I Mastered Effortless Style Once I Embraced the Effort

Look at Instagram and you’d think everyone woke up perfectly imperfect. Fashion, beauty, social media, pop culture, all cultivate a myth of effortlessness. In this package, ELLE.com acknowledges, dissects, and celebrates the effort. Because effortlessness is a privilege that not everyone can afford. And there’s no shame in admitting you actually love putting in the work.

A cropped black jacket with dramatically belled sleeves, a black silk camisole, years-old high-waisted creased-front black dress pants, re-soled black patent leather maryjanes, and a long-pined-for, finally-purchased, gold and blue enamel necklace with an “A” charm on it for my then-3 ½ month old daughter Ada. That’s the outfit I wore on my first day back to work after maternity leave. I thought about it. I tried it on the night before along with a few other options. I texted photos to my core fashion-vetting friends for their approval. I wanted to do everything I could to set myself up for success that day—to re-enter the world of “just following up!” emails and urgent deadlines and meetings and ideas and words and Twitter—and I knew that feeling good in my clothes would help make that first day back successful.

The outfit worked. I felt pulled together and excited to dive back into the challenges of this job. I took the compliments that came my way that day. And in the following days and months, I’ve put more effort into getting dressed than ever before; I’ve never tried harder to put together outfits, and I’ve never felt better about myself in them.

Stepping out of my apartment in a well-planned work outfit didn’t always bring me joy. Actually, it used to make me anxious. I remember many occasions where I left my apartment only to immediately regret the outfit I’d put on. I spent the first few years I worked in fashion feeling, to varying degrees, self-conscious about how hard I was trying. Any efforts to level up my basic professional wardrobe seemed only to highlight my insecurities. I used to go to sample sales and buy something just because it was on sale, only to have it hang in my closet for years unworn. I would buy clothes for “occasions” like New Year’s Eve (a “going out top” from H&M) and then wear it once and never again. I was still figuring it out. I worked in an industry where self-presentation seemed to matter a lot, and in my mid-20s, I was racked with self-doubt and bewildered by my peers who seemed to have it all figured out—and financed.

All this is to say that I’ve always put effort into getting dressed. Now, I just enjoy it more.

What changed? For one thing, I got lots of practice figuring out what I like, and what suits me. For another thing, I got older. I care less what other people think of me or if they can tell how hard I’m trying. I also became a mom. Now, getting dressed for work is cultivating an identity that is just mine—it has nothing to do with that other all-consuming part of my life.

I’m still sorting out what I wear when I chase after my now 1-year-old daughter. It’s often sweatpants, a t-shirt, no makeup, and my hair in a very messy, not at all cute, bun. It has to be comfortable and it will get smeared with food. I still haven’t found the right shoes that I can just slip into while holding her (anything with laces or straps or buckles is too tricky). But I know now how to get dressed for work. I’ve figured out what works for me, what makes me look and feel confident, and I relish in picking out outfits and getting dressed up. It’s a sharply tailored blazer (usually from Altuzarra) with jeans and heeled boots; a ruched pencil skirt (I wear the same Preen one I got on final sale over and over again) with a crewneck sweater or a t-shirt (and heels); it’s a printed midi-length dress or a jumpsuit that fits like a glove. I can wear white clothes and fussy clothes and heels and delicate clothes—clothes that I wouldn’t last a second in while momming—clothes that are just for me. I learned from being around lots of stylish women (particularly Samira Nasr and Ruthie Friedlander) and from years of practice: looking that breezily confident takes years of figuring out what you like and caring less about what everyone around you does.

See, there’s this nebulous idea that beauty and style are innate and shouldn’t be worked at. It’s perpetuated by Instagram, to be sure (you did not #wakeuplikethis), but has been around much longer (see: the foundational French New Wave It-girls from the ‘60s and Naomi Klein’s seminal 1990 work, The Beauty Myth). We all know it’s a lie but it’s nice to be reminded. So over the next week or so on ELLE.com we’ll be celebrating the effort, admitting that it’s ok and even fun to try, and taking a closer look at the privilege surrounding the idea of “effortlessness”—who it’s afforded to, and who is left out.