20 Gorgeous Photos from the best Kentucky Derby Party in Chicago

Kentucky derby viewing party

What to Wear to a