Cool shirts. AI art

How to Choose Cool Creative Dress Shirts

Wardrobe Tips

Michael Filimowicz, PhD
AI and Men’s Fashion
3 min readFeb 27, 2024

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Distinguishing the truly creative from the mundanely mediocre is akin to finding a needle in a haystack. Or, more accurately, a needle in a pile of other needles, if one were to adopt the dry cleaner’s window as the ultimate litmus test for sartorial creativity. Yes, you read that right. The local dry cleaner, that unassuming establishment where garments go to shed their sins and emerge in sanctified neatness, holds the secret to identifying genuinely adventurous dress shirts.

Imagine this: You’re sauntering down the street, and there it is — the dry cleaner’s window, showcasing an array of shirts in a spectrum of sameness. This tableau of textile conformity is your oracle for fashion originality. If you’re about to invest in a new dress shirt and wonder whether it’s a beacon of creativity or just another drop in the ocean of sartorial blandness, take a mental picture of that dry cleaner’s rack. Now, hold that image in your mind as you contemplate your potential purchase.

If your chosen shirt would blend into the dry cleaner’s display like a chameleon, congratulations — you’ve found yourself a perfectly ordinary shirt. It’s the kind of shirt that says, “I am here to conform,” the kind that would make a stack of white paper feel like a carnival of diversity in comparison. This is the shirt that wouldn’t raise an eyebrow, let alone turn a head, in the vast sea of its identical twins.

But if, in your mind’s eye, your shirt stands out against the backdrop of the dry cleaner’s window like a peacock at a penguin party, then you, my friend, have struck sartorial gold. This is the shirt that defies the tyranny of the mundane, the shirt that whispers (or perhaps shouts) of a wearer who dares to be different. It’s the shirt that would make the dry cleaner’s clientele do a double-take, questioning their own life choices and wondering if they, too, should embark on a quest for something less ordinary.

This method, while seemingly unorthodox, is a testament to the fact that true creativity in dress shirts is not just about loud colors or bizarre patterns. It’s about standing out in a crowd — or in this case, on a rack. It’s about making the dry cleaner do a double count, ensuring they haven’t accidentally slipped a piece of avant-garde art among the sea of corporate conformity.

So, next time you’re shirt shopping, remember: the path to creative enlightenment might just run through the local dry cleaner’s window. Choose a shirt that would cause a stir among the starched and pressed legions of the ordinary, and you’ll have found a garment that truly deserves a place in your wardrobe. After all, in a world full of dress shirts, why would you want to be just another hanger in the rack?

Boring shirts.

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