Do you wear hats? I love hats (obviously) but every time I put one on outside of Derby season, I feel like a big try-hard. Anyone else feel that way?

My goal is to look effortless and chic (a la Jacey Duprie) but Drew always ends up calling me Indiana Jones and I get a complex. But hats are so fun and the easiest way to make even the most boring outfit more interesting (see below).

So how do you abandon your fears of looking like a cowgirl and channel your inner cool girl. Well, my first tip is to stop giving a damn what your husband thinks of your outfit (that’s me reminding myself).

Beyond that, I like to stick with a couple tried and true tricks for styling a hat like a pro.

* Stick with a neutral palette. Start with your hat and then pick your color palette around that. I love to pair a tan neutral hat with a simple black dress or jeans, a t-shirt and booties. It elevates even the most simple look and adds a bit of edge.

* Top off a dress. Think about Derby. It’s all about dresses and hats. Bring that same level of commitment to summer, fall and winter. Whether it’s a midi fall floral or a simple black maxi, either one will look put together topped with a simple hat.

* Avoid doing too much. If you try to do too much, you can look a little costume-y. If it feels like you’re wearing a costume, you probably are. So I avoid looking like Indiana Jones by sticking to sneakers or simple flats instead of jeans and brown boots. Maybe don’t go full cowgirl and pair your dress with boots (unless that’s what you’re going for and in that case, go full Dolly).

* Search IG Hastags for Outfit Inspiration. This is what I do all the time for just about any kind of outfit. Search #hatstagram #hatstyle or any number of hat associated hashtags to get some real life inspiration. You’ll probably see just as much that you don’t want to do as what you do but it’s a great way to see how you can use what’s already in your closet to style up something chic.

Go Buy a Hat

American Eagle Waffle Knit Oversized Sweater
House of K Hat | Madewell Mid-Rise Skinny Jeans 
Suede Booties (old, similar here)

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Photos by Tabitha Booth