How to Pick the Perfect Derby Hat

It’s that time of year again: Derby Season! This means mint juleps, brushing up on the words to “My Old Kentucky Home,” and of course, hats!
Picking out the perfect hat for the Kentucky Derby – whether you’re heading to the big race in person or going to a fun viewing party – can be a daunting task. The good news is that I’ve been to quite a few Kentucky Derbies, both as a fan and in a working capacity as a photographer of fabulous hats, so I’m here to help!
The key to a great Derby ensemble is to pick out your hat first and get the rest of your outfit in place from there. So, first you want to make your decision: are you a wide-brim hat fan or a fascinator fanatic? I’ll give you a couple of examples of each style so you can decide what you’re most comfortable wearing.

First up: the wide-brimmed hat. These are the traditional chapeaux of the Kentucky Derby; they can be understated and chic or elaborate and ornamental; and they’re the perfect topper for America’s most famous horse race.
Sometimes at the Kentucky Derby, you want to go big or go home. That’s why I love this mint green confection that involves layers and ruffle detailing.

It’s a statement hat, so the outfit I built around it is fairly restrained. The hat can do most of the talking here; the dress coordinates with the millinery without competing, and the accessories are kept neutral.

15DerbyHatsGreen by penelopemiller featuring Dartington Crystal
I love the idea of adding subtle gold horseshoe earrings to the outfit; it’s both a nod to the equine competition and a great way to brighten up your face without the look getting too busy close to the hat.
Next up: sleek sophistication. I love this black hat that has feather and flower detailing, and it was a great base to begin an outfit.

I felt that this hat called for a more chic and sleek look, so I kept that in mind as I put together my imaginary ensemble.

15DerbyDreams by penelopemiller featuring Linda Farrow
I love how the shoes and the bag pick up the pink of the hat without being a completely bubblegum color; keeping the jewelry modern and geometric adds to the sleekness.
Our final wide-brimmed hat is a total classic – and something you can definitely wear again, whether it’s to the beach, to a wedding, or just to spruce up a summertime ensemble.

Since the hat has bit of a mustard-yellow tone to it, I opted to go with a pretty eggplant-colored dress to make the color pop. Since I didn’t want the jewelry to compete with the hues already employed in this look, I decided to go with restrained black and gold accessories. Also, I must have that tortoiseshell bracelet with the horse bit on it. I must.

15KentuckyDerbyComplimentaryColors by penelopemiller featuring a leather purse
More of a fascinator gal? No problem! I love those sleek, minimalist toppers; there’s something vaguely European about them, and with the right outfit they can look either delightfully retro or stunningly modern.
Red. The perfect color to wear to celebrate the Run for the Roses. I love this fascinator, which is architectural and feminine.

Which is why I replicated that effect with a structured dress and graphic accessories.

15DerbyHatsRed by penelopemiller featuring Diane Von Furstenberg
Each element here is deliberately chosen to highlight the care put into the pieces: the dress has subtle darting and ruching to create a dramatic silhouette; the shoes and bag each have strong lines that mimic the architectural aspects of the fascinator.
I love royal blue. It’s such a sophisticated color, and it flatters nearly every complexion.

The netting on this fascinator immediately took me back to the 1950s and ‘60s, so I chose a pretty floral dress in an A-line shape and boat neck to further add to the retro appeal of the look.

15DerbyBlue by penelopemiller featuring metal frame glasses
Some delicate T-strap shoes in a lighter blue that picks up on the dress’s subtler hues complements this, as do the rest of the accessories. It’s a vintage-inspired look that’s perfect for the Derby and doesn’t come across as too costume-y.
Our final look is one that highlights how fascinators can be the perfect topper for a modern Derby day look.

I love the graphic, almost abstract floral print of this dress:

15DerbyRose by penelopemiller featuring an oversized purse
Keep the accessories simple and metallic to let the fascinator and frock shine; and grab yourself a mint julep, because it’s almost Kentucky Derby time!