How do you all feel about big hats? I have a bit of a love/hate relationship with them. Love the way they look. Hate how they make you feel like you’re walking around with one of those cones dogs wear after they have surgery.

When you’re wearing one you’re stuck doing that dance where you can’t get too close to people, you have to do that weird head tilt to take pictures and getting in an elevator is damn near impossible. But the look, the look is great.

Because I love running around Churchill Downs like a kid on Christmas morning, I usually opt for a fascinator for Derby. You can still go for something impactful but it’s a lot easier to navigate life. I think if I had super fancy seats, I’d do a hat though. There’s just something so regal and out of character about a big hat.

French Connection Future Cornucopia Fit and Flare Dress
from Dress & Dwell 
Headcandi Hat 

If you’re looking for something big, this Headcandi hat will do it for you. The color on this one is so light and airy that it doesn’t feel like as big of a commitment as maybe a black or navy number. Plus, I love the feathers. Give me all the feathers.

I’m also a big fan of a fit and flare style – if something works for your body type, stick with it. It highlights my better half (the top) and helps hide away any of the less toned parts (the stomach area). You may not be able to see all the subtle colors in this dress but it lends itself to pair with a lot of different color hats or headpieces. Best of all, it’s under $150. 

More Fit and Flare Styles:

And if you’re looking for a full head to toe look, head over to the Dress & Dwell Derby shop. You can get everything you need in one stop. Or head over to my Derby Shopping Section for lots of options (if you have trouble with the tabs, just reload the page).

Photos by Tabitha Booth