Is It Possible to Wear a Hat to the Office Without Feeling Completely Extra?

My aesthetic is made up of two warring personas—one creative, one practical.

Creative Lindsey spends a lot of time shopping online, dreaming of the incredible outfits she’ll concoct and the Instagrams she’ll inevitably take in them. Practical Lindsey offers a dose of reality; she prioritizes sleeping over the time-intensive process of getting ready every morning, and resents the notion of posing over and over (and over) again for the sake of an ephemeral social media post.

The result is something of a compromise. Some days I wear makeup, some days I don’t. I usually try to do something with my hair—either washing it so that it falls into a nice wave, or braiding it when it doesn’t cooperate. And my outfits tend to be fashion-forward enough to demonstrate care, but not so fashion-forward that they’d warrant the attention of a street-style photographer.

In other words, there’s some kind of middle ground in this dichotomy, and I manage to find it. Except when it comes to hats.

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Hats are, for lack of a better term, a mood. When you wear a hat, you’re telling the world: I put effort into this outfit, and I know I look fucking great. Hats project thought, care, intention and confidence all at once. And the kind of person who wears a hat is (almost always) the kind of person who manages to wake up early and assemble a thoughtfully curated ensemble every single day.

I am not a hat person. In fact, my entire aesthetic runs counter to what hats represent—well, the practical half of it does. The creative half loves hats. She dreams of wearing them—to the park, to parties, to the office. She even owns a few.

And this week, I indulged her. Much to the chagrin of my rational half, I challenged myself to wear a hat to the office. And to do it again and again and again—until I’d exhausted the four hats I had in my possession. My inner cynic told me I’d feel extra—maybe even embarrassed. Who did I think I was, anyway?

But I did it. And I documented every single day of my brief sartorial journey.

Day 1: Baker Boy Cap

The baker boy cap has emerged from the aughts (or wherever else it came from) to become one of 2018’s trendiest pieces. I’d never considered the accessory until Lack of Color kindly sent one my way (Riviera Cap, $99 at Lack of Color), and I immediately set to work on styling it.

The cap seemed like it’d complement an updo—which always looks better with drop earrings, which always pair well with straight necklines. So I threw together a black sweater, gold earrings and some wide-leg jeans. The volume in the jeans balanced out the volume of the hat (great, since they’re rendered in similar colorways).

The final product was a look that felt retro and contemporary at the same time, and I had a surprising amount of fun wearing it.

When I first got to the office, my desk-mate complimented me on the hat. I immediately replied, “Do you think it looks too extra? Like, who’s that bitch?” Her response: “I think it looks extra, but in a good way. Like, who’s that bitch? Not who’s that bitch?”

At the start of the day, I told myself I’d leave my hat at work. But by the end of the day, I was contemplating commuting home in it. I wanted my friends to see the fun look I’d assembled—the one that had garnered compliments from several coworkers and even a couple strangers.

Any hesitance I’d experienced at the outset had been replaced, at least temporarily, by a little care-free fun. And I headed into Day 2 with a much less reluctant spirit.

Day 2: Black Cowboy Hat

Day 1 was undoubtedly extra, but Day 2 was even more so. I spent an hour trying to figure out how to style another black hat I’d received for free—specifically, one from Carve Designs (Capistrano crushable hat, $38 at Carve Designs).

Since it was a cowboy hat, I figured it’d be easier to wear than the baker boy cap. Wrong. It was much more voluminous, and required some serious finessing. (Dressing like a cowgirl is a look, but not one I felt like sporting.)

After a few iterations, I landed on the following combo: a chartreuse chenille sweater, black jeans, black boots and a multi-colored silk scarf—tied like a bolo tie. The outfit definitely felt Western-inspired, but the palette kept it from skewing too literal.

The first thing I heard when I walked into the office? “Lindsey, I love your outfit!” I expressed concern: “Is it working? I’m not sure about it.” (Specifically, I was concerned about the color scheme feeling very spring.) “I think it looks super fall,” my coworker responded. And that was, honestly, enough to get me through Day 2.

