Cool Girl Fall Series: Wool Fedora Hats + White Button Downs

Welcome to Cool Girl Outfit number 2 in the series! If you missed the first outfit, Denim Jackets + Black Distressed denim, click here!

To kick off outfit number 2, this right here is the ALL SEASONS BASICS. There is nothing more transitional than a white short sleeve button down! Play it up in the spring with a silky scarf around the neck, or here, pair with a statement belt and wool hat. The open toed booties also work well for this summery September weather, but the outfit can easily transition into colder winter months by adding warmer boots and a long open cardigan.

Are you starting to see the one thing in common among these cool girl outfits? The individual pieces are TIMELESS and TRANSITIONAL. They are classic pieces you can wear over and over, in multiple ways, creating an endless variety of outfits from season to season with just a few changes. Now that’s why it should be called a cool girl outfit, because it’s PRACTICAL, and that’s pretty cool to me.

The Anatomy of Cool Girl Outfit #2

White Short Sleeve Button Down

A closet essential really. Works for work, for meeting friends, for brunch, paired with skirts, paired with jeans, paired with shorts….mix it up with accessories like little silk neck scarves….the possibilities are endless really. I highly recommend one of the Madewell shirts.

High Waisted Distressed Denim

This fall, the mom jean trend is totally in. I still haven’t bought a pair though, because I’m still rockin’ these Levi’s, and the Free People Busted Knee Jeans that are normal tight jeans. First picture below below is the Free People, 2nd is the Levi’s. Please ignore stain on the Levi’s…not sure what it is or if it’s coming out but I wear them anyway. Can it be like a house, it just adds character? P.S. I sized up in both brands.

[Fedora] Wool Hat

These will never go out of style. This is one of the first fedoras I got over 4 years ago. Now I’m looking to invest in something more sturdy, like the amazing Lack of Color hats. 


Since you have such a neutral outfit, you can REALLY play around over here! Pattern all the way works here, I just happened to pair it with open toed booties this time around. This outfit is where you can break out those leopard or snakeskin booties if you’ve got em! Or get them now! All my bootie picks below!

Statement Leather Belt

The Gucci Belt is not a realistic purchase for everyone, so I found some amazing leather and faux leather belts with statement belts at affordable prices, starting at $16! Threw in a few leopard belts in there too, because who doesn’t love leopard?



Hi, I'm Anna!

Welcome to the corner of the internet where you’ll find boho & bright style, travel adventures, and life in my latest “hometown” – Nashville, Tennessee. My love and I recently bought a house – and we’re taking on the renovations ourselves! You’ll be seeing more home content here – from DIY tutorials to home decor inspiration. We have a LOT of ideas for this house, implementing slowly one room at a time!

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