Some wardrobe classics never age. Like the leather biker and white t-shirt combo. Or the shearling jacket and grey jumper match. However, for every timeless look, there’s one that will never work. Ever.

Some time ago, the events team at The Bold Italic was putting on a men’s fashion show. They asked content creator Jessica Saia to put something together for its promotion. After giving it some thought, Saia teamed up with Isla Bell Murray and took a detour from the normal route one could go about it. They made a do’s and don’ts guide filled with funny photos that “barreled off the rails of what anyone would ever think to do when dressing.”

“[It] sounded much funnier and more interesting,” she told Bored Panda. “I had a friend sew the super-deep-V-neck and my friend Luke modeled for the men’s outfits we’ve created. It was definitely one of the most fun articles I produced.”

More info: jessicasaia.com | Instagram

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“I’m certainly not a fashion trends expert; just someone who thought it’d be funny to explore ‘inverse cutoff shorts’ and wearing socks over your sandals. But I think there’s a spectrum of giving your wardrobe zero thought and way overthinking about trendy clothes,” Saia explained. “There are a lot of guys in San Francisco who seem to just wear whatever free clothes their company gives them with the logo on it, and I find these ugly outfits sort of uninspiring… but hey, people have different priorities. [For example,] my partner wears the same exact thing every single day like a cartoon character, and it works for him!”

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To those who haven’t found their look yet, Saia advised to just mix the familiar with the new. “Everyone has a favorite shirt or sweater; think about what you like about it and then try to find things that have those elements to it. Also, trying on a certain kind of jacket or pants that you’ve never worn before can be really surprising. No matter what the style is, having things fit makes a huge difference. And it’s worth remembering that the fashion industry is the second-largest polluter in the world, just behind the oil industry; so getting things that last or shopping at second-hand stores is a good way to go.”

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