Like You Mean It

Cupcakes & Cashmere jacket (c/o Shopbop)
Le Chateau top (c/o) (similar)
Grlfrnd jeans (c/o REVOLVE)
H&M heels
Looks Like Summer bag (similar)
Zara sunglasses (similar)
Mango hairpin
Keltie Leanne Designs necklace (c/o)
Mango earrings
Location: Bank of Montreal Main Branch – Winnipeg, Manitoba

It was an ordinary morning when I was walking to the bus stop, Minnetonka moccasins on for the walk and pumps waiting for me under my desk at work. And while it was an ordinary morning, I remember it because I looked down at my moccasins as I walked, wondering why I felt like moccasins and sneakers and other garments I felt comfortable in weren’t really good enough for regular wear. I was probably twenty-six at the time. It must be because I’ve never thought I’m pretty enough for them, I mused. Casual clothes are for pretty girls who don’t need to dress themselves up. That’s not me. I need to work a little harder. What a way to talk to yourself. I wish I could say I didn’t mean it, but I absolutely did.

Just a few years ago, wearing this kind of outfit would have been unfathomable to me. Especially if we were planning to take photos. I eschewed effortless outfits in which I had a chance of actually feeling comfortable, preferring dresses and heels because they were easier to hide behind. If everyone was looking at my tulle skirt, they wouldn’t be looking at me.

I don’t know where that deep-seated feeling of never being good enough came from. But for most of my life, there was a little voice in my head that told me it didn’t matter what I did – I would never really be pretty enough or thin enough or anything enough. I had to make a conscious effort to let it go. Some days, letting it go still feels like work in progress. But now, when I say to myself, You’re doing pretty well, I mean it, in the same way, I meant all the awful things I used to tell myself. And I realise how remarkably strong my faith in myself really is, because I believe myself now, just like I did then. Sometimes, you just have to say something like you mean it to make it true.

When I look at photos of myself now, photos in which I mostly wear jeans and flat shoes, I am amazed by how much more at ease I look. Not because I was always pretty enough to wear casual clothes. The truth is, being pretty is really beside the point. I look at ease because I finally gave myself permission to wear the clothes I always felt comfortable in. And the fact that I’m happier for it shows.