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Overcoming Casual Creep: Upgrading My Work Wardrobe Without Losing Myself

May 24, 2018 | Filed in: Your Closet

Ever have those days where getting dressed for work feels like an insurmountable task? You’re not alone. In celebration of our creative-casual summer collection, A Certain Ease, here’s how one MM team member learned to up her workwear game—without sacrificing comfort.

Years ago, with the over-confidence that comes with being very young and having had a little too much wine, I once declared that I would never take a job that required me to wear a suit. In college, I had gleefully embraced the practice of wearing sweatpants (or worse) to class, and I did not view entering the workforce as a good reason to compromise on my comfort level. Lucky for me, my career ended up being in advertising and marketing, increasingly casual industries. Gone are the days of gray-suited ad men and glamorously made-up women roaming agency hallways—although those ’60s silhouettes did look great. These days, you are more likely to spot advertising professionals chasing the latest sneaker trend than you are to catch them in cocktail wear. However, as I occupied several workplaces over the years (each one boasting a “casual” dress code), I began to experience a peculiar phenomenon when it came to getting dressed for work. I’ll call this affliction “casual creep.”

Casual creep is what happens when you take a job at an office with an informal dress code, and then watch your standards slide from the apex of workwear chic (in my case, that was usually my interview outfit) to the lowest permissible level (for me, this was jeans and an old T-shirt, thrown on five minutes before leaving my apartment, no makeup, and messy hair in a bun). On occasions that called for more formality, I pulled it together. But left to my own devices, I couldn’t help myself—absent strict guidelines, I slid ever deeper into the throes of casual creep. The only indulgence I wouldn’t allow myself was wearing workout gear to the office, because I’m not a monster—though the thought crossed my mind more than once.

This reached its nadir at a job where I had a co-worker who was also a neighbor. After spotting me properly dolled up en route to a party one Saturday, he later remarked to another colleague: “Sarah… looks different on weekends.”

The shame!

Back then, I hadn’t fully realized how much my work could be impacted by how I dressed. I am not an inherently formal person—my favorite item of clothing to shop for is pajamas, I do not take pleasure in styling my hair or applying makeup, and I have always prized my ability to get ready quickly. After all, I have #betterthingstodo, right?

Well, after “Sarah looks different on weekends”-gate, I changed my tune. If my coworker notices my casual creep this much, I thought, what about my boss? What else was my level of dress saying about how I felt about my work? I needed to find a way to dress for the office that was relaxed and easily pulled-together, but that also communicated how I wanted to be seen at work: professional, enthusiastic, and someone whose taste you could trust. Over the next few years, I made progress, but I still couldn’t shake the association of “work clothes” with discomfort, huge dry cleaning bills, and not feeling like myself.

Enter MM.LaFleur: In joining the team here, I have discovered that there is a whole professional spectrum in between “jeans and an old T-shirt” and “a full suit“—one that allows me to stay true to my inner sweatshirt-loving dirtbag. Here’s how I’ve learned to resist casual creep, while still feeling comfortable at work.

1. Elevate your basics.

comfortable casual work clothes

The Didion top in etched herringbone and the Oshima pant in black are grown-up versions of jeans and a T-shirt.

It’s embarrassing that I am just learning this now, but a well-fitting black pant and a top with a T-shirt silhouette in silk instead of wrinkled cotton can be just as comfortable as my former go-to uniform. I threw a leather jacket over this ensemble, which is quite fancy by my standards, but the Didion and Oshima stand on their own—they’re comfortable, chic, and make me look like an adult.

2. Go halvsies.

comfortable casual work clothes

The Lenox skirt in rosette elevates even the plainest of tops.

If you really can’t bear to part with your T-shirts, pair one with a more formal piece (like I did here with the Lenox skirt). It makes the casual top feel like a much more intentional, stylish choice, as opposed to the only clean shirt you could find in your drawer. The lesson here: If you must go casual on the top or bottom, balance it out with a more formal piece.

3. Get sneakier about comfort.

comfortable casual work clothes

The Gwen dress in charcoal can do double duty as cocktail attire or a so-comfy-you’ll-think-it’s-pajamas daytime piece.

Once you’ve known the luxury of wearing sneakers to work, it’s hard to give that up. To compromise, I’ve started wearing mine with more formal dresses and tops—a luxurious knit like the Gwen dress has a way of making everything I’m wearing feel more polished. Also, the comfort level offered by a high-quality knit cannot be overstated.

Though I still have days when I look a bit worse for wear (braving the New York City subway every morning will do that to you), these guidelines have helped me raise the baseline level of my work wardrobe. I’ll never be the type of person who loves taking an hour to get ready—so clothes that require a lot of fuss, adjusting, or expensive maintenance are never going to work for me. But I’m happy to have discovered a professional (and, above all, comfortable) middle ground—and to be free from the clutches of casual creep.

Photographs by Lindsay Brown.

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Sarah Devlin is the former Director of Content for MM.LaFleur. She's worn many different hats over the course of her career — from writer and web editor, to social media editor and marketing strategist — but her hardest-won title is Kardashian Historian. Read more of Sarah's posts.

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