How Working with a Stylist Broke My Creative Rut

Finding blind spots and regaining my closet spark 👗

Getting dressed has always been a creative outlet for me, a daily practice of expression and imagination. Since toddlerhood, putting together fun outfits has been something I enjoyed, graduating from princess dresses to pattern-clashing. After experiencing some light bullying in middle school, I realized I was not like the popular girls and would never feel comfortable in a ponytail and khaki capris. It was through fashion that I started to express my authentic self. It was so FREEING to stop trying to dress and behave like other people and to discover my personality through clothing.

Throughout adulthood, like many of us, I’ve found myself falling in and out of deep fashion ruts and style droughts. Especially rediscovering my style in a post-pandemic, post-party-girl, work-from-home world. But in the last year, I’ve been feeling more and more STUCK. I’ve had a relatively clear idea of the direction I want to go in, but have been overwhelmed and unsure of how to get there. It’s frustrating when something that has been a consistent creative well runs dry.

Enter my Instagram-turned-IRL friend, Jordy Scheinberg, an innovative costume designer and wardrobe stylist.

Jordy on Instagram

I’ve been a longtime fangirl of Jordy’s work, starting when we overlapped working at Nickelodeon. She has created the sartorial tone for music videos, shoots with some of my favorite photographers, and movies and TV you’ve definitely seen. She has an incredibly playful style that she can manipulate across genres and media.

I’m a firm believer in admitting when you need help and in paying experts to do what they do, so when she was on a recent break between projects, I asked if she could help me reinvigorate my wardrobe. I wanted her guidance to find ways to elevate my daily looks and identify blind spots in my wardrobe, but I also viewed it as a creative retreat, working with a specialist to help spark my sartorial imagination.

Some of what I learned were refreshers, and some were things I’d never thought of before, but all of it was stuff I needed to hear and think about.

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The first step was for me to create moodboards (twist my arm), collecting looks that appealed to me. I dumped everything I liked onto a couple different pin boards here, here, and here, then we met for coffee and reviewed them. Jordy was instantly able to find common threads (no pun intended) across all the pins and ask me questions. It became rapidly clear what I was drawn to and what was missing from my closet.

We discovered a lot pretty quickly. I liked the Copenhagen-girly layered looks and was drawn heavily to menswear (trousers, vests, tomboy style). I was ready to embrace accessory overload and chore coats. There were also surprises when it came to identifying patterns - despite the fact that tons of images I’d saved included white tees, I didn’t own any. Or that even though belts played heavily into looks, I’d saved, I never wore them.

“You seem to be drawn to vests, there are a lot of them in here, how many do you currently have?” None.

“There’s a decent amount of leopard print across the boards. Do you have much of this in your closet?” Not one piece.

“These outfits seem to be mostly paired with sneakers. How often do you wear your Sambas?” I literally don’t even own a pair.

We didn’t meet again for about a month, and in that time, I scoured the moodboards to find patterns and commonalities that were now coming into sharper focus. I started hunting down specific items for my closet based on what consistently reoccurred across the boards.

Which leads me to the next thing I learned…

Step two of working with Jordy was for us to go through my closet together. This was wildly helpful for several reasons, but the biggest was that it helped me hone in on individual pieces I was missing from my wardrobe.

As we started pulling hangers out, Jordy noticed I had a lot of matching sets and asked how often I mixed them up with other clothes. I realized… I didn’t. That revealed two things: One, I had a bunch of great pieces just sitting there, only ever used as part of a set. And two, I’d been shopping with complete outfits in mind, instead of building a wardrobe of versatile, mix-and-matchable items.

I’d been looking for specific ensembles, not thinking about my closet as a balanced whole. I began to realize the value of investing in intentional pieces that complement what I already had. It’s kind of like building a kitchen: you don’t buy single-use tools every time you cook, you stock up on versatile spices and ingredients that let you create totally different meals.

Now, when I look at outfits, I no longer see them as fixed, head-to-toe packages. I scan for what makes them work: the base layers, how things are proportioned, how pieces are paired with each other, and which elements can be reimagined across different looks.

“How about you try this t-shirt on under that sundress?” Jordy said.

She was holding two items up that I never in a million years would have paired together. Historically, I don’t love dresses because of their lack of versatility, but here she was proving that a little bit of layering creates an entirely different outfit. Throw a vest on top, and it’s even further transformed.

