A Stylist Reveals The Biggest Fashion Mistakes Women Make

Transitioning your closet season to season is underratedly hard af. Like, tbh, I still haven’t done mine and my room is currently cluttered with winter coats that I’m obvi not wearing right now. However, it’s important to do because it makes getting dressed in the morning a hell of a lot easier. Therefore, given the difficult task at hand, we had to bring in an expert. Meet, Jenny Greenstein, a NYC based stylist who is here to help us with all of our closet transitioning woes, tell us where to shop, and sort out what trends we should be buying.

First, tell me about yourself! A quick career progression run through and what your day-to-day is like today. Also, who are your primary clients?

I’m a personal wardrobe stylist and founder of Your Soul Style. I have a long history working in the corporate fashion industry for companies like Ann Taylor, H&M, and Cole Haan, but always felt called upon to use style as a tool for self-expression, empowerment, and building an authentic self-concept. I didn’t feel that there was space for that in the industry so in 2012, after 10+ years working as an in-house stylist/visual merchandiser, Your Soul Style was born. On the daily, I work with women to define their personal style from the inside out. My goal is to help women enhance and embrace their physical appearance so it is indicative of their unique personality and how they express it. Through Style Coaching, Closet Cleanses, and Personal Styling/Shopping, I assess individual style goals and provide style tips, techniques, and guidance based on what works best for each woman. We also explore the deeper layers, where we look at how appearance is interrelated with the emotional states we experience on a daily basis. I’m commonly referred to as a style therapist. Some topics I cover are: body shape analysis, style personality, self-esteem, shopping strategies, inspiration, motivation, and color palettes. While one of my key areas of focus is the mom space, I work with women at all different transition points. My age demographic typically ranges from 30-45, although I do work outside of those lines.

How do you style clients according to their particular tastes without bias towards your own tastes?

I always remove myself from the equation. While I bring expertise and professional guidance, I’m all about meeting my clients where they are first and foremost, and honoring an individual’s expression. Once I have a solid understanding of a woman’s personal style, taste, and goals, I’m able to offer a roadmap on how to get there. What I put on my own body won’t be the same as what I put on yours. The beauty of style is that everyone’s got their own. My job is to help draw that out.


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it’s been a full week of clients + a beautiful motherhood feature @tribealive (see story highlights, click clients 1,2,3 or features if you care to catch them). while my pregnant ass is tired AF, it’s in these busy-modes where i become so appreciative (+ grateful) for the work i’m privileged to do, supporting women from all different life stages as they discover personal style from the inside out. i am on the continued journey myself and stand beside all of you. while baby 2 arrives in july, i’m still in the throes of the hustle and look forward to more of this incredibly nourishing work, plus a super cool project with @aleen , co-founder of @betches in the coming weeks. so stay tuned as i waddle through them ? #29weeks #stylefromtheinsideout #yoursoulstyle

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What are some of the biggest fashion/style mistakes you see your clients make? What mistakes do you see when they’re transitioning their wardrobes season to season?

The biggest challenge women face is letting go. It’s common for us to hold onto old ideas of ourselves that feel safe and comfortable. We are creatures of habit. But this mindset prevents us from moving forward, and it extends to the style realm, too. In order to evolve, letting go is part of the process, and detoxing our closets/wardrobes on a regular basis to create space for embracing the next iteration of who we are is critical.

The other mistake women often make is holding onto items that don’t fit. Our bodies are constantly shifting, and therefore so is the fit of our clothes. How can we feel proud of our current vessel if we are unwilling to release the outdated version? It puts an unrealistic (and unnecessary) expectation on us to be someone we’re not. And keeping items in our closet that don’t fit can also bring up feelings of shame. 

As for transitioning wardrobes from season to season, women don’t realize how many pieces have the ability to cross over. When we have pieces that work most of the year, there is an opportunity to invest into them in order to get more bang for our buck. 

Are there any winter pieces that can still be worn in the summer? What investment pieces do you suggest your clients buy that work for all year round?

Pieces that work all year round include denim, light sweaters, blazers, camis/tanks (for layering), T-shirts, and most dresses and skirts that are lighter in fabric and can be layered up in colder temperatures. The key investment pieces for all-year wear are: denim, T-shirts, camisoles (for layering), lightweight skirts and dresses (think: satin slip dress) and blazers. All of these items can be reworked to become seasonally appropriate. 


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today I had a conversation with a friend who mentioned that she did a mega purge on her closet. she is a self proclaimed hoarder of all things nostalgic (she’s almost 40 and has unworn pieces from high school) but has come to terms with the idea that it’s time to move on. here’s the deal: when it comes to your clothes, personal style should evolve like you do and letting go is a vital part of that growth process. if you’re holding on to a past self, there is no space to embrace a current and progressed version. while we all have timeless and classic items that shall remain (just like we retain certain parts of ourselves), there are always things which need to be re-evaluated and released. the only way to ensure your inner self aligns with your outer is to carefully examine these visible extensions as we move through life’s transitions. need support? link in bio to learn how i can help you with the process ? #letgo #stylefromtheinsideout #yoursoulstyle

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How do you transition trends season to season? (For example, the neon trend, which we started to see this past fall and is huge for summer as well.)

Trends are tricky because they are short-lived and don’t last much longer than one or two seasons. I think it’s fun to play with trendy pieces and build a wardrobe that includes them if that aligns with your personal style, but I don’t suggest investing financially when we know something is about to come and go. While I don’t love the idea of fast fashion brands because they aren’t sustainable, they are key players for trends. To make it more sustainable, I suggest brands like Rent the Runway for short-term wear without increasing our carbon footprint. 

What are some of your favorite high-end brands? Some of your favorite fast fashion brands? Some of your favorite places to shop for your clients?

My personal favorite high-end brands are Love Shack Fancy, Ulla Johnson, and Mara Hoffman. My personal favorite fast fashion brands include Zara, Mango and H&M. I do try and shop ethically as much as possible and that continues to evolve over time. When it comes to my clients, I take them to department stores like Bloomingdale’s or Bergdorf Goodman to curate items from a range of brands, and when it comes to e-commerce it’s Shopbop, Net-A-Porter, Matches Fashion, or Revolve. Each client is different, so I don’t decide on where I’m pulling from until we meet in person and start to build a relationship. 

Are there any big trends for this coming fall/winter that we can/should start shopping now?

Pre-fall is already in trickling in, but it’s difficult for women to start shopping for the next season while just in the beginning of one. I also need to say that while staying informed about trends is relevant, it’s not the driving force in my work. That said, some to watch out for this fall/winter 2019 are: feathers, power shoulders, satin (keep your slip dress handy to pair with layers this fall/winter), statement coats, pantsuits, plaid (preppy), and fleece.

Images: yoursoulstyle / Instagram; Brooke Cagle / Unsplash

Shannon McCormick
Shannon McCormick
Shannon McCormick (previously under the alias of 'Betch Dressed') is a self-proclaimed fashion expert with a sick obsession for all things Bravo. She primarily writes about everything fashion, but also dabbles in other areas because she's a talented overachieving Virgo. Follow her on Insta (@shanmccormick) and comment/DM topics you want to hear her incredible take on next!