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Dress Like Somebody’s Watching: A Freelancer Spends 5 Days in Proper Workwear

July 13, 2015

Most people think freelance writers spend the majority of their days in pajamas—and they’re not necessarily wrong. The elastic waistband has long been the hallmark of the at-home worker. But should it be?

We asked freelance writer Brienne Walsh to spend a week dressing for work—really dressing for work—to see what would happen. This is her account. 

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As a freelance writer who’s only obligated to leave the house to walk the dog, it can be tempting to pass the whole day in exercise clothes. But after spending a week in MM.LaFleur, I found that dressing for “the office” increased my productivity in both expected and unexpected ways. Not only did it put me in the mood to sit down at my desk, but it also made it easier to leave it—and a large part of my job as a writer is being immersed in the world around me.


My schedule was quiet on Monday, so I decided to put on the Claudia, a shirtdress that was so comfortable, I could wear it to sleep. I have some steady work that keeps me afloat financially every month, and I usually try to finish it early in the week.

Claudia 1

In the afternoon, I headed into Manhattan to meet my friend Sadie. We’re working on a book together that’s called Things You Can Make in a Blender. It started out as a joke, but it’s turning into something real. We created a list of agenda items, and put some dates on the calendar for upcoming work sessions.

“You’re taking this so seriously!” Sadie noted.

“I know. I’m dressed for business today,” I told her.

Claudia 2

Brienne in the Claudia and Butters in her own fur.


For the past two years, I’ve been working with my literary agent on a manuscript of personal essays. It’s called So This Is Love—a name chosen by my grandmother—and the essays are about getting married. I was pretty sure my agent was going to drop me, because it took four drafts and a lot of emotional emails to finish it. But late on Monday night, she emailed me to say she’s ready to begin sending the book to publishing houses. She just wanted me to make a few small changes—and more specifically, to comb through the finished draft to see if all of the curse words I used for emphasis were really fucking necessary.

Emma 2

Because it was a special day, I put on the Emma. I adore the detailing on the waistline, and moreover, how the design adds curves in places I don’t really have them. I think I look best in jewel tones, so the deep, rich teal color made me feel really pretty.

Emma 1


I had to run some errands on Wednesday morning, so I put on the Didion and a pair of ripped jeans from Topshop. I absolutely love the way slouchy shirts look with skinny jeans. Not to mention that the name is aspirational— what writer doesn’t want to channel Joan Didion?

Didion 1

When I got home, I worked on a pitch. People say you should follow your passions, and my current passion is ClassPass. I’ve noticed that a lot of boutique fitness studios offer weeklong vacations in exotic locations such as Marrakech and Cartagena. I could never afford the vacations by myself, so I thought, “Why not get a magazine to pay me to go on one?” It’s worth a try.


Every month, I write a review for the London-based magazine ArtReview. When I’m reviewing an exhibition, I try to make myself as anonymous as possible —in the art world, that means understated chic. I slipped on the Winfrey top with the Tribeca skirt.

Tribeca 1

It was the perfect combination of sophisticated but not too dressed-up. I wanted the gallerina behind the desk, upon seeing me enter, to think, “Okay, this person looks like she belongs in an art gallery. I won’t be openly hostile.” And it worked. I slipped in and out of the gallery unnoticed and went home to recuperate. Even though I had nothing much to do for the rest of the day besides write a few blog posts, I kept the outfit on because it was so comfortable.


I tend to buy really girly, flouncy clothes, but now that I’m 32, I want my style to be more sleek. I love the Lydia because it has such clean lines, and even though it’s form-fitting, it didn’t make me feel over-exposed.

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I had a quiet day on Friday. I wrote a story about an encounter with a homeless youth I had on the C train the day before—the subway really is a gold mine of inspiration—and posted it on my blog. Then I went out to meet my friend Laura for lunch.

To keep the outfit casual, I wore it with a pair of cheetah-print Keds, which looked great with the cornflower color of the Lydia.

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We talked about how, while on the surface we’re achieving, we still feel like failures all the time because we are constantly getting rejected by editors. Instead of posturing as we might have when we were younger, we were honest with each other, which is one of many reasons I’m so relieved to be in my thirties—that, along with finally knowing how to dress myself.

Claudia 2

Overall, waking up every morning and putting on a nice outfit definitely felt like playing dress up — in a good way. As opposed to feeling like I was a dilettante who occasionally got paid to write something, I actually felt like a “professional writer.” Dressing well made me take myself and my career more seriously, even when my cat Butters was the only one who noticed.

Photos by Frances F. Denny

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Brienne Walsh is a writer, critic, and photographer who has contributed to The New York Times, The Village Voice, Art in America, Interview, and Forbes, among other publications. She is currently working on So This Is Love, a collection of essays about getting married. Read more of Brienne's posts.

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