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How to Tell Your Best Friend to Change His Clothes: A ‘Sleepy Hollow’ Advice Column for Abbie Mills

How to Tell Your Best Friend to Change His Clothes: A 'Sleepy Hollow' Advice Column for Abbie Mills

Dear Captain Awkward, 

My good friend and colleague wears 18th century period dress all
the time. Every day. To work. (We do not work at a historical re-enactment
tourist attraction.) I’ve tried buying him gifts of new clothes that he might like,
in case it was an issue of him not knowing or not having other things to wear,
but he’s rejected all of them and keeps wearing the same old cosplay duds… every
single day. Without laundering them. He’s a wispy white dude who talks like
he’s out of a history book, so I guess the look suits him to some extent, but
he doesn’t smell so great up close and we do have to spend a fair amount of
time in a car together for our jobs.

In addition, the clothes immediately make people think he’s a
weirdo and take him less seriously and I worry that people who see us together
take me less seriously on the job. I am a black woman working a dangerous job
in a mostly white community, and sometimes my safety and the safety of others
depends on winning people’s trust and getting them on board with unusual
circumstances. We need all the respect and credibility we can get. I could
bring up the dress code, but our boss is way too distracted with other things
to enforce it. How can I coax my friend into this century?

Sleepless in the Hollow


Dear Sleepless,

If your boss isn’t enforcing the dress code, my advice is to
address the hygiene issues, if there are any, and leave the clothes thing alone
unless the clothes actually smell. There is no good way to say “You
smell,” so if he smells, you just gotta say it: “Friend, this is
awkward, but you don’t smell so good today. Do you need to stop by your place
for a change of clothes and a shower? Please, take all the time you need. I’ll

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Other than that, up to a certain point, adults get to pick out
their own outfits and deal with the consequences of how they are perceived by
others. I had a coworker once who wore his “Star Trek” uniform during
Casual Fridays at the office, and I thought it was really weird and uncool at the
time, but now I look back and I envy that guy for his ability to give zero
fucks and just have goofy fun with his life. I also went to undergrad with a
guy who dressed like Vladimir Lenin every single day, complete with shaving his
head bald and never wearing zippers. It was odd, but there is something
compelling about a person who dresses exactly how they want to look, and I can
still remember how he looked all these years later when most of the J. Crew and
Abercrombie-wearing people have faded from memory.

My safety didn’t depend on them, and come to think of it those
were both white guys of a certain economic class and education, so you are
right in that what is “charmingly eccentric” on a white dude would
not fly for others. And it’s not fair. It’s okay to be irked. It’s okay to drop
a word to your boss if you think it will help. As your friend, do you think he
is sensitive and open enough to matters of race and gender that you could
explain why this matters to you? “I don’t want to change you, and I want
you to be comfortable, but at work, we need all the credibility we can get and
I think that if you dressed less oddly it would help us with our work.”

If you did want to try the gifting route again on his birthday
or a holiday, try getting him clothes that are in the same vein as what he
wears now (perhaps at the local theater company’s annual costume sale), or make
him an appointment with a tailor to have something constructed. There are many
variations on the pants/shirt/jacket combination of menswear and perhaps
something that bridges the difference could be found. More sets of clothing =
more options for laundering = better smells! Plus, a gift that says “I
really see who you are” is almost always better than the gift that says
“I want to change you.”

However this plays out, I think it would be good for you to take
a deep breath (though… do that out of his smell-zone) and do as much as you can
to mentally consign your friend’s clothing to something that is his problem
alone to worry about. We all feel trepidation and worry when people close to us
make choices that we don’t agree with, but people really do not thank you when
you weigh in on certain things (what they wear, what they eat, whether they
remain obsessed with their exes long past the point that we roll our eyes at
the mere mention of this person, etc.), even when it is done from a place of
love and concern.

You sound like a serious and respectful person, and anyone who
meets you for more than five minutes will get what you are about. Your friend won
you over despite his clothes — trust that he can do the same with others. In a
dangerous world, we need friends who accept us and look out for us more than we
need friends who shield us at all costs from our own mistakes.

Jennifer Peepas is a Chicago-based filmmaker and film teacher. She answers questions from non-fictional characters at her blog, CaptainAwkward.com. 

READ MORE: Fall 2014 TV Preview: Mondays Seem Dark in ‘Gotham’ But There’s Fun to Be Had in ‘Sleepy Hollow’

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