Every Winter, my friend Amanda and I spend a long weekend in New York City. It began almost a decade ago, when I was post-breakup and ready to reclaim a missing sense of myself. New York had been at the center of that relationship, and I wanted to take back the meaning of it and recreate a version that belonged to me.
Years later, those trips continue to wake something up in me. A sense of possibility permeates the air. New York’s potent vibrancy provides the background, but it’s also the alchemy of multiple days with a longtime friend. The shared history of language and jokes, covering hundreds of city blocks and conversational topics, tucking into booths and sliding into bar stools in front of crisp beers and salty snacks. The fizz of discovery. The exhale of familiarity. The trip is an anchor. It reminds me quality time with old friends is both a salve and a spark. They know who you’ve been, who you are, and who you could still be. They hold up a mirror to the selves you might have forgotten about.
This trip also brings a new energy to the act of getting dressed. I take chances I don’t take back home; I question less. The external noise in my head softens. Which is not about being someone new, necessarily, but about revealing what was already there.
Items and ideas laying dormant in my closet and brain finally make their debut. The outfits aren’t groundbreaking, but they are undeniably mine. They make my inner self and outer self feel in sync. I walk with more confidence. I take pictures of them without hiding my face. The endless second guessing recedes, and in its place arrives permission.
Over the last year, I realized I’d been denying the joy personal style brings me. I’d been diminishing it. After years of working from home, I deeply missed wearing outfits. The ones stamped with personal identity. Looks that gave me that missing puzzle piece feeling.
Because I wasn’t regularly going into an office, my clothes became form over function. Days I got dressed for meetings, I’d change mindlessly back into old sweats shortly after. Over time, the energy of these choices filtered into my days. It brought a lower hum to them. And as a result, part of my inner light dimmed.
I know I’m not alone in experiencing a changing relationship with my closet. If the internet is any indicator, there are countless people looking to rediscover (or find) their personal style. And while I love style content, I look at photos of me as an adolescent, with her high tops and bangs and patterned tights and white turtlenecks, and I think: oh—that’s still me. I still wear all those things, even if their form has evolved. I actually knew what my personal style was, at its core. I’ve known for years. I had just been putting it on mute.
There’s a telltale signal for me that I’m internally ignoring something. I begin looking for advice and input from every possible source but my own. I did it a lot over the last year or so. Things got harder in various ways (in both the world and my life), and I attempted to to-do list or advice my way out of them. Don’t get me wrong: a plan holds its own power. I love me a plan. But I was making a crucial mistake: believing my inner voice and needs didn’t hold equal or more weight than external advice. Within that frame of mind, there was no room for the small joys my inner voice was calling for. We had shit to do, and it needed to quiet down.
Of course, this went beyond getting dressed. It applied to everything. Feeling better wasn’t about finding the perfect guidance or formula and suddenly being set. It was remembering my individual autonomy. The advice and input helped, but the un-locker was giving me space to then decide what worked for me. To honor and act upon the privilege of being an architect of one’s own life. (Kathleen Smith writes wonderfully about this concept in her two books, which I’ll be reviewing in my next post).
Over the last months, I’ve made small energetic shifts across my days. Getting dressed became an act in which I prioritized joy. As a first step, I removed and temporarily hid anything from my closet that felt “meh” to me (even if it was on trend), trusting I could bring it back if I missed it.
I wore what I was drawn to, regardless of plans, trusting I could style it accordingly. I took pictures and noted when something didn’t feel right, trusting I could adjust.
I began relearning what I loved. I rebuilt a sense of personal faith in small decisions. Every outfit wasn’t perfect. But each one, combined with displays of inner trust across other areas of my life, was a small step in returning to myself.
***
Last month, over noodles at a Ravenswood Cuban/Filipino diner, a close friend asked us for our personal do’s and don’ts in 2025. The answers were threads in the fabric of a life, daily joys amounting to long-term meaning. Savory breakfasts. Diverse forms of movement. Time spent in nature. When it came to me, I thought of the girl marching down her eighth grade hallway in crimson Chuck Taylors, feeling alive and powerful and awake to the world. I didn’t hesitate. “I won’t reject my interests.”
“Wow,” my friend said. “That was so confident.”
I nodded. Inside of me, something shifted. It was small, but the foundation was strong enough to build upon. Day by day, it was plenty.
Relevant Reading:
Erika’s Closet Clean Out Guide (Love how she suggests an intention when cleaning your closet—what energy do you want to feel when you open it?)
Kate’s Personal Style Essay (I love Kate’s perspective on identity and self-trust, and this essay beautifully captures both.)
Morenike’s Wardrobe Relationship POV (The power of getting to know yourself and your preferences in any area, beautifully applied to one’s closet).
Amy’s Knowing Herself List (Love this idea—my friend Julia had a list of things that made her happy on her wall when we lived together and it was such a self-honoring thing to display).
These outfits are undeniably you!!! I adore each and every one. Your style has always been incredible, and I’m so glad you’ve reawakened your passion for fashion and dressing for YOU. This post may inspire me to do the same…as I sit here in joggers and Taysom’s school sweatshirt. Love you xo
Loved seeing your face and Amanda’s at the top of my Substack feed! 😍😍
What a beautiful post, Brooke. 🥰 I can relate to this so hard. When I look back at pictures from childhood, I’m always wearing something funky (and generally three outfits a day)—it’s how I expressed myself.
I have cut back on buying clothes over the past five years due to budget. I had been doing Nuuly for a while and canceled it to save money. But I’ve been feeling like that spark of joy and creativity in my life is gone. (Even if it’s clothing I picked out through a subscription service.) I wear sweatpants and “a cute top” which is usually an old sweater these days and it’s sucking the life out of me. You’re motivating me to figure out how to dress up for joy again!