Josh Rubin has always had a knack for unearthing beauty in the unexpected. With his interest in photography emerging at the tender age of eight, Josh’s sharp eye and endless drive soon merged with a love for technology, led Josh to a career in product design and created the foundation for his greatest venture. What started as a side project, a personal website used to display and share various amazing things he discovered on the web and IRL, COOL HUNTING has since accelerated into an award-winning online publication. Josh and his husband, along with a global team of contributors, work to produce head-tilting, self-reflecting, and mind-opening visual stories with a purpose. We met up with Josh to discuss the challenges of a work-life balance, the difference between trends and patterns, what exactly makes an outfit “cool,” and how Weejuns play into his eclectic taste.


You started COOL HUNTING in 2003 as a way to organize and highlight things you were interested and inspired by. Seventeen years later, how much does your personal taste influence what you share on the site? Do you ever feature things you don’t personally think are “cool” but think others might?

That ethos still plays through what our team chooses to share. We only cover one out of every hundred or so things that we see. And the stories we publish are always ones some or all of us feel personally connected to. We believe “cool” is an emotion and therefore subjective. If we start to worry about what the audience thinks is cool, we’ll lose our way.

You once said that COOL HUNTING doesn’t report on “trends,” so much as it points out “patterns.” How does being (or not being) part of a larger pattern affect something’s coolness? When does a pattern become a fad or a cliche?

Some things we find to be cool are islands unto themselves and others are part of bigger patterns. We like really obscure, niche-y things like eclectic collections of objects (like the International Banana Museum), but we also like a good backstory, even if it’s tied to a very mainstream product (like Apple Watch Screen Designs).

What interesting new patterns have you been seeing in 2020?

Though it’s been ongoing for years now, the upcycling movement is mainstreaming this year and we’re very happy about it. From indie brands like Atelier & Repairs who made the camo pants I’m wearing in one of the looks, to Nike’s Space Hippie program, reuse and style are colliding.

Since COOL HUNTING‘s inception, you’ve shared business responsibilities with your husband, Evan. What’s it like working so closely with a partner like that? Do the lines between blur between business and personal?

Evan and I work really well together and prioritize clear and constant communication, so sharing responsibilities runs pretty smoothly. The lines between business and personal definitely can get fuzzy, though. We are often working from home or on the road and even on the rare occasion that we try to take a vacation, we can’t help but meet people and find things that would make great stories for COOL HUNTING.

You now host travel experiences to places like Zambia, Cuba, and Morocco. What made you start doing these trips? How do you see it as an extension of the website?

COOL HUNTING trips are an extension of our editorial. Instead of waiting for us to report on a place we visit, we let readers come along for the exploration. For our latest trip to Japan, we married it with our product development and retail program, COOL HUNTING Omakase. We worked with several Japanese artisans to make an exclusive collection that we sell through our site and our guests were able to meet these artisans during the trip. All along the way, we captured a ton of content to share through our channels.

What makes an outfit “cool,” in your eyes? How do Weejuns fit into that?

What makes an outfit cool is how you feel when you’re wearing it. To me, feeling like my outfit is an outward expression of who I am inside is key. But I can be moody, so the style changes day-to-day or week-to-week. In general, my style is a bit eclectic, with inspiration from Japan seen through a hippy-ish lens. I love an unexpected twist, which is where Weejuns fit in.

Josh's Questionnaire

Photography: Aaron Bengochea

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