I realized I was associating layering with cold weather, but this process helped crack my mind way open to the countless combinations of layers that can work in any season. Now I think about layering with every new item - how can I layer this with other pieces, and what unexpected item would look cool to wear this over or under?

A roundup of about half the outfits I wore on my trip

When Jordy came to help comb through my closet, she suggested we get specific and focus on packing for my upcoming trip to France. She told me that when she travels, she likes to pick three core colors as her palette to build around, to make getting dressed on the trip feel effortless while staying cohesive.

As we went through my clothes, we realized - both in what I was planning to pack and what was already hanging in my closet - that I essentially have already chosen a color trio without realizing it. I’m basically a Blue Sun, Brown Moon, Green Rising.

I discovered on my trip how insanely helpful it is to have all your items complement each other. Despite only bringing a carry-on, I felt like I had countless options because I could essentially pair any of them together.

I’m not talking about finding your cuts in a ‘90s women’s magazine kind of way - no Dresses to Flatter Your Pear Shape energy here. I mean it more in terms of what you naturally gravitate toward, or reach for without even realizing.

There are so many directions you can take with even the most basic of items - Take the classic white tee. I’m a baggy tee gal. Not Billie Eilish shapeless, but not form-fitting or babydoll cut. I’m drawn to a straight, boxy cut with sleeves that hit mid-bicep and a crew or lightly scooped neckline. No V-necks, no muscle tees, no cowls, no bateau.

Jordy also got me paying attention to fabric weight. As we looked through my most-worn tees, we noticed almost all of them were vintage: thick, soft, and broken in. This revealed that I prefer a heavier-weight cotton, usually combed or ringspun.

Your style isn’t just what you like in a photo; it’s what you like on you.

At times, this process was not dissimilar to working with a therapist or life coach: it helped bring me back to myself. Working through my closet intentionally helped surface blind spots that are obvious to an outsider but take a few breakthroughs to recognize on your own. I realized I’ve been reinforcing a collection of imagined narratives about myself for the last 20 years.

It was eye-opening to realize how many mental blocks I had around getting dressed. There were so many things I liked but didn’t think I could “pull off” because of my age, my body type, or not being the right vibe. I didn’t own leopard print because, in my mind, that was reserved for “cool girls,” a category I didn’t see myself in. When it came to having fun with daily outfits, there was a fine line between looking too kooky like Miss Frizzle, or like a try-hard in an attempt at street chic. At one point, I even said out loud that I hadn’t worn certain sneakers because I thought my “body would look weird with a narrow shoe.” Even just saying some of those old beliefs out loud helped me see how nonsensical they were and finally let them go.

I needed to stop thinking about what I was doing or who I was seeing in my clothes, to focus on how I felt in them. I’m not trying to attract or impress anyone, and maybe even more importantly, I’m not comparing myself to anyone - I only need to dress for ME. I don’t need to be Carrie Bradshaw or Katherine Hepburn, I want to dress in a way that makes my younger self feel excited to grow up and my older self look back and think, “She had fun.”

I’m excited to break these arbitrary, societally induced mental rules I’ve built for myself and to tap into a version of myself who wears whatever she wants.

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At a basic level, this process got me excited about clothes again, but beyond that, it broke down some mental and creative barriers I’ve been struggling with - some consciously and some I hadn’t realized. Building an outfit that makes me feel confident is an act of self-care, and experimenting with clothes IS a daily act of creativity.

I’m looking at colors and textures in a whole new way. I’m scanning the world around me for constant inspiration - a colleague’s double-layered tees, vintage patterned tiles, my 4-year-old goddaughter’s homemade jewelry. I’m making moodboards and scanning magazines and taking the time to experiment.

Who's a leopard print girly NOW?

Wherever you’re at in your own wardrobe journey, I encourage you to widen the aperture and think about what’s missing in your process to make it feel more inspiring. It might be as complex as talking in therapy about why you feel like girls with straight hair can pull off things you can’t (just hypothetically speaking….), OR it might be as fun and straightforward as buying a pair of pink sneakers.

How we dress is an extension of our personalities, our bodies a blank canvas for daily expression, and if you feel inspired by what you’re wearing, it will inevitably help you find further inspiration everywhere else.

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