-minded others and Mary Lou and Sarah is part of the joy of the program for them. Others keep up with the monthly content by viewing the replays at their convenience. Your activity within the private Facebook group that comes with membership is at your discretion as well.

The monthly live coaching sessions are held for one hour the first Monday of each month from 7-8 pm ET on Zoom. We run a tight ship. Doors open at 6:55 and we wrap up right at 8 pm. If you choose to watch the recording, it will be about 45 minutes as we trim each replay to cutout the 5 minutes of folks entering the zoom and the 10 minutes break out room activity which is a private exchange. The group Q&A and session wrap up are all kept intact on the recording as they provide extra wisdom and motivation.

The breakout sessions add extra interaction and idea sharing between members and are very popular. We reserve 10 minutes for this fun activity during each live session. Ahead of time, you are given the breakout room topic and encouraged to come ready to share an idea and/or something from your closet as part of the discussion with others in your breakout room. Each breakout room has 5-6 members.

We have Q&A monitored and answered by Senior Stylist Sarah Zengo in the Zoom chat log throughout the entire 60-minute live sessions. She is a pro! Mary Lou’s 10 minutes of Live Q&A at the end of each session is organized and facilitated by Sarah, ensuring all questions are answered.

Yes! We send out monthly emails to announce each month’s topic. We also send a reminder email at noon the day of each session. Both emails include a Q&A link to collect questions for those who cannot attend.

After every live coaching session, we get to work on your behalf, shopping the internet for 10 items and ideas that resonated most during the fashion show & tell part of each session. We focus on affordable brands that offer a wide-range of sizes, colors and styles to best match membership needs. We also include links to some of our favorite, lesser-known websites that Insiders love to know about. The shopping links add excitement to the program. Who doesn’t like to receive the gift of curated style in their inbox once a month!

Insiders was created in response to many of our clients, group program graduates and members of our Beyond Dressing Well Facebook community asking for an enhanced version of our 30-minute Live Show to keep their wardrobe even more seasonally on point with more ongoing access to our talented team. Early response to Insiders has been so strong that we are now scaling back the Live Show from a weekly to seasonal program so that we can focus more energy and creativity on Insiders as our premier monthly style club offering.

Advances in technology allow us to go much deeper with you on your style journey as an Insider than what the Live Show format allows. In addition to providing brand new monthly content not available anywhere else, Insiders also offers a unique coaching and interactive platform with us and other members. If you like the Live Show, you will LOVE Insiders!

No. Membership is open to all. Many of our private clients love Insiders because it keeps them focused on their style between in-person personal styling appointments and other programs and courses with our firm. Like everyone else in the group, they also enjoy a monthly dose of live style inspiration in a group of like-hearted others!

That is not necessary at all. While many Insiders have taken our popular 90 Day program and/or the self-study program, Insiders runs completely separately from other firm offerings.

Each monthly coaching session is delivered live by Mary Lou Andre and Sarah Zengo. We record these sessions in case you miss a session or want to refer back to them at your convenience. They are emailed to you promptly for easy reference.

There is no long-term commitment. You can cancel anytime if the community doesn’t not feel like a great fit for you. While we wholeheartedly expect that you will love the program, this policy is in place to ensure the program stays relevant to you.

For monthly subscriptions, your credit card is charged the day you enroll. After that, the card you used to enroll will be automatically charged every 30 days for as long as you choose to stay a member. You can always change the credit card you would like charged by reaching out to us at info@dressingwell.com. We will send you a link to change your credit card.

For annual memberships, your credit card is charged the day you sign up. At your one-year anniversary, your credit card will be charged again so that your membership is not interrupted. We send a reminder that your card will be charged again 2 weeks before renewing annual memberships.

The ROI is very significant. Whether you attend the coaching sessions live or watch the recordings, you will be encouraged to use what you already own in more effective and interesting ways, breaking you free of the dreaded, “I have a closet full of clothes with nothing to wear!” syndrome we all face from time to time.

You will be encouraged to let things go that are no longer serving you (we even make this fun!) while understanding how color, fabrics, accessories and combining pieces (many of which you likely already own) can enhance fit and flair. 

When you do need to freshen things up to keep your style modern, we will help you pinpoint what is needed and how to cost-effectively shop for these items. Many members tell us that the monthly curated shopping links alone more than pay for membership as this feature helps them confidently decide what to add to their wardrobe without second guessing themselves or overspending.

We designed this program to appeal to many different types of people who enjoy our brand of style advisory. The group setting provides a cost-effective vehicle to receive current, relative, cost effective and easy to implement information each month that will keep your style on track and moving forward in between (or as an alternative) to individual, private styling sessions with our firm.

Yes! We offer gift certificates for annual membership. Follow this link to order!

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