Clothing touches every moment of our lives.

Do you wear your clothes, or do your clothes wear you?

Clearing out my closet with Holly was truly a radically life changing experience. I’ve always known that my inability to let go of certain clothing was deeply connected to core wounds that I’ve carried for far too long. Holly is deeply intuitive and creates a safe container that allowed me to feel the full spectrum of feelings every step of our journey together. She asked questions that help me really get to the essence of why I’ve held on for so long, she gave me permission to feel all of what I felt than gave me the strength to finally release, and let go. In releasing clothing, I’ve released emotional baggage, old stories, belief systems, fears and so much pain.

I’ve freed up so much space both literally but more importantly energetically. I see my closet now and it is a true representation of who I am TODAY, not of who I was yesterday or who want to be someday when I lose the weight, or am bold enough or wild enough. She helped me hone in on my core style statement, THIS WAS SO BIG. When I’m shopping now it’s truly exciting and feels liberating and free and so uniquely me.

This experience felt both deeply enlightening, while also feeling like you are hanging out with a close girlfriend. Our time together felt so judgement and pressure free, Holly is a beautiful guide and this experience has informed my life in ways that were obvious and in SO many ways that weren’t obvious at all. This is such important work. I’m so grateful I gifted myself this opportunity, my greatest wish is that anyone reading this gives themselves the gift of a closet clearing with Holly. You will be so happy you did.

– Jillian Gonzalez, NYC

I see my closet now and it is a true representation of who I am TODAY, not of who I was yesterday or who want to be someday when I lose the weight, or am bold enough or wild enough.

This experience felt both deeply enlightening, while also feeling like you are hanging out with a close girlfriend. Our time together felt so judgement and pressure free…

…this experience has informed my life in ways that were obvious and in SO many ways that weren’t obvious at all.

Working with Holly to go through my wardrobe was a delight. She was professional, friendly, and most of all very, very helpful. She look into account what I do for a living, what pieces I already had, and what the look I was hoping to aim for and really personalized her recommendations. Her recommendations were easy to understand, comprehensive, and spot on. I would absolutely recommend her to any of my friends.

– Corey, NYC

I had the worst time time translating my street style on camera. Holly came in, really listened and helped me get organized and get ready for a photo shoot. The results where perfect!

– Lisa, Los Angeles


I had tried downsizing my closet and identifying staple pieces but didn’t have much luck doing it on my own.

[After this week,] I’m seeing pieces I don’t often wear in a new light, experimenting with things I don’t pull out much, and actually setting style intentions.

I wish I was able to attend more calls and participate in the group more deeply, but love that there was no pressure when I missed a call.
Even though I own a ton of clothes, I didn’t always feel like I had something to wear in the mornings, and often felt like I needed to revamp my closet (or at least my perspective on it). I had tried downsizing my closet and identifying staple pieces but didn’t have much luck doing it on my own.

After this week I have a better sense of what my staple pieces are and feel like I can get rid of clothes I’ve kept simply because they look “flattering.” Plus the two approaches to planning an outfit brought a new appreciation to some of my clothes. I’m seeing pieces I don’t often wear in a new light, experimenting with things I don’t pull out much, and actually setting style intentions.

Starting my morning listening to the audios was probably my favorite aspect of this process. I wish I was able to attend more calls and participate in the group more deeply, but love that there was no pressure when I missed a call.

I think anyone who is looking for a more empowered outlook on their closet would get something out of this experience, but it would be especially beneficial if you’re disconnected from the idea of style or fashion because of any body-insecurity or feelings of body shame.

– Haile Bennett, NYC


Holly helped me take my style ideal and bring it into the real world with actionable steps to start achieving the look I envisioned. I am the best version of myself when I feel good, and Holly helped me start to actualize a wardrobe that makes me feel good everyday.

– Kia, San Francisco

Holly is an amazingly supportive teacher, mentor, and guide. She’s not going to try and shove you into a system or a style or a wardrobe that fits her agenda. She wants you to feel great being YOU. That support and encouragement without a hint of bias is absolutely priceless. I wish there were a million Hollys, and they all taught in the public school system.

– Naomi, Digital Nomad


My closet had too many unworn items that were either old or didn’t fit well (too small, too big, or just never gonna get altered). Because I share my closet with my partner, it’s crowded and so I always felt guilty having unworn stuff. But I also love my more unique and vintage pieces. I purge my closet at least twice a year, but the process often ends up emotional and I keep more than I intended “just in case.”

Since going through this process, I feel less guilt about the number of pieces and more freedom to get rid of things that just aren’t me – I’m slowly releasing the idea of “this may be useful for an audition/certain event” and starting to focus on adding staple pieces that work with my funkier items. This way, I can have my basics and layer on the fun stuff.

My biggest takeaway is that style is so much more conditioned than I ever realized. I always fancied myself unique, but this week showed me that I still have work to do in terms of wearing what I want to wear without concern for how it makes anyone else feel. I am more mindful when dressing for other events in that I am now committed to wearing what feels good and what feels like me – meaning my body feels strong and supported by the clothes I wear, rather than hiding or restricting myself (both physically and figuratively).

– Liz Fisher, NYC

I’m slowly releasing the idea of “this may be useful for an audition/certain event” and starting to focus on adding staple pieces that work with my funkier items.

I always fancied myself unique, but this week showed me that I still have work to do in terms of wearing what I want to wear without concern…

I am now committed to wearing what feels good and what feels like me…

I was hoping this style delve would help me to approach my overhaul more mindfully, instead of playing it safe.

I feel like it’ll be easier than I thought to change my style to fit my day-to-day needs while still honoring my own truth in how I’d really love to portray myself.

Now I try my best to honor who I’d truly like to be in the mornings when I get ready for my day.
I was starting to feel like I’d outgrown a lot of the clothes I have, especially since I’ve been rocking the same gear for some time now. Since my days keep me on-the-go, comfort is an essential part of my look. I haven’t really done any major fashion changes in the past few years, unless you count switching athleisure brands as a major change. It was time for a style overhaul, but I was hoping this style delve would help me to approach my overhaul more mindfully, instead of playing it safe.

Now that the week is over I feel like it’ll be easier than I thought to change my style to fit my day-to-day needs while still honoring my own truth in how I’d really love to portray myself. I’m encouraging myself not to be as reserved about wanting try something different for myself. There are so many ways to ease into making a style change, but it is important to actively facilitate that change.

The fact that I’ve started to put more thought into what I wear in the morning is the biggest change for me. I used to be on auto-pilot when it came to getting dressed. Now I try my best to honor who I’d truly like to be in the mornings when I get ready for my day.

– Adina, NYC


Before this I really didn’t like my closet. There was always this feeling of never having anything to wear, and being “too big” cause lots of my clothes fit when I was much smaller. I’d tried to KonMari a few times and it got rid of some of the gross feeling, but honestly? It never really stayed gone and afterwards I usually just felt like I had less to work with overall. 

When Holly and I had finished I felt a bit more hopeful, and I actually bought a couple of pieces I was missing. Which made a huge difference to trying to figure out what to wear. 

But the biggest takeaway was that often, the game is rigged against you feeling good about what you wear and what you can buy. And it’s worth breathing through that as much as possible and finding the right pieces for you where you are now, not necessarily where you hope to be in the future or who you wished you were. 

Now, I’m more likely to immediately put an item in my donate pile if I put it on and it doesn’t fit right or it makes me feel worse about how I look. Which is a big deal! The other thing is, its so much less angsty choosing something to put on – I have things I know work, my wardrobe tends to all work with each other, it’s a billion times easier to get dressed than before we did this. And I note consistent gaps, now, in a way I didn’t before so that means I can intentionally fill them with something that actually does the job I want it to. 

What I noticed had been missing every other time I’d tried anything with my clothes, that Holly does well, is acknowledging that there’s a lot of feelings and internal thoughts playing out in my clothing choices and as a result of what I choose to wrap my body in. There are connections there that you wouldn’t make without this program and that’s a real loss because, in fact, we spend a lot of time in clothes. They should feel good to us to wear. 

Having Holly around as someone to talk to about is huge! Cause often anything related to clothing is dismissed as shallow and people don’t much care if you buy something new or toss something. Getting to check in with Holly and go through the thoughts that came up and voice problems or points of angst and get clarity on what’s actually going on was extremely helpful and worth it’s weight in gold. 

– Heather Craik, Scotland

When Holly and I had finished I felt a bit more hopeful, and I actually bought a couple of pieces I was missing. Which made a huge difference to trying to figure out what to wear.

Now, I’m more likely to immediately put an item in my donate pile if I put it on and it doesn’t fit right or it makes me feel worse about how I look. Which is a big deal!

What I noticed had been missing every other time I’d tried anything with my clothes, that Holly does well, is acknowledging that there’s a lot of feelings and internal thoughts playing out in my clothing choices and as a result of what I choose to wrap my body in.

Getting to check in with Holly and go through the thoughts that came up and voice problems or points of angst and get clarity on what’s actually going on was extremely helpful and worth it’s weight in gold.

I’m Holly Chayes, I know the power of your perfect personal style.
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Your clothes can either haunt you or help you. We’ll make sure your style is always on your side.
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