I met a friend for dinner after work, and wore my hat to meet her—partially because I had hat hair, but mostly because I knew the outfit wouldn’t work without it. I was no longer just a girl who wore hats to the office; I was a girl who wore hats everywhere she went. (For what it’s worth, my friend showed up wearing a beret, so I was in good company.)

Day 3: Bucket Hats

Bucket hats might be a summer staple, but they work just as well during fall and winter. (OK, I wasn’t entirely convinced of this. But a burgundy chenille bucket hat I’d received from Marshalls (only available in stores) persuaded me it had to be true. I mean, who wears burgundy chenille when it’s hot out?)

The first time I tried to style this hat, I failed miserably. I attempted to wear it with a black sweater and red plaid midi, but the look skewed very Paddington Bear very fast.

I traded my ensemble for an animal-print button-down (that matched the bucket hat’s color) and a chenille sweater (that matched the bucket hat’s fabric). I topped off my look with black Chelsea boots, which paired incredibly well with the hat; I was giving off Singing in the Rain vibes, but definitely making it fashion.

By this point, I was a hat aficionado. When my desk-mate offered her daily hat compliment, I replied: “I’m not sure about the bucket hat, but I think I’m making it work.” (Small steps, people.) She assured me I was making it work, and I went about my day without giving much thought to the hat.

Day 4: Vintage Cowboy Hat

Indiana Jones is a woman, and her name is Lindsey Lanquist. By this point, I’d become such a skilled hat stylist that I assembled my entire outfit before picking up this hat from my friend, who’d scored it for a mere $8 at a thrift store.

The ensemble I threw together resembled something I’d wear on the daily: an animal-print midi dress, a black pullover sweater, some black ankle boots and a pair of drop earrings.

I was glad to have crafted a hat outfit that felt distinctly me; the first two were incredibly extra, the third was a little extra—but this one felt  more authentic. The hat definitely took it from low-maintenance vintage to over-the-top vintage, but it spoke to my dissonant aesthetics in a way the other three didn’t manage to.

A few times throughout the day, I took off my hat—trading it for a haphazard updo. This had less to do with some deep-seated insecurity and more to do with the fact that hats can get very hot and very uncomfortable. (You deserve to know the truth.)

But when I headed to grad school that night, I wore the hat. Because it was warm and I liked it and I’d finally overcome my hat aversion—well, mostly.

Final Thoughts

Like I said at the beginning of this piece, hats project thought, care, intention and confidence all at once. They also project vulnerability.

When wearing something so eye-catching, you can’t hide—you sacrifice any plausible deniability or semblance of nonchalance you might otherwise cling to. Because you’re announcing to the world that you care. That you’re trying to look good. That you put forth effort to do something interesting—and if it fails, that’s on you.

This story offered me a way to mitigate that spotlight effect. Any time someone mentioned my hat, I laughed—and brought up my article. “Oh, I don’t usually wear hats either. I just have to do this for a piece.” The speed at which those words entered my brain—and exited my mouth—caught me off-guard; my mind had an excuse at the ready just in case anything went wrong.

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The good news? No one else sees that spotlight you feel beaming down on you every day. No one gives a fuck about your hat. The lens you’re using to analyze your outfit—or yourself—is far more critical than the one anyone else greets you with.

As far as they’re concerned, you’re not that bitch, you’re that bitch. The one who was bold enough to wear a hat to work. You might seem extra, sure. But a delightful kind of extra—a fun kind, an exciting kind. I received more compliments on my outfits this week than I have in my entire time at StyleCaster. One of my coworkers even told me I was convincing her to give hats a chance. That’s a good feeling.

So is it possible to wear a hat to the office without feeling completely extra? 

Short answer: Not really.

Long answer: Not really, but you’re the only one who’ll feel awkward about it. And you’ll probably get some seriously great mirror selfies in the process.

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