Kentucky Derby: The Craziest Hats and Fashion Choices We've Seen so Far

The 2019 Kentucky Derby is upon us and that means in between all of the betting action and mint [...]

By Andrew Roberts

The 2019 Kentucky Derby is upon us and that means in between all of the betting action and mint juleps, we also have a bevy of fashionable looks to take in.

While some maintain a more reserved look for the Derby, others go all out and treat it like the fashion event of the Spring.

Colors flow, hats grow in size, and people from all walks of life attempt to top one another.

kentucky_derby_2019_hats
(Photo: Getty Images / Michael Loccisano)

This year is no exception and a fine selection of men, women, children, and pets are in attendance with their best looks on. Women have meticulously chosen their best Derby Day hats, coordinated outfits with their loved ones and friends, and even allowed their partners to go a little wild in the process.

And don't count out the men. There are plenty of men who have put aside the fashion norms of the past to embrace the wild looks of the Kentucky Derby.

It's all about the appearances and making your mark. Do these people make the cut? Scroll down and decide for yourselves.

Janice Dean

The senior meteorologist for the Fox News Channel and Fox and Friends staple got a pleasant compliment for her look on Derby day.

"My 10 year old son just walked in the room to see you and tv, and he said, "She looks nice." He never says anything like that. Love the hat!" a fan told Dean, leaving her to gush that the 10-year-old's comment "means everything."

Other news personalities on the scene also trotted out their best hats.

prevnext

'The View' former co-host Star Jones

star_jones_kentucky_derby
(Photo: Michael Loccisano / Getty Images)

The former co-host and founding member of The View brought a pair of looks to Kentucky Derby weekend. She wore the black number above on the red carpet for the Kentucky Derby itself. The former talk host and lawyer went in the opposite direction for the Kentucky Oaks one day prior, sporting a far more colorful hat and dress.

prevnext

Nene Leakes

Real Housewives of Atlanta star NeNe Leakes turned heads and got a lot of praise online for her sunny Derby look.

prevnext

Matching couples

View this post on Instagram

This has to make you smile, customized down to the bow tie...#houseofmacgregor #kentuckyderbyhats #customhats

A post shared by Cassie MacGregor (@the_hous_of_macgregor) on

There were also a few matching couples or friends doing their best to outclass each other at the event. The couple above sported a custom look from top to bottom, possibly putting forth one of the nicer looks on the day for a couple.

Others couldn't make it this year it seems but still wanted to share their style. Fashion writer Leckie Roberts shared these looks from prior years Derby events, including the behind-the-scenes tips about the fashion choices for each day.

View this post on Instagram

🐎 Running swiftly to get my Oaks Day Lily beverage! Happy Oaks Day y’all! 🐎 (Photos from 2018-2016) . - Oaks Day Facts - . .🌷Did you guys know the first Kentucky Derby Oaks was held on May 18, 1875? . . . 🌷the Kentucky Derby Oaks day is all about wearing PINK in honor of the Oaks official flower- The Stargazer Lily & in support of Churchill Downs’ official partnership with Horses & Hope. In addition, as part of this year’s “Pink Out,” Churchill Downs has partnered with breast cancer health program Northern Cancer Institute to cover the costs for normal breast cancer patients. . . . 🌷 Every year on this day there is a fashion contest held by @longines & typically run by @fashionattheraces 👉🏻 Head on over to her feed to watch ALL the fashion Oaks Day action! @cnl_designs . Download the @liketoknow.it app to shop all my looks!

A post shared by LECKIE | NYC (@leckieroberts) on

prevnext

Baby on board

Roberts also posted this fun shot from 2016, showing how no matter how fancy you look at the Derby, there is always some reality that might cut through to hide the glamour.

And others are proving that even if you can't make it Churchill Downs, you can still take part in the high fashion you see at the event. Have your own Kentucky Derby party.

prevnext

Joey Fatone

joey_fatone_kentucky_derby
(Photo: Michael Loccisano / Getty Images)

And don't you dare think the wild fashion choices are left only to the ladies on Derby Day. While most of the gentleman who attend the event tend to feature a reserved style, some have chosen to go a little crazier in recent years. *NSYNC member Joey Fatone is a fine example as he struts on the red carpet in his eye-catching getup.

Then again, there are a few who just decide that the weirdest hat possible can make fun during the day.

rose_hat_man_kentucky_derby
(Photo: Icon Sportswire / Getty Images)
prevnext

Bowties

If the ladies show off with their hats, the fellas and anybody who wants to keep their hair nice show off with their bowties. These are some of the best shared by WDRB's Marcus Green.

prevnext

Anna Nicole Smith's daughter, Dannielynn Birkhead

anna_nicole_kentcky_derby_hat
(Photo: Michael Loccisano / Getty Images)

One of the bigger surprises of the day is the sight of Anna Nicole Smith's daughter Dannielynn hitting the Derby with her mother's hat. Fans were stunned at the surprise as photos of the young girl alongside father Larry Birkhead spread online. Birkhead shared the photo on Twitter.

"Dannielynn looks pretty in pink in her dress by Junona and her Mom's hat from her unforgettable appearance at The Kentucky Derby in 2004," he wrote.

anna_nicole_smith_daughter-dannielynn
(Photo: Twitter / @larrybirkhead)
prevnext

Even pets get a hat

And just because they likely have no idea what's going on or why today is a special day for their owners, some pets also get the chance to dress up for Derby Day. Harlow the Bunny above is not only sporting the look, but also sporting some winning guidance for who might win the final race.

Then you have the hairless dog below who might not be overjoyed at the moment but certainly maintains a stylish presence despite that.

View this post on Instagram

Who's ready to watch the Kentucky Derby!!! #hairlessdog #dogsofinstagram #kentuckyderby 🏇🏇🏇

A post shared by gremmicorns (@gremmicorns) on

prev
0comments
Start the Conversation

of