The Beautiful Freedom of Wearing the Same Thing Every Day

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I was starting to short-circuit, so I frantically emailed Alison, whose wardrobe and sense of personal style are a constant inspiration.

"I wear the same thing to every meeting: a v-neck t-shirt, a blazer with the sleeves rolled up, fancy flats, nice jeans, funky-ish jewelry," she wrote. "Having an uniform makes me focus on the meeting and not what I'm wearing."

Uniform dressing is certainly not a new concept. But as the business world grows more relaxed, it can be easy to lose sense of what's appropriate. You can wear jeans to the opera, white after Labor Day, a t-shirt to your cool startup job. Overalls are back in, sort of, as are Adidas slip-ons, fleece vests, and baggy jeans. Any of these could be be appropriate for the right type of meeting, interview, or breakfast, as long as you worked it.

This unprecedented sartorial freedom can feel more stressful than liberating. You want to look stylish, and cool, and professional, and hireable, and also, like, fun to talk to at meetings. Deciding what to wear, more than ever before, is branding. And nothing is more important than branding.

It's no wonder Obama (and, more recently, Mark Zuckerberg) has a famously regimented approach to dressing. "You'll see I wear only grey or blue suits," the president told Vanity Fair in 2012. "I'm trying to pare down decisions. I don't want to make decisions about what I'm eating or wearing. Because I have too many other decisions to make."

While my meetings in LA certainly wouldn't require me to answer the types of questions President Obama faces on any given day ("Do I want a water bottle?"), I am easily frazzled enough to find the idea of one general outfit appealing. So I decided to follow Alison's advice.

Before even saying a word at these meetings, I knew I wanted my clothing to project three qualities: 1) Put-together. 2) Cool. 3) From New York.

Put-together is probably the top attribute I seek to achieve while getting dressed, and also, for me, the hardest. It means looking deliberate and wrinkle-free, where every item of clothing works in harmony with the rest of the outfit. (Or in layman's terms, all black.)

"Cool" can be translated roughly to mean "someone who leaves the apartment and socializes with human beings a normal amount." Someone you wouldn't mind being stuck on a conference call with while waiting for the other people to dial in.

And "from New York" is how I wanted to distinguish myself from the sunny, post-Coachella vibe of everyone else in California. I'm from New York, I go to the theater, I live in a walk-up. (Once again, all black.)

To shop for my uniform, I enlisted another guru-friend, Julie, and headed to Comptoir des Cotonniers, a store which seems hopelessly sophisticated to me—but which I'm pretty sure is actually equivalent to The Gap in actual France. Comptoir is a store I generally only browse during a (significant) sale, or in rare moments when I'm feeling particularly flush. But as my dad wisely said, "If you were a law student interviewing for a firm, you would definitely invest in a suit, wouldn't you?" I guess? I'm not a law student. But if leaning in means shopping, then so be it!

Early on I found a black short-sleeved sweater with a crisp white collar attached to it (exactly the kind of shirt that a more capable, stylish girl could create for herself by literally wearing a black sweater over a white collared shirt, Julie pointed out), which I planned to wear with black skinny jeans. Because wearing the exact same thing every day for three weeks is insane, I also bought a grey-ish dress that was described to me as "sporty élégant," and which I've since seen exact replicas of at both J.Crew and Madewell for about $100 less.

And finally, the coup de grace: a pair of leather lace-up boots in Oxblood, to go with both outfits. More expensive than the dress and shirt, combined.

Altogether, the total came to a good portion of a month's rent. A pretty hefty price-tag to looking put-together, cool, and like I'm from New York. (Dressing above your means is part of looking like you're from NYC, right?)

I felt a little panicky after spending so much money. I could have gotten a wardrobe at Zara for what I spent on one outfit (okay, two outfits). Julie patiently led me around Soho while I did some breathing exercises and tried to validate my choices. Why did I feel like I had to look a certain way for my career? Men certainly don't feel this pressure. Menswear is already practically a uniform (shirt plus pants, repeat), and I know that my male counterparts don't worry much about looking cool, or put-together, or fun, or any other adjective. Why should they? Guys in my industry are taken seriously regardless of what they wear. But women have to bolster their creative output with aesthetics. It's like we feel the need to say, on some subliminal level, You like my outfit, so you can trust me. You approve of how I look, so you might like my work, too.

When I went to Los Angeles, wearing one of two things every single day did, in fact, make my visit transformatively easier. To get up and just put on clothes reduces the act of wearing clothes to its most utilitarian aspect, something I haven't felt since my days of wearing a school uniform (which, for the record, I RAILED against.)

I liked what I was wearing every single day, and I liked knowing my look was consistent. I got comments and compliments, enough to make me feel confident in my outfit choice, but never so much as to pull focus from the topic of the actual meeting.

I'm glad I put a lot of thought, and time, and money, into deciding what to wear on that trip. Because after that, for whole three weeks, I experienced the freedom of not having to think about what I was wearing at all.