We learn to dress ourselves around, what, kindergarten? It's not hard. You put garments on the parts that you don't want to get cold and that's it. Back then we didn't give much thought to how we looked in our clothes — or maybe it's that we didn't give much thought to what other people thought.
But somewhere along the way choosing clothing became a despair-inducing exercise. How does this look? What does it say about me? Is it in style? It is too young or too old for me? Does it fit? Some of us may respond by overbuying, stuffing our closets with things that don't quite work; others by giving up and wearing the same things on repeat. Either way, getting dressed ends up a miserable affair.
That's where I found myself, five years after trading a conventional go-to-the-office job for the freelance, work-from-home life. With great relish, I had donated my “work clothes.” But with no dress code, and nowhere to really go every day, I couldn't justify the expense of buying clothes. Besides I'd never liked shopping anyway.
But guess what: even writers leave the house sometimes. And when I needed to appear in something other than my bedraggled wardrobe, I'd frantically scour a clothing store and buy whatever met some vague interior algorithm of affordable and not awful. Except sometimes it turned out to be awful.
Meanwhile I held on to the remnants of my old wardrobe and ultimately built a chaotic mess that made my blood pressure spike every time I stepped foot inside my closet. I'd wear the same thing two or three days in a row just to avoid making decisions. A daydream began to loop through my head: what if I just throw it all out and start from scratch? How freeing would that be!? But I didn't have the nerve, know where to even start, or want to spend that kind of money.
Finally one day it clicked. I'm a big believer in hiring people who are more knowledgeable than I am to do things I'm not well-equipped to do — I hire a professional to prepare my taxes every year, for instance. I'll also spend money to save time. There are people in this world who know how to pick out clothes that best suit a person. Why not turn to an expert to dress me?
Once I let go of the idea that I should be capable of this task and embraced handing a loathsome responsibility over to a pro, I got really excited. Especially when I came across an article about stylist Laurel Kinney. She had studied psychology and came from a social work background. This comes in handy, she tells NBC News BETTER.
“So many things can come up when you're going through the process of deciding how you want to present yourself,” she says. “Identity, financial stuff, 'do I deserve this?' People have to go through some guilt sometimes. Figuring out where each client needs a different kind of support from me keeps it interesting and fulfilling. I love unpacking that with people and giving them a safe space. I'm not afraid of people's emotional response because I have that background.”
Convinced even before the free consultation, I signed on to a Style Shift workshop. This remote (Kinney lives in Austin) several-week program packed with video chats, strategizing and shopping support would take me from a shopping-phobic, rattily-dressed slouch to — hopefully! — a savvy, confident, dresser. Spoiler alert: It totally did — but not without some growing pains.
Step 1: Go deep
Week one brought lots of homework. Rather than plunging into shopping, or even purging my closet, I first needed to step back and think about my style challenges, what my style says about me (and what I want it to say), and then some deeper reflection: Where am I in life? What are my values? When have I felt my best and when did I last feel amazing in my clothes? The questionnaire called for brutal honesty, assessing things like, “what do you think people think when they look at you?” (You mean in my ill-fitting jeans, stained hoodie, tattered shoes and grubby dog-walking coat? I don't even want to know!) The anonymity of answering the thought-provoking question by email made it easier. It felt more like unloading on a therapist than talking with a stylist.
Get the better newsletter.
That's intentional. “Right off the bat I need clients to trust me in order for the process to work,” Kinney says, “so I really open the door for that communication. If I'm not being told all the things going on there's no way I can support someone through that process.”
In between the heavy stuff was something more fun — Pinterest time! I created a board just for the two of us where I pinned everything that spoke to me. Without stopping to second-guess if a piece of clothing was “me,” without ruling things out because of cost, I just pinned my little heart out. Going back to scroll through it, it was easy to see patterns appear. I like stripes. A lot. And a vintage flair. A kernel of what I want my style to say began to materialize.
Step 2: Closet time
Next up was a deep dive into my closet to identify the pieces I wear the most and those I love the most, and what each evokes in me and says about me. Looking at so many ill-advised choices, and items I'd wear for lack of anything better, was discouraging. I had to remind myself this was the slog before the good part. I also wasn't alone.
So many people get stuck when it comes to their wardrobe, Kinney says. They hate shopping, “or don't know how to shop in a way that gives them results they want.” Part of a stylist's job is developing a strategy, she explains. We need a strategy for shopping? Think about it, Kinney says. “How many things have you bought that sit there that you've worn once? A lot of times people waste money buying the wrong things and with a strategy you can make easier, time-efficient decisions and save money.”
Step 3: Bring me a glass of wine?
After our second video call, it was time for the heavy lifting. This is where I literally took every single thing out of my closet and sorted into piles. We had Love, Love but, Meh, and donating or selling. The mantra here? “Be ruthless!”
Although I'd have said there was almost nothing in my wardrobe I loved, it was surprisingly difficult to discard things. This is where it became clear how emotionally attached we can become to our clothes.
What I needed to remember, my mentor reminded me, is it's not about the article of clothing. As much as I treasure the memory of buying those jeans at the thrift shop in Paris and wearing them on that wonderful trip, I don't have to keep the jeans – which are uncomfortable and don't fit well — to keep the memory. And yes, that powerlifting hoodie speaks to who I was at a transformational time of my life. But the oversized hoodie is not a talisman; I don't need it to remind me of the accomplishments that meant so much to me. As a deeply nostalgic person this was the hardest part of this process.
Many clients struggle here, Kinney says. “It's a lot of baggage in there,” she notes, “and everything is attached to an event, or a memory, or even an emotional state of mind you were in when you purchased it, or you remember someone giving you a compliment. A lot of times our feelings have nothing to do with the clothes but the memory around the clothes, their significance, and not even whether it looks good.”
“I try to help people separate and objectify their clothes,” she goes on. “People are hiring me to help them make those decisions … Inserting the objective role into something subjective is where my sweet spot is in the closet sort.”