When you really think about it, combining style with your emotional being, really makes sense. When you feel great, you exude confidence and look “put together” on the outside. When you feel down, you run around in oversized sweats and hide under a baseball cap (at least we do!). Heymama member Jenny Greenstein is the founder of Your Soul Style and has merged her extensive career in fashion with her passion for emotional well-being into a unique (and booming!) business to help women look and feel like their best selves. Our very own co-founder Katya Libin was lucky enough to experience her infamous Closet Cleanse first hand and we learned how Jenny approaches the process with her clients and why this method to personal styling may be the most well-thought out yet. Read on…


Personal Styling Strategy with Jenny Greenstein


We love how your business incorporates style with mindfulness. How did you decide to meld these two concepts?

Your Soul Style developed organically, and while things didn’t formalize until 2013, the seeds were already planted. Style and emotional health are big areas of focus for me, and I realized after moving through my own major life transitions, that overlap is inevitable. I fancy myself a stylemaker from the inside out, and I use style as a vehicle to empower women to be their authentic selves. Life can be challenging, but how we show up matters. I believe true style works from the inside out and not the other way around.


How did you get into personal styling?

After 10+ years working in the corporate fashion industry as a stylist/visual merchandiser, combined with a semester working towards my Masters in Social Work at NYU, I created Your Soul Style and began personal styling. While I appreciated my time working for major retail brands, I felt compelled to do something driven by purpose as opposed to bottom lines. To me, style has always had a deeper meaning than what’s popular amongst the masses. It’s a very individual experience and everyone’s predisposition is unique. It’s so vital to honor that. Combining my passion for style in both the tangible sense and emotional sense is a natural fit.



Why do you think a women’s style changes so much after she has children?

We don’t take that many sharp turns in life, but there are a few monumental shifts that do occur, the transition into motherhood being one of them. It sounds cliché, but becoming a mother is as much of a rebirth for the mama as it is a birth of a baby. Everything changes in your emotional, physical, and mental self. If you immerse yourself authentically in the journey and hold space for vulnerability, there is an undoing of the self, before you are able to embrace the current version. Style plays into this process.

It is just as important to understand how you show up stylistically to ensure the most authentic, empowered and confident version of yourself is present.


Why is a stylist an important investment for every mama?

Personal style typically falls lower on the totem pole of essentials when we become mama’s, but is an act of self-care. In the same way that women go to therapy, meditate, eat a healthy diet or go to the gym, it is just as important to understand how you show up stylistically to ensure the most authentic, empowered and confident version of yourself is present. Since a women is going through a major shift when entering mamahood, seeking support in an area she is struggling is key.


Why do you think clothing is such an emotional part of a woman’s life?

Style is a reflection of who we are inside and when there is a sense of disconnectedness to the inner self, that comes through in how we dress. This is why I created Your Soul Style. It is so essential to have a strong and confident sense of self, before that self  is represented externally. When a woman feels emotionally unsteady, it comes through in all forms of self-expression. It’s unnerving, to say the least. Personal style is also something that considers our physical body. There is a lot of cultural pressure to look a certain way, and be a specific size, and as a women goes through physical transformations, especially in motherhood, it can all feel overwhelming and unattainable. The other piece is that clothing symbolizes moments in time and we emotionally connect ourselves to these items. The same way a scent can take you back, so can a pair of jeans. And you may have been wearing those jeans at a super challenging time in your life. Like all toxic things, this is an indicator for release.

Heymama left image
Heymama right image

What are your thoughts on trends in a mama’s wardrobe?

I’m neutral when it comes to trends because style is driven by the individual person. I do find that as women get older they establish a comfortable sense of personal style and stay close to that line. This is not to say that incorporating trends is off limits. But style becomes less transient the more you settle down.


What are five go-to pieces that every mama should have?

A black blazer: to be worn casually with jeans and a t-shirt or elevated with leather pants and heels – a black blazer is a go-to piece in a mama’s closet. I love this tuxedo style from Theory.

Fashion Sneakers: Fashion sneakers go the distance, and are both stylish and functional. Every mama needs a pair to one-up her standard running shoes. I’m loving the sustainably made options from Veja.

One-Piece Dressing: Whether it’s dresses, jumpsuits or overalls, one-piece dressing makes morning routines super easy, but super stylish! I love these overalls from Reformation and this day to night dress from Free People.

A go-to carryall bag: A carryall to house both mama and baby’s gear is key, so keep a stylish and functional option on hand like this gold luxe backpack from STATE Bags.

Hats: Mama doesn’t always have time to tame the mane, so a few stylish hats to pull from is key. I love the entire collection from Janessa Leone.

Heymama left image
Heymama right image

Tell us more about your closet cleanse service. It sounds amazing!

Through a one-on-one Closet Cleanse, we will move through your closet together and DETOX, get organized, and set you up with an edited wardrobe that you feel good about. We will ask questions like, “When is the last time you wore this?”, “How do you feel when you wear this?”, “Does this item really fit anymore or are you saving it for when you lose/gain weight?”, “What motivated you to buy this?” and then we evaluate organizational strategies and establish best practices. A Closet Cleanse is especially emotional for new mama’s in the postpartum phase. The dramatic physical shift, the unsteadiness of new-mom life, combined with the general overwhelming emotional experience- it’s an extremely cathartic process and a necessary one after baby arrives. Shedding and creating a new foundation for this “new normal” life is essential.


Do you find that this process is always emotional?

Pretty much, yes. Women (and people in general) are most vulnerable in the in-between phase of life. It’s a growth period, a stretching, and I believe that in order to authentically evolve, we must experience the “growing pains” of that.


Heymama left image
Heymama right image

Tell us about YSS Shop!

Oh, oh! I love my YSS Shop! I’ve forever wanted to open a brick and mortar boutique (to come, maybe?), and the YSS shop gives me a space to curate an assortment of my latest and greatest finds, with the Your Soul Style aesthetic in mind. The visual direction is for the classic, laid back, edgy, bohemian and urban sensibility. Silhouettes are free spirited, forgiving, and most will work on different body types for the changing phases of your life. Prices range from high to low, and I pay close attention to featuring as many socially responsible and sustainable brands as possible. The shop continuously updates based on trend, end-use, and seasonality. It’s the perfect destination for mama’s whose personal style aligns closely to Your Soul Style.


What are some of your daily self-care practices?

I wish I could say that I hit yoga 5x a week, but that is so far from the truth. I hit strides here and there, but with no real overarching consistency. I’m way better at mental exercise than I am at physical. I am actively in therapy and have been for 20 years. Other self-care practices include: flossing, choosing my daily looks the night before (even if in my head!), and eating healthy foods.


What is your morning and night time routine like?

My wife and I take turns playing with Vida who wakes at the crack of dawn. It’s not the most sexy entry to the day, especially since I’m more of a night owl than a morning person. I drink a coffee as fast as I can get one down, shower, apply sweet almond oil, santal 33, do my hair, get dressed, (always) make the bed, apply minimal make-up, make Vida breakfast, play some more and head out once our nanny arrives. I used to take Vida to coffee (for me) and a bagel (for her), but since she hit two, getting clothes on her before 9am is borderline impossible. My nighttime routine is simple, take contacts out, floss, brush teeth, facial oil and done. I really want to pay more attention to all the incredible non-toxic anti-wrinkle face regimen but I keep it simple (for now).


Check out more about Jenny and her services at Your Style Style here.

3 pearls of wisdom


Throw away your parenting book and meet your child where they are.


Always remember that your child is not you, but an incredible, unique and amazingly separate person.


Hold space for your child to be just that, a child. Growing up is really hard.

xx Jenny Greenstein
  • Share
Close image

leave a comment

Your email address will not be published. Required fields are marked *

HeyMama Welcome Offer | $50 Off

arrow-right pointer circle facebook instagram linkedin pinterest-brands social-youtube twitter-brands