How Do I Dress Like a Boss?

I was recently promoted at an artistic nonprofit. Though people in senior positions dress a bit more formally, I’ve slid into leggings a...



Congratulations on your promotion! The good news is you are not alone in having to figure out how to communicate the new you upon a return to the office. Thanks to a year of remote work, many of us are in the same boat. Your situation just happens to be more official than most.

The first thing to consider is what you want to convey in your new position; what subconscious levers you are trying to push. Generally, if the idea is to communicate authority and confidence as well as creativity (qualities that make your team feel secure in your leadership), the single most important message in any item of dress, whether it’s leggings or a trouser suit, is mindfulness. That means no wrinkles, dangly threads, moth holes or stains, and no clothes that require constant fiddling and adjustment.

But that does not mean clothes with no personality.

The other good news is that any past allegiance to the idea that a more senior job necessarily means dressing in a more “serious” or besuited way has increasingly lost its cred. Women like Marissa Mayer and Mellody Hobson, with their clear love of fashion and femininity and their whip-smart minds, have pretty much put an end to that shibboleth. And after a year in sweatpants, almost anything qualifies as dressing up, which means your options are wide open.

To that end, rather than “dress for the job you want,” you should “dress like the person you admire.” And when it comes to trailblazers in your field, you may think, for example, of Thelma Golden, the director of the Studio Museum in Harlem, who has a singular and striking personal style. Though she almost entirely wears pieces by her husband, the designer Duro Olowu, and his work would be out of reach for many, you can take a cue from the way his designs mix prints and colors all within simple, easy silhouettes.

Then, rather than think about a wholesale wardrobe reinvention, think about a few key pieces you can incorporate into your existing wardrobe. Add a patterned wrap dress, like this one from & Other Stories or a shirtdress like this one from Cos, either of which you could wear on its own or layer atop leggings or pants. Choose a graphic jacket like this D’Iyanu number, which can provide a striking accent, or play with clashing stripes, as in this shirt from Alex Mill. And consider the jumpsuit, which combines tailoring and comfort for days when you are doing some actual heavy lifting.

After all, there’s a lot that can be done within a very basic canvas.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.



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