Confessions of an Organizer: Hiring a Stylist

25 Sep Confessions of an Organizer: Hiring a Stylist

People expect organizers to be perfect 100% of the time, but (I’ll let you in on a little secret) no one is ever perfect 100% of the time. Organizers – like celebrities – are just like everyone else: we put our pants on one leg at a time. Often we’re put on pedestals by clients because we can do something that many people find tedious or difficult: we can organize and keep things organized thanks to custom tailored systems. But I swear, we’re just like you.

Case in point, I hired a stylist.

Part of my reasoning was that I needed to test the services of two women to make sure that they would be a good fit for certain clients. As an organizer I have a large resource list, and I’m not the best at telling clients what colors look best on them, or how to wear certain items for their shape, but I can make your closet look like a specialty boutique designed just for you. And honestly, I also hired her because I’m now in my late-thirties and it’s high time I started dressing like it. I’m having a bit of an identity crisis, truth be told. I still have clothes from my 20s, but then other times I’m dressing more like someone in their 40s. Basically, I’m lacking a distinct style and it showed.

I know part of that has to do with losing my mother – the one who did know about fashion and I relied on so much to help me with looking put together – when I was in my early 20s. I was then left to seek advice from friends, colleagues or even the sales people to help me find my identity. If you ask my friends and family they’ll say I have a cute and unique style, but it feels very safe and undefined. Needless to say, I’m ready to reinvent myself now that I’m feeling super confident in both my personal and professional lives. I’m ready to rebrand – so I called in reinforcement help.

I ended up working interviewing two different stylists (both I had met through networking groups) which was great because I had options for my clients.

My three hours with Stephanie Stimmler of Venita Textiles were fascinating. Stephanie has a background in fashion and a great trendy fashion sense. I think she’s going to be a great fit for my more stylish and fashion forward clients, and maybe even those who have that desire to “level up” in their fashion game. I took in a lot of information and learned a lot that I had never thought of or considered before. And I had a better understanding of how my clients feel when I’m working with them.

We began by reviewing an impressive online style survey I had filled out in advance of our session, and giving a bit of a background to Stephanie about my current style and what I aspired to dress like. We then dug into the closet and she was honest, which may have felt brutal at first, but it was really great (this must be how my clients feel). Now, I don’t have a lot of clothes to begin with (compared to most people), and by the end of the session more than half of my clothes were on the ‘get rid of’ side of the bed. Some of my favorite items were in that pile, and I wasn’t ready to let go. Sound familiar?

Stephanie understood this and we talked through some of the items. She explained why the top wasn’t best for me: the fit was off, the coloring washed me out, it was too junior or dated, etc. Some of it I could see and it helped me to let go. Some of them I just wasn’t ready to part with, and that was ok. Sometimes we need time with a decision, but the seed has been planted. Plus, I didn’t want to be left with only a few options to choose from, and the need to have to go out and spend a lot to buy a whole new wardrobe. “But you wanted a capsule wardrobe,” Stephanie reminded me. True… but… baby steps.

I also worked with Anne Ferris of Wardrobe Savvy for several hours during our initial consult. Like Stephanie, Anne had selected some pieces she thought weren’t great for me but I loved that she thought I could incorporate more of what I already had, adding in a few staple pieces here and there to make them work better. I didn’t feel the need to go out and buy a lot (which is always good) and I was able to shop my closet more which is also what I aim to help clients do. She showed me how to pair pieces together that I never would’ve put together. It was a great education.

Anne and Stephanie were both great for different reasons. I was super impressed with Stephanie’s on boarding questionnaire which really got me thinking about my style: what it was and what I wanted it to be. I appreciated her knowledge from the fashion industry, but didn’t feel hip enough to be using her talents (this stems from my own insecurities). I have since referred her to several clients who have been very happy with her results. With Anne, it felt like a more laid back approach and those baby steps I needed to work on my wardrobe piece by piece over time and with a tighter budget. She didn’t push me to go out and buy a lot all at once, but rather encouraged me to add in and build my wardrobe over time. Personally, this felt like the right approach at the time.

So see, I’m just like you. I’m open to letting go and revamping my style. But I’m also budget conscious and can’t purge it all in one sitting, just to go out and by all new stuff next week.

But whenever we’re ready for a change, that change can be scary and a bit overwhelming at first. So I leaned in. After my consults, I put a few pieces back into my closet, and promised to let them go when I felt that I had suitable replacements (which I have). And I hear this all the time from my clients, so it wasn’t all surprising when I found those same words escaping my own mouth.

At the end of each session my neatly organized studio was quite a mess, but I also felt energized. Here were these professionals who knew what they were doing and had me motivated to let go and rebrand. That’s what I wanted after all. And I had to let go of some items so that new ones can come in (the one-in-one-out rule of organizing) and a new me can emerge.

I ended up working closely with Anne. We went shopping together 2-3 times, and she’d pull out things I wouldn’t think of, and she’d help me make it an outfit instead of just clothes I threw together. What I noticed was that my confidence really skyrocketed when I felt put together and polished. I felt like I had more of an identity, and I learned enough that I knew what to look for when on solo shopping sessions. I listen to my own opinion now, rather than relying only on friends or the sales person, because of the education I gained from working with a stylist (just like I aim to educate my clients as a professional organizer so they can continue to have organizing success). I’ll definitely work with a stylist again when I feel I need assistance with finding some key pieces, and helping me to get out of that comfort zone.

If you’ve ever considered working with a stylist but have been worried about the expense, I understand. We invest so much in our looks already (haircuts, manicures/pedicures, waxing, facials, botox/fillers, makeup, etc.) that wouldn’t it be wise to find someone who can make sure we’re making the right stylistic decisions? Someone who can see the potential in us and help us to understand what looks good on us and why? Someone who can educate us so that we can go shopping on our own and find great pieces, and learn how to mix and match? Is it really any different from investing in a personal organizer? Or cooking classes? Or in financial planning? In each we ask the professionals to share their knowledge so we can do it on our own, but with the ability to still come back and ask for help.

Interview a few stylists to make sure that you find one that fits with your specific needs. Reach out to Stephanie or Anne, or search for personal stylists in your area (a simple google search, or check Nextdoor or at a local networking group).

Take it from me: refreshing your brand through your clothes does amp up the confidence and that can only stand to benefit you. Yes, it’s a financial investment but hopefully the knowledge you gain will stay with you over the long run, and you’ll invest in staple pieces of quality that will last many, many years.

Have you ever hired a stylist? What was your experience?

Are you a stylist reading this? What great tips can you share with readers to get started?