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Being human means we’re a wild and wound up ball of emotion. That’s the best and the worst thing about being us. What I’ve found is — as we change and grow, the way we express ourselves does too. The things we choose to wear and the objects and environments we surround ourselves with can be a powerful outward expression of that inner journey. But one emotion can stunt and hijack both that inner journey, as well as how it’s outwardly expressed:


As a younger fella, I allowed fear to dictate much of my experience. (I think we all do in different capacities.) I wanted to be accepted and I wanted to fit into a tribe, so I expressed myself in ways that were a giving-in to the fears of otherwise being rejected. Don’t get me wrong… I always cared about style and all these bits of fashion nonsense… but I constantly battled this little inner voice that reminded me of my teenage years when I felt judged by my dad just for briefly changing my hairstyle from a good Christian side-part to that quintessential late-90’s middle-part. I could spend an hour unpacking what my journey has looked like in coming to terms with my fears, but instead I’ll focus on YOU, and on three factors to expect as you confront whatever your fear might be when it comes to fashion. Here it goes:

Experimenting with personal style means you’ll probably get it wrong many many times before you finally get it right. That’s how literally everything in life works… so it’s OKAY to fail and try again. One day many years ago my ex walked into the bedroom and she started laughing hard at me and making fun of me. Why? Because I was wearing black skinny jeans, double-monk wingtip oxfords (fancy dress shoes) , a tacky striped tank-top, a fedora, and a gaudy gold watch… nothing about it made sense. But here’s the thing: I was trying. And the 2019 version of me looks back and applauds old tacky old version of me, because it was part of the journey. Swing, miss, swing, get a base hit, swing, get a home run. Just keep stepping up to the plate!

I remember standing inside the Goorin Bros shop in Portland Oregon… I saw their Dean The Butcher fedora, and I was drawn to it. I put it on, and loved it. I’m a also a slow adopter to new things… but I bought it anyway and started wearing it every day almost immediately. For literally months all I heard were jokes ranging from, “Hey there, Smokey the Bear” to “You need to give Pharrell his hat back!” The irony is, that brim has become a staple for me and it’s one of the best style purchases I’ve ever made. I was at a fashion event just two nights ago and someone from Goorin literally spied me out of the crowd and introduced themselves, saying, “I knew I recognized that Dean The Butcher!” Judgments be damned - just give it a try!

This is a good thing! Part of a journey of establishing a more specified style or sense of fashion means you’ll be exploring yourself more, and in so doing, deciding what you do and don’t like, what does and does not work for “you”, and establishing guidelines that will lead to easier buying decisions in the future, and you’l probably be surprised when you discover that this translates into other parts of your life as well. Developing taste for a certain thing means you will have a distaste for other things. That’s good because it helps you know what to say “no” to. The one word of caution is this: don’t get judgemental or arrogant. Stay humble and keep those newly choosey opinions to yourself! ;)

It’s all a journey. The key is to stay aware as we move through it. Cheers, dear ones.