It is no secret that I love hats! They are the best at disguising a bad hair day and make you look stylish in an instant. My mom actually told me to write this post a few months ago because she pointed out that a lot of people (including her maybe?) are nervous about wearing them. And since I immediately associate hat wearing women as being bold and confident, maybe she has a point.

Hats have been really, really popular the past few years. But how can you figure out what you like and what looks good on you? Normally when I’m stepping outside of my comfort zone it’s because I’ve seen something I was unexpectedly drawn to and been inspired to try it. I take photos or save screenshots on my phone of these things all the time, and find that’s a great starting point when I want to try something new.

Here’s where to go from there:

1) Narrow it down

Head to the accessories section of a big store and try on a whole bunch of hats! Once you see different styles and colours right next to each other you can get a better idea of what you like/don’t like. Forever 21, H&M, TopShop or even department stores like The Bay usually have a good selection at reasonable prices. If you’re shopping alone, find a friendly sales associate (who is well dressed of course!) and ask them their honest opinion.

2) Stick to the classics

If you’re intimidated it’s best to stick to something simple. This is a great idea regardless because once you find what you’re looking for you will likely enjoy it for much longer. Neutral colours and classic shapes will always take you further than a something super bold and trendy.

3) Work your angles

The right hat might seem all wrong if it’s not sitting well on your head. Try it tilted further back or forward and play around with your hair positioning to find the most flattering and comfortable look for you. Getting the right size is also very important so it stays on your head and doesn’t flop around.

4) Don’t worry so much!

Fashion at its best is fun and makes you feel attractive and confident. Look for a hat that does that and you will wear it without a care in the world!

Forever 21: Small Brimmed Fedora (similar to grey hat above), Large Brimmed Fedora (similar to camel hat above), TopShop: Wide Brim Wool Fedora (similar to black hat above)