Hacks, hobbies, and side hustles: Big hats

Caitlin MacRae’s yearly contribution to a Kentucky Derby tradition

A photograph of four colorful, and elaborately-decorated (with feathers and flowers and ribons) women's straw hats.

Hacks, Hobbies, and Side Hustles is a for-fun internal presentation series that began as a one-time event and fast became a popular way for us to get to know our talented colleagues. It has only two guidelines: finish in five minutes and focus on a passion that exists outside of Adobe. Learn where creativity takes the members of Adobe Design when they’re not working.

I’m a user experience research manager with a singular creative talent: making Kentucky Derby hats. For anyone unfamiliar with it, the Kentucky Derby is a horse race that happens every year and it’s steeped in tradition—primarily the traditions of wearing big hats and drinking Mint Juleps.

I’m not super invested in the outcome of the Derby, or horse racing in general, but I’m really into fancy hats and excuses to throw parties with my friends. I’m here to impart the secrets behind my process in case you too would like to make your own silly hats someday.

A photograph of a chestnut brown horse, with darker brown mane and tail, wearing a number 9, standing at the edge of. a racetrack.
The horse in this picture is a horse I used to own that ran the Kentucky Derby scene in the movie Secretariat . So, he was NOT a racehorse, but he played one on TV.

Typically, my hats are created in service of preparing for a party and hanging out with my friends. My supplies are standard: A hot glue gun plays a prominent role along with florist wire, scissors, ribbon, and anything else that’s small enough and light enough to wear on top of my head for an entire day. The primary thing to remember is that these hats can be embellished with anything so it's a time to be creative and let imagination run wild.

Two horizontal rows of three photographs showing an assortment of crafting supplies: Top row left to right: hot glue gun, spools of ribbon, crafting wire and rubberbands. Bottom row left to right: silk flowers, scissors, a spool of taffeta.
If I had to choose a “most important” supply, it would be my hot glue gun.

Although creatively anything goes, I’ve developed a five-step design process that works for me year after year:

1. Inspiration

Every year, about a month before I start working on a hat, I begin scouring the Internet to find inspiration. I usually start with image searches for big hats and save screen shots of anything that I fancy. I look for interesting color schemes, fun decorations, and creative ideas. Eventually I start mixing-and-matching ideas from everything I see that I like to form some sort of idea or concept of what I’d like to put together. With those ideas in mind, I shop.

A collage of five photographs showing details of elaborately decorated women's straw hats. Left: black feather details and a fuschia silk flower and lace (top); pink and white ribbon and a pink fower on a white straw hat (bottom). Center: a white straw hat embellished with black lace, feathers, and white-with-black-polka-dots ribbon. Right: a simple black straw hat with a black-and-royal-blue flower, and black ribbon and feathers (top); a fuschia pink straw hat with fuschia pink ribbons, lace, and flowers (bottom).
Feathers, lace, ribbons, and flowers, in any combination, are all without restraint in hat-making.

2. Shopping

Shopping typically involves finding a big plain hat with an interesting shape, then wandering the aisles of craft stores to look for supplies to decorate it. Wandering is a key source of inspiration since my designs typically come together through a mix of whichever “base hat” I end up getting and whatever supplies are available. I go into craft stores with a basic idea of what I’d like to put together, and I leave with what’s available. Once I have everything together, I start putting the details in place to begin my assembly.

Two photographs of aisles from a craft store. On the left an aisle of ribbons and on the right an aisle of silk flowers.
Aisles and aisles of supplies may look daunting but it’s an opportunity to let my creativity run rampant.

3. Assembly

Very straightforward, assembly consists of gluing things to a hat. But first it can also require me making some of the embellishments myself. I do some amount of combining and creating the different components that will eventually be attached. I put things next to each other, see how they look, and loosely arrange and rearrange to get a feel for the style and shape.

Once I’m happy with how things look. I take out the glue gun. The fun really begins once I start attaching lower items around the base and building up... even though there’s usually an accompanying flash of panic about whether it will all come together.

Three photographs of hat embellisment in progress. Left: A hand, with pink nail polish, wrapping ribbon around a piece of wire (top); an assortment of crafting supplies including fabric, spools of ribbon and thread, crafting wire, silk flowers, scissors, and a glue gun (bottom). Right: A white straw hat with light and dark blue silk flowers, and spools of light blue ribbon and taffeta laying across it.
Assembly is a lot of trial and error until it all looks great and stays in place.

4. Adjustments

My next step is to put the hat on, see how it looks, and adjust decorations and flowers as I need to. These adjustments usually involve tightening up the flower arrangements, adding small details to balance out the design, and making sure it looks good from every angle. I try the hat on several times to make sure that the decorations are in the right spots and that it frames my face the way I want it to.

Two photographs of the same hite straw hat with light and dark blue silk flowers, light blue ribbon and taffeta, and wire spirals wrapped in light blue ribbon. .
Sometimes I end up making the embellishments for my hats; the spirals in this photo are wire with ribbon wrapped around them.

5. Enjoy

Throw a party. Invite some friends. Make Mint Juleps. Ask everyone to wear a hat. Watch the race. And just enjoy the day.

Four photographs of an oudoor gathering. Top row left to right: Nine people, some wearing fancy hats, smiling for the camera; a plate of cheese and crackers, a bowl of berries, and a Mint Julep. Bottom row left to right: A mini bar with the ingredients to make Mint Juleps (bourbon, sugar, sprigs of mint); four women in fancy hats smiling for the camera.
It’s not a party if my friends don’t also show up in hats.

As much fun as it is, there are a handful of challenges with Kentucky Derby hat-making:

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