Kind of Cool

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Dress Like Your Character

Dress Like Your Character

a fun way to unlock a new level of knowing yourself

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G F
May 22, 2025
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Dress Like Your Character
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Last week, paid subscribers (huge thank you btw) unlocked twelve films that have refined my eye for detail. By which I mean, I’ve watched them so many times that I found myself observing them and borrowing their aesthetic elements in order to shape my every day reality. Might sound oh so very blah, but I mean it in a non-blah way, I promise. That piece is kind of connected to this one, but not a prerequisite.

If you would like to access the full film list & the full version of this piece, upgrade to a Kind of Cool paid subscription (for less than the price of a viral pastry that turns out to be incredibly underwhelming)

Look out for The Simpler Times #03 in inboxes for all subscribers this weekend…


Forgive me, but any puns used in this ‘stack are intended.

me & u discovering our characters

Allow me to set the scene. You care about style, you love clothes, you want to dress better, you want to dress worse1, it’s starting to show that your mum still buys your clothes. Maybe you hate clothes and you’re hate-reading this. Whatever floats your boat I guess.

If any of the above rings a bell or ding! ding! ding! you’ve read to this point and you’re wondering when I’ll get to my point, it might be time to approach all you know (or don’t know2) about fashion, clothes and so-called “personal style”3 from a different angle.


The angle in question:

However you feel about film, I think we can all agree that costume designers are the real underdogs of movie magic. They take written concepts of an imagined person and turn it into a physical embodiment of an entire life up to a point. And they do this on a strict schedule. Yet most of us are still piecing this together many years later for the only character we’ve ever been, ourselves.

With this in mind, let’s consider that the key to your style questions might be found, or at least begin, with a character. Your character. It may seem obvious to some that “style comes from within” and it’s likely I’ve said that before, but I’m also learning about myself that sometimes it doesn’t.

If last week’s list of films is anything to go by, so many of my decisions, both mundane and artistic, have evolved from external inspiration. No wonder I talk about references all. the. time. We spend so much time cataloguing daily likes and dislikes, it’s only natural that they’re going to feed back into our self-expression. Seems potentially overwhelming and a little vague right now, I know, but it’ll make sense.

Below you’ll find examples and prompts to discover your own character style (plus some links to shop if you like).

Menswear Example: Thomas Webb (played by Callum Turner) in The Only Living Boy in New York (2017), costume designers: Ann Roth & Michelle Matland

You may know Ann Roth as the woman on the bench who smiles at Margot Robbie in the 2023 Barbie movie. I have come to know her, however, for what she is probably most famous for: her costume designing.

Her IMDB billing includes character wardrobes from many of my favourite films (see: Julia & Julia, Someone Like You, The Way Way Back, Working Girl). If anyone knows how to put together a character wardrobe that captures a still-intriguing essence of the everyday, it’s Roth. And for many of those films Michelle Matland has been by her side. The pair know exactly how to dress characters who truly (and regularly) live, but with enough enviable style that I have to pause the film to search for similar pieces online.

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