Reader Maddie sent me this request:
Something I think a lot about is how to balance “dressing for situations that require ‘appropriateness'” vs “dressing in a way that makes me feel awesome and cool.” Like you I’ve been trending much more edgy – cool recently, and it’s a balancing act to figure out how far to let that go when I’m on site with a customer at a big health system. For example, I’m not taking out my eight ear piercings, no sir, but should I balance that out by not wearing my pointy edgy heeled booties? Is a leather pencil skirt too much now that my hair is dyed dark and I’m not pairing it with a cheerful floral, but a dark blouse? (But also, forgive my French, fuck the patriarchy, where does that fit in?) Are there some general ideas/guidelines for how to keep from accidentally going too far? I don’t care too much about offending people, but I do read the boss-lady blogs like Corporette and I really struggle to reconcile the dress-for-you vs dress-for-those-around-you-at-work messages I feel I get from different camps.
SUCH a tough one. And I will open this particular can of worms by saying that learning to balance your personal style preferences against the expectations of those around you is a delicate art, and also a highly individual one. What you can “get away with” depends on your environment, tasks, and – to some extent – personality. I can offer loose guidelines, but you should always trust your gut. And when your gut refuses to offer any guidance, consult your friendly HR rep. Or, if you feel comfortable, chat with your manager. I sincerely doubt anyone will dock points or giggle at you for asking earnest questions about what you can and cannot wear to work/with clients, but if they do? Better get that embarrassment and aggravation out of the way up front, and feel confident of your choices moving forward.
So. Here are some ideas to ponder if you aren’t sure how to balance what you want to wear with what you’re expected to wear:
One envelope-pushing item per outfit
As Maddie guessed, it’s gonna be easier to get away with a leather pencil skirt if you balance it out with something from another fashion family – something soft or retro or colorful. Something distinctly NOT tough, edgy, or sexy. Juxtaposition is your friend, and can help you slide a few items aligned with your personal style into outfits aligned with your boss’s expectations. (Or your friend group’s or your in-laws’ … this works in multiple settings.)
Accessories generally get a pass
If you’ve got a dress that you think is toeing the line, you’re probably better off relegating it to weekend wear. But aside from anything printed with obscenities or designed to be reminiscent of genitalia, most accessories are easier to incorporate into conservative, work, or client-facing outfits. OK, you might not want to wear a black leather dog collar or five-inch perspex heels … but chunky necklaces, funky shoes, stylized eyeglasses, unusual watches, and sculptural handbags will simply create interesting contrast against more conservative clothing.
More coverage = less kerfuffle
And here we delve into irritatingly patriarchy-related territory: Most people are more willing to accept unusual, edgy, or stylized pieces if they offer coverage rather than being revealing. Which is stupid and confining, but can also be used somewhat subversively. A skull-print top that’s sleeveless and low-cut will turn heads, but a skull-print scarf worn with a crew-neck and blazer might not even register. A leather miniskirt will cause a stir, but a leather miniskirt worn with opaque tights and knee-high boots could pass muster. If you’ve got something you know to be controversial, wear it in a mix that errs on the side of more coverage.
High quality, good fibers
Clothing that’s well made and created using high-quality fibers will generally make its wearer look sophisticated, even if it’s done up in wild shapes or funky prints. If what you’re wearing is both cheap and borderline-inappropriate, it’s more likely to attract attention. Which doesn’t mean you should start buying super-expensive clothes that might get you in trouble with your manager! Just know that you can get away with more envelope-pushing personal expression if you make sure to keep some top-quality items in the mix.
Very few of us are privileged enough to have total freedom when it comes to style choices, and it can feel stifling to conform to employer or social expectations. But there are always ways to make sure your unique style shines through, and I hope some of these will prove helpful to you. And to Maddie!