Stylish Race-Day Hat Ideas From An Award-Winning Creator

May 10, 2019 at 11:14 am by RMGadmin


By Jenny Reimold

Racing season has arrived and if there is ever a time where bold fashion statements are encouraged, it is during this welcoming of spring. In a season where hats serve as the focal point of an outfit, it is important to plan your race day outfit to showcase your spring headwear. As last year’s “Best Dressed” winner at the Iroquois Steeplechase and after taking first place in The Hampton’s 2017 Easter Bonnet Parade, I have a few crafty tips on how you can create award winning looks on race day!

Having lived in Florida until last year, our Easter and Kentucky Derby party tradition always involved Lilly Pulitzer dresses for myself and five daughters. After striking out in finding coordinating hats, I began creating my own, over-the-top, fashionable bonnets and hats with floral blooms and craft hats found at Michaels. With no sewing skills and armed only with a hot glue gun and floral wire, my idea to design thematic derby hats and bonnets became a surprisingly huge hit! So much so, that local news anchors and celebrities began asking me to design these thirty-minute, party wear creations for them.

If you’re looking to make a statement this derby season and don’t want to spend hundreds on a derby hat that we’ve all seen before, create your own! My kids loved being a part of this process as well, selecting and choosing their own themed looks.

1. Start by purchasing straw hats or Easter bonnets with a STIFF brim. Hat deĢcor needs something to rest on so if your brim is floppy, you will only be able to decorate a small portion of your hat. I always buy the straw hats at Michaels that people craft for their front door. They come in a large size for adults and a small size for smaller children.

2. Choose a theme... I have designed hats centered around Lilly Pulitzer, Disney movies, a golden goose, the Pittsburgh Steelers, the Derby race itself, spring and flamingos. Any theme will do. Purchase small toy objects in your theme to add to your hat later... small horses, toy figurines, mini flags, smaller plush animals or dolls are really the award-winning pieces that make these hats stand out from the rest.

3. Buy a floral foam ring, floral wire and wire cutters. Place the ring over top of the hat to serve as the base for your florals. Secure the ring with the floral wire by simply poking the wire, starting underneath the brim of the hat, and twisting on top like a twisty tie.

4. Add ribbon! Hot glue one band of ribbon at the base of the hat, then cut two strips and poke each end through the side
of the hat to create chin straps. Tie a simple knot at the top and let the other fall loose to tie. Make sure you test out where to put the ties...I suggest just in front of where your ears hit the hat.

5. Purchase roughly eight floral stems with large blooms, about six tall, wispy springs of flowers and approximately ten small coordinating blooms to serve as the main part of your hat. Begin by cutting the blooms off just below the head, leaving some wire as an anchor and just stick those in the foam board, evenly, around the hat. Then, add some taller sprigs in the back and fill in with small flowers. You will want to arrange some of those florals on the main part of the hat that sits on your head. For those pieces, use wire bent in a “U” shape, starting from INSIDE the hat, and poke through to the top, securing your flower. Just twist the ends of the wire around a small portion of the hat like a twisty tie and cut the remainder off.

6. Add leaves. Cut single leaves from your stems and fill in the empty holes in your foam board.

7. Now add the fun stuff...using that same twisty tie method, begin securing all of your thematic objects with the wire. It is important to always begin inside the hat so that ends of the wire are on top of the hat, not inside where your head is. This was the rookie mistake I made in creating my first set of hats.

8. Top off your hat with any last-minute, final touches and practice wearing it. These hats can take a few minutes to adjust to as it becomes a bit of a balancing act.... as we all know, being fashionable isn’t always easy!

If you’ve created your own hat or have questions about the creation, reach out to me on Instagram (@jennyreimold ) or tag me in your own creation! Racing season is a party; dress like it!

Jenny is your Styling Your Everyday contributor. She will bring to you design and entertainment tips from her years of experience. Connect with @jennyreimold on Instagram or at