Welcome to Office Dress Code Makeover, a new series that will evaluate the stringent office dress-code regulations of Man Repeller community members and then offer creative solutions to help them express their style instead of compromising it.


Sam Cohen, 25, and Jessica Joiner, 28, work at an advertising firm in New York as a copy writer and art director respectively. The dress code at their office is extremely lax but employees are still encouraged to “look professional.” The CEO wears athleisure every day. Most people wear various combinations of jeans and sweaters. Nothing is off limits, per se, but it’s also not the type of place where you could walk in wearing a bikini top and raffia skirt.

The Challenge

I asked Sam and Jessica to show up wearing their “typical” work attire, and this is what they arrived in.

Both Sam and Jessica want to have more fun with their office attire. Because the dress code is so open-ended, they find that it’s super easy to fall into a rut that supersedes the desire to mix things up. “We default into wearing basics that lack the flair we both aspire to convey,” Sam told me. “We’d love to find a way to show off our personalities through clothes while still feeling effortless.”

When I asked them to describe their respective personal styles, Sam told me that she really identifies with the marriage of masculine and feminine elements espoused by Copenhagen street style, like a dress paired with sneakers. Jessica, on the other hand, categorized her aesthetic as “urban and easygoing.” They echoed each other in admitting these elements aren’t always evident in what they end up wearing to work every day, though they wished they were. As I listened, my eyes twinkled and I stroked my chin sagely, flushing with the thrill of an office dress code makeover on the horizon. I asked them to come to the Man Repeller offices the following week, preserving my dignity at the last second by saying “see you then!” instead of “be there or be a rhombus.”

The Solution(s)

Makeover #1, a monochrome bonanza.

During our styling session, I wanted to give Sam and Jessica at least two meaty takeaways that could apply across numerous hypothetical outfits going forward. The first was pretty straightforward: reinforcing that monochrome is an instant “formula” for making a polished sartorial statement without exerting too much undue effort because we are all baby sloths in human clothing and sometimes getting dressed in the morning is a task tantamount to quantum physics, truly. To demonstrate this tip, I selected pieces in similar colors for both women–red Eloquii pants and a red Lands’ End sweater for Jessica, and a cream corduroy jacket with matching pants from Mango for Sam. The color coordination instantly cultivated a sense of put-togetherness in both outfits, which is great for a professional setting, but also super fun for the same reason. Like a penguin wearing a bowtie. If that makes sense.

“It’s such a revelation that you can make a suit out of things that aren’t typically a suit,” Jessica commented after changing into her all-red ensemble. And that’s precisely the point–DIYing your own version of a suit will convey the same coordinated vibe but allow you to exercise more creativity.

My second takeaway involved using Sam and Jessica’s personal style descriptions to suggest a plug-and-play work outfit template for both of them that spoke to their aesthetic proclivities while simultaneously bringing something new to the table. Since Sam told me she enjoyed exploring contrast while getting dressed, and wants to experiment more within the bounds of work-appropriate attire, I styled her in a jumpsuit with a camel sweater underneath, a blazer, and sneakers. The casualness of the jumpsuit and sneakers is offset by the preppy conservatism of the sweater and blazer combo, resulting in an outfit that is equal parts professional and interesting (IF I DO SAY SO MYSELF!!!!!!!)

When Jessica described her style as urban and easygoing, the first thing that came to mind was a Canadian tuxedo, but I wanted to give it a slightly unexpected twist, so I styled her in a dress instead of denim pants and layered it with a white turtleneck and resisted the urge to mime sprinkling salt on the resulting outfit à la Salt Bae. I mentioned this same template could expand into multiple different silhouettes (a denim shirt, a denim skirt, overalls, etc.) but recommended sticking with dark denim and finished edges so as to lean into the more refined iterations of what is an innately relaxed material, as they say in the office dress code makeover biz.

I checked in with both women a few days after our styling brouhaha to see how they were feeling, and ask if the experience had impacted the way they were thinking about getting dressed in the morning before work. Sam told me that she could easily see herself wearing either outfit to the office and that it was helpful to see a tangible demonstration of presentability and creativity coexisting in the same look.

Jessica chimed in, “After our session I totally stepped my game up the rest of the week and started pairing things in my closet in different ways. I have so many new outfit ideas. It also just reinforced how different my energy feels when I actually put effort into a look. There have been times when I put something on and thought, this looks like I’m doing too much. Especially in a more relaxed work environment. But whatever, if doing too much makes me feel good, then I’m going to do too much. And honestly, is looking good and feeling good really doing too much?”

To that question, let me just say: absofruitly never.

Have a friend, or a friend of a friend, or an “asking for a friend” you’d like to nominate for Office Dress Code Makeover? Slip into our DMs!

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