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  • Writer's pictureJen

Bored With Your Style?

Updated: Jan 21, 2022

Last week at Trader Joe’s, this woman caught my attention (in Vermont this time of year we’ll be wearing our winter coats one day, and sandals the next!). I couldn’t quite figure out why I was so intrigued by what she was wearing, so I decided to snap a picture and think about it when I got home....

Later that night I wondered if it was the leopard jacket that was catching my attention since leopard is a huge favorite of mine. As a jacket, it’s not something to wear when you want to play it safe. There’s no fading into the woodwork while wearing something like this! Even though I like the leopard and how the cranberry bag pairs with it; there was something else going on here that I was stuck on.

Was it the iridescent sneakers? Those are fun. I like an exciting shoe, and those definitely fit the bill. You gotta love sneakers for running errands. Stylish slip on sneakers will be on my list for spring (when it finally arrives up here!).

How about that scarf? I remember wishing I had thought to throw one on before I left the house. It was cold waiting in that line! (37 degrees, folks!!) I also loved how this woman’s stylish short hair leaves lots of room for the scarf to be seen.

Maybe I should cut my hair? No, that wasn't it.

I finally realized that the simple answer to why my eyes had been drawn to her is that I just admired what went into the whole look. Her combinations were unexpected and a bit risky. There was no matchy matchy going on here. Could it be that the idea of wearing something unexpected and a bit risky was appealing?


Here’s a few things that this sighting helped to clarify for me:

Risk Tolerance: Just like an investor can have a portfolio of investments that have high, moderate, and low risk, so are the assets that we stock in our closets. I’ve gotten stuck in filling mine with no risk assets. That could be one of the reasons for the “I’ve got nothing to wear!” syndrome. Diversify, friends. Diversify.

The appeal of the unexpected: Matching and coordinating is all well and fine, but where’s the (yawn!) line? When you’re feeling BORED with your clothes, it’s probably worth taking some time to think about whether you need to try mixing it up a bit. Even if it's just something small, it can add a little fun and excitement for your enjoyment only.

What are you afraid of, anyway? Fear can keep us stuck in the status quo (unfortunately, you are hearing from an expert on this one). It may look different for you, but fear is my Achilles heel. Dressing to look like everyone else or to fade into the background definitely squelches creativity. Challenging yourself to up the risk tolerance a bit at a time will hopefully get you on the road to trusting our instincts.

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