The Effort to Look Effortless
Plus my ode to the button up shirt and how it became my signature style piece to look and feel effortless.
Before COVID, I wore dresses. All the time. I had more than I could count, and bought them from and wore them to my marketing job at a high end women’s retailer in Portland. Then I experienced what I can now identify as burnout, and left my job to focus on my kids and the family wine business. After a six month sabbatical, just as I was getting my resume dialed, COVID happened, and we all stopped getting dressed (among other things). I gained weight and lost it, the world slowly opened back up, and we all started wearing outside clothes again. But said world was much more casual, and the dresses sat in my closet. Then, my dad, who had been ill for a long time, began to decline, and despite returning to work in fashion, I was doing the bare minimum to get dressed. When my dad died, it felt like game over. Enter my Emotional Support Outfit era. Jean shorts and a t-shirt, or jeans and a sweater, depending on the season.
At some point last summer, when I was really starting to come up for air or whatever metaphor makes sense for coming out of a prolonged grief fog, I bought my first really Good Button Up shirt. This wasn’t my first button up shirt; I’ve been wearing button ups since forever, and have considered them a Hero Piece in my wardrobe for years. After all, we Millennials are corporate girlies at (fashion) heart. Who else had the pastel rainbow of 3/4 sleeve button ups from The Gap in the early aughts? Of course, I’ve had my share of button ups from J.Crew and the like - after my failed hipster era of course - and baring my chambray shirt from Madewell that I wore to, literal, shreds, they’ve always been slightly off. A little too slim in the shoulders, with too many darts, or too short in the sleeves. A woman’s shirt, not a man’s shirt cut for a woman.
This Good Button Up sparked something in me. In fact, I included it in the 10 Best Things I Bought in 2024 (my third post and most viewed to date) and I wore it in my (recent and first ever) headshots. For a period it was a key part of my upgraded Emotional Support Outfit. This spring, as work picked up, I needed to throw on more polished pieces than just jeans and a t-shirt to see clients. But after a few months of this formula of button up, jeans, blazer and/or sweater, and loafers; it was no longer an Emotional Support Outfit, it was something better. I wasn’t just getting dressed to survive, I was getting dressed to feel good. Not only was I climbing out of my emotional and style rut, but I was turning this simple silhouette into part of my style identity.
I’ve dubbed this new formula, the level or two above an ESO, the Effortless Outfit. It’s the look you grab when you already feel good, but maybe you just don’t have the time or energy to start from scratch. The pieces you can put on that feel and look like you, and you don’t just feel okay in them, you feel fucking great. The Effortless Outfit won’t come to fruition over night, it will take time and effort to identify and fine tune. And, like mine, it may evolve from your ESO.
I know this all sounds really similar to my parameters for an Emotional Support Outfit, but if you’ve struggled with anxiety, grief, depression, or just an excessively stressful period of time, you know how it feels when you just can’t. And that is what the Emotional Support Outfit is for. It is comfort and protection, the outward projection of being okay, when you’re wrecked on the inside. We all need a little comfort and protection from time to time.
I’ve since gone a little crazy with the button ups, but if I’m not wearing a white t-shirt, I’m probably wearing a button up. And I’m just not wearing dresses as often as I used to, though I still identify as a Dress Person™. I’ve acquired a few (ahem five-ish) more Good Button Ups; white, black, off-white (similar), mix and match stripes (similar), and black and white stripes (similar), to name a few.
Ed. Note: this isn’t so much a How to Style a Shirt post - and both wrote excellent and extensive posts on the subject that you can read here and here, respectively. Consider this a brief reflection on what the Good Button Up means to me, my personal style, and what it means to look and feel effortless.
The best part of a button up rather than a t-shirt? It can be the outfit. Don’t get me wrong, when the weather is cold, it’s very much the base layer, but in the warmer months, it’s the stand alone, star of the show. It can do most of the talking with minimal effort; with pulled up sleeves or the cuffs worn long and loose, collar popped and crisp or relaxed and a little off kilter, barely buttoned or tucked and tidy. It even functions as the third piece à la
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I’ve had friends and clients say they were channeling me when reaching for their button up in recent months, and I feel seen and flattered all at once. If my go-to, idiot proof, Effortless Outfit can inspire someone to get dressed? Then all the effort and, let’s be real, stress to find that formula feels worth it.
Effortless seems to be a buzzy word amongst the fashion crowd. We all want to look -or more importantly, feel - like the, seemingly, effortlessly stylish girls we see on Instagram, TikTok, and here on Substack. But I want to debunk the myth that anyone is effortlessly stylish. They may have an innate sense or appreciation of style, but most likely it started with an interest in fashion (or art, or design, or literature, or film, or any of the other things that influence people’s taste) and they leaned into it. They studied, shopped, curated, and collected a wardrobe full of items that look and feel like them, therefore making them look and feel effortless. A lot of effort went into developing that sense of style that appears so effortless from the outside. As Mike Birbiglia (so charming, who knew?) said on Las Cultch, “Literally everyone good at anything tries hard.”
Sure, I’m probably being influenced by the current trend cycle - key word here is effortless - and was probably already wearing more of my relaxed yet tailored pieces before expanding my shirt collection and steering clear of the more delicate, feminine pieces in my closet. But I’ve been preppy-ish, essentially since birth, so I’m not veering too far off the path. And as an avid collector, and someone who’s old enough (oof) to rely on hindsight, I’m not getting rid of all those dresses I wore so much BC, I’m just saving them for later.
Have you seen the photos of Charlie XCX’s wedding to George Daniel? She looked so happy and so CHARLIE in her sunglasses and Vivienne Westwood mini dress. I was also really taken by the flowers, and did a deep dive on her florist and internet sweetheart, Hamish Powell. He’s a must follow on your app of choice (Instagram or TikTok, pick your poison).
As a certified Cat Person, I can’t stop thinking about this charm from Catbird, and promptly sent it and this TikTok to my sister.
After a visit to the pediatric orthopedist (it’s a sprain, if not a break?) my freshly booted 11 year old and I went to Costco to renew my long lapsed membership. We - very slowly - browsed the aisles, while my child experienced the joys of a Costco sample, and managed to spend $150 on about seven items.
With our renovation winding down - as of publication we passed final inspection and we move on Wednesday - I’m shopping for the small, functional, and essential things. I found these towels - a Tekla dupe if I may say - for the primary bathroom, and these for the boys bathroom. After two classic and maybe, just a little boring, bathroom renovations, I went BOLD and the striped towels are the cherries on top.
How do you feel about the word effortless? Since when is it a bad thing to try (or look like your did), i.e. put in effort? Tell me your thoughts in the comments.
Thank you, as always for reading, and for being here.
Talk soon,
Fanny
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Definitely agree with your and the other comments a la - what is the problem with putting in effort? I think some of it is the idea that women should be “effortless” in their perfection. But lately, I also often feel like “effortless” is code for white and/ or thin. Your post is fantastic, and I appreciate you breaking it down. For me, your looks appear more simple and straightforward, tight color palette - all of which takes some effort! But I regularly see looks that are, say, a cropped white tee and cargo shorts (or similar), or high waisted pants and a tank top- the models/ influencers may look fantastic in them, but it is because they are very very thin, and likely white, and our eyes are trained to see both of those things as “effortless” and “perfection”.
I always tell my kiddos it’s OK to try- it shows you CARE! And same applies to getting dressed. We should look like we have put effort into our looks- and I love how you make it look so easy!