“Style is knowing what suits you, who you are, and what your assets are. It is also accepting it all.”
– Bianca Jagger

Lo these many years ago in my early 20s I decided to sit down and figure out what I actually liked and wanted to wear, as opposed to trying to follow trends or simply copy looks I liked on other people (which invariably never looked as good on me). It was a surprisingly frustrating exercise. It took a few years in all honesty, and I ended up going down a few blind fashion alleys, and frankly spending more money than I should have, along the way. But I was sick of owning clothes I didn’t wear because I’d bought them liking the idea of the pieces more than the pieces themselves…which was ultimately my personal breakthrough moment.

Liking and owning are not and need not be the same thing. I’d gotten them dangerously confused–something I think it’s very easy to do in our culture. Indeed, we’re kind of trained to. Just because I liked something didn’t mean that 1) I needed to own it or, 2) that it would necessarily suit me anyway. I didn’t really know what I liked, and as a result I was flailing–stylistically as well as financially or practically. Dividing aesthetic appreciation from my consumer urges helped get poorly planned or whim purchases off the menu; I then decided that I needed to figure out what my tastes actually were before buying more stuff.

I made a Pinterest board where I pinned fashion images that I liked, as opposed to items I wanted to buy.

Gradually, some noticeable themes started to emerge from the inspiration images I collected. What I learned over time is that I like masculine inspired tailoring in feminine clothing, neutral basics paired with colorful or standout accessories, high impact glam for special occasions, and a noticeably vintage vibe running throughout. Got it! If that’s how I buy, I know I’ll be pretty happy and get a lot of use out of my clothing. So it was and so it has remained.

I’ve never read any good style advice that didn’t boil down to, “Know thyself,” but I think if we are honest, that’s more difficult than it appears at first blush. Lots of us go through multiple identities or personas in our life–high school cliques, groups of friends, career moves, family changes–which means that who we are is constantly shifting. Sometimes we deliberately decide to explore new facets of our personalities, which may prompt a change in aesthetics. Sometimes…we just feel bored or frustrated with ourselves and an easy way to feel different it to choose to look different (let’s share tragic haircut choices in the comments, shall we?). And sometimes, our tastes simply change. Mine have shifted several times over the last decade. And even though I’m pretty happy with my wardrobe now, I’m fairly sure it will evolve again at some point as my professional or lifestyle needs shift.

Committing to examining and developing your sense of style can be an exercise in radical honesty, it forces you to really define what you like but also why you gravitate towards it. You may encounter some uncomfortable truths. When I was first freelancing full time, I spent several months in full schlub mode and there was a period of time where I could spend whole days in my pajamas if I wanted to, which I often did. It ended up having a knock on effect on my health (it was easy not to exercise) and confidence (it was hard to feel competent with perpetually messy hair). When I woke to this cause-and-effect, I made a switch and deliberately discarded or repurposed my lazy loungewear so that wearing it simply wasn’t an option. A minor change, but one that has had long term positive benefits for both how I look and feel in the mirror.

Examining your style can also open up some positive doors or new facets of your personality you want to explore and bring to the fore. Stay tuned for the story of my love affair with lipstick next week! Once you discover what you like (what you really like), I find that a lot of the imposter syndrome, self consciousness, or indecision that often comes with getting dressed in the morning melts away. If you genuinely love what you own, whether it’s trunk fulls of designer labels, or well loved jeans and t-shirts, I think you are much less likely to be concerned with what other people’s opinions are on the subject of your presentation.

Get to know yourself. Like yourself. Dress the part. It’s a formula that works for me, even though the first element of it is constantly in a state of flux.

Your turn! Have you ever tried to define your own sense of style? What tools helped? Could you sum up your fashion sense in three words or an image like that of the Great and Good Katherine Hepburn?