If I scroll back a few years into the blog archive there are quite a few outfits that don’t feel like “me” – not to say that I’m embarrassed of anything I wore, it’s just that it would likely have been better suited to someone else. A floral kimono comes to mind.

The funny thing about defining your personal style is that it can take years to figure out.. but at the same time you kind of knew the answers all along. Think of the icons you loved when you were a kid. Mine were Jackie Kennedy, early Elvis and Dolly Parton and the cast of shows like The Wonder Years and Happy Days. I’ve always known that I loved tried and true American staples. A 50s-era full skirted dress, New England fisherman sweaters, borrowed from the boys vintage Levi’s and 70s-style stripes. It’s what I feel most myself in. So why did I try to fight it with those palazzo pants or that body-con dress? Maybe, like finding a partner, you just have to try things on for size. Even if you know they won’t be right for you in the end.

Years ago I wore a huge velvet bow headband to my Mom’s 50th birthday party. It was a whole look. But it felt like me. A little bit vintage schoolgirl prep, a little bit modern without trying too hard. My sister’s boyfriend at the time asked me if I thought I’d look back on pictures of the party down the line and regret such a bold fashion choice. I figured I’d see myself in those pictures and feel pleased that I was confident enough to wear exactly what I wanted at that moment. And p.s. exactly that style of headband happens to be having a major moment right now. But I’m willing to let bygones be bygones.

The point of the story is that if it feels quintessentially “you” at that moment, then wear it. Even if what feels like “you” shifts over time. Although spoiler.. I still love a good hair accessory.

I’ve been thinking a lot this year about my wardrobe and the fact that I’m a happier with fewer things, but ones that all feel quintessentially Jess. The funny thing is that back in my shopping heyday I would have found this idea sort of stifling, but in fact it’s been so refreshing. Every morning I get such a happiness boost when I look into my closet and realize I truly love everything in there. And when I go to add new pieces, I simply ask myself if I’d feel like “me” when wearing it.

Now if only I had saved that velvet headband…