Let me start off by saying, if hats REALLY aren’t your thing…if you don’t have one shred of wanting to redeem yourself for that period of time in the early 2000s you and your friends all wore pinstriped fedoras to the Fall Fair, then good on you! If you, like me though, were dead set convinced that you were not a hat person, and the only time you wore a hat was out of necessity come Winter time…then this is for you. You CAN wear hats, you ARE a hat person; you just need to garner the confidence, and find the right hat for you!

I don’t know about you, but just saying you need to have confidence to wear a hat seems a little bit ridiculous to me. On one hand, it’s just a hat; people throw on ball caps all the time without a care in the world!

What I’m talking about is making a statement. A serious hat takes some guts, but it can be the perfect finishing touch to a fabulous outfit.


I know this is an obvious one (start your eye roll now), but as that annoying saying goes “you won’t know till you try.” I was utterly convinced that I looked terrible in hats, but I admired certain styles on other people; so when I was at a store I would force myself to try on hats. It’s also a great way to see what style works with your head size, and shape.


A big grievance I had early on, is that when I would wear hats, my head would either hurt from the band squeezing me too tight, or the hat was too small that I looked like I was wearing a tiny top hat. Like any piece of clothing or accessory, make sure it ACTUALLY fits you, so you won’t be cursing it halfway through the day.

Because if you’re a hat wearer…you know once it’s on, it is NOT coming off until you can reveal your flat head in the privacy of your own home!


Since hats can be such a statement piece, it’s important that you stay true to your personal style. If you know me, you know I’m all about the chic, classic glam; so a more trendier/street style look, such as a bucket hat, wouldn’t be the best fit for me. I personally love a Stockman, or a Panama style hat, because of their classic lines, and often neutral colour palette. Hey! That’s another good tip…start with a neutral colour.

I also recommend diving into Pinterest to see how other people, whose style you resonate with, style hats into their daily outfits. It acts a a great guide, especially for when you’re feeling a little self-conscious.


Dirty hair days! We all have those days when you don’t have time to do your whole washing/styling routine (especially if you have curly hair!), or your hair is on its second…fourth day…throw on a cute hat! I especially love styling my hair in a low messy bun, and pulling out some tendrils in the front for a really romantic, and chic look.

To finish off, let’s talk about hair real quick, especially curly hair. I think one of the main reasons I thought I couldn’t pull off hats was because growing up, all I saw in magazines were women who had long, thick, wavy or straight hair. The kind of hair that takes little effort to look good, what I used to think “hat people” looked like.

There I was with my shoulder length curls, not looking like the glamazon I thought I would wearing a hat…which is why finding people who have similar hair, style etc. is so important. When you see it, you can believe its possible.

So no matter your hair type, just know that you are beautiful, and you can wear a damn hat!


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