Finding the right hat for the Kentucky Derby is just as important as finding the perfect dress. Some say to buy the hat before the dress, and others say dress first. I don’t think there’s a wrong way to go about it, but I do like to secure my dress first, and then find a hat.

If you’re like me, you agree that the bigger the better when it comes to your Derby hat. I also firmly believe in finding a hat option that suits you, your hair and allows you to be comfortable. A few years back, I was busy stuffing paper towels in my hat to keep it from sinking on my head. Trust me, you don’t want that to happen. Finding the right fit and style can definitely be hard and expensive at the same time. Hopefully, my tips below will help guide you to finding your style at half the price.

Finding Your Hat

There are no rules when it comes to Derby hats. That can be a great thing, but it can also be a very challenging thing. Shopping guidelines usually help shape our decisions. Not having a set of rules to follow can make it difficult to narrow down your options. Keeping that in mind, I think it’s best to start with picking out something from your dress that you wish to highlight. It could be color or print, or texture. Find that something special in your dress, and look for a hat that enhances those features.

I also think it’s smart to try several hats on. To know what suits your style best, try on as many options as you see fit. If you are ordering online, I would order a few, and return the styles you do not choose. It’s always better to have options.

The two styles I recommend for Derby hats are fascinators and wide brim hats. I think these two are most flattering on all kinds of women. It’s important to note that you can find several different price ranges for these two styles. Start looking well before Derby, or if you are last minute shopping, Nordstrom, Macy’s, or Etsy are all good ideas.

Both fascinators and hats can be worn with any type of hair, short or long. I often think a pulled back updo underneath a big hat is the best route to take. You can also pull off an updo with a fascinator, or wear your hair down and curled. More on hairstyles to come, but either type of hat works in my book. Below you can find inspiration on past Derby hats that I think fit the bill for the big day.

Derby Hats

Styling Your Hat

I often take note of hat trends from the one and only, Kate Middelton. In general, her style is stunning, timeless and always classic. I appreciate her style and I often try to immolate her taste on occasion. The Derby is one occasion she would be best dressed. Seeking inspiration is always a good idea, as it paves a way for you to create your own look and style.

When I purchase a Derby hat, I try to keep in mind how often I will wear it before I break the bank. Hats can be very expensive, especially the big and elaborate ones. I always try to find a way to re-style my hat for other purposes if I am going to invest. Going back to Kate Middleton, I feel like a classic, timeless hat or fascinator is the best bet. You can always find a time or place to repeat the style.

More often than not, I gravitate towards a hat that has a disguise factor to its design. Whether it be with delicate fishnet or the way it lays, just slightly angled against my face. The way it fits and sits is the deciding factor of a really good hat. You can see in my pictures above, every look as that hidden or disguised shape to part of the hat.

Lastly, make sure you aren’t clashing with the rest of your look. The hat is meant to be the BIG accent of your outfit. If you’re a DIY goer, please be careful DIY-ing your hat. You do not want it to look like an arts and crafts project, or have it fall apart. Your look should be crisp and put together.

Derby Hats

Choose a Derby hat that represents your style.

Regardless of the price tag, the fabric, the shape or size, your hat should be a representation of you and your style. This is the one day where every woman can embrace her inner southern belle. Let your style shine and arrive at the Derby in a style you know you love and feel confident in.