Wearing hats can be super intimidating!! I always see women wearing beautiful wide brim hats during the fall and think it looks SO good but my comfort level usually starts and stops at a ball cap or a toque in the winter. Why are they so scary to wear sometimes!? I’m convinced these dressier hats won’t look good on me, or mostly that I just couldn’t pull it off. And I feel like this is a popular opinion among a lot of us. But the truth is- that’s all a big load of you know what.

The amazing Rachel Hollis said, “maybe the hardest part of life is having the courage to try.” Even if it seems to be about something as silly as a hat- it’s going to look good as long as you’re confident in it. The easiest way to pull off a great hat is to put it on your head, and rock it! Simple.


I absolutely love this one from Banana Republic! If you want a great hat to start with, this gives the whole feel of those beautiful wide brim hats, but this one isn’t too wide! It’s a fedora-style felt hat that comes in two different sizes. I love this one because it’s sturdy but still soft and cozy! It’s the perfect accessory to a fall outfit (especially when you’re on day 4 of dry shampoo and want to look cute but just aren’t ready to give that hair a wash yet LOL).

(Click the images of hats to shop!)


I think that if you’re giving it a go you should definitely stick to a neutral so that it goes with everything you already own. Black was kind of a no-brainer for me lol! But there are also beautiful options in grey and brown as well, like these:


I love all of these options! Don’t be intimidated ladies- buy the hat, put on the hat, and ROCK IT!! Don’t waste time thinking you can’t pull it off. You CAN and you will!!

Outfit Details

Skinny Stay Black Ankle Jean

Featherweight Long Sleeve Strip V-Neck {this exact shirt is from a couple years ago but this is a similar style!}

Sole Society Oversize Blanket Scarf

Chinese Laundry Springfield Mule Bootie

Black Handbag {this exact bag was a gift from a few years ago- here’s a similar, budget-friendly version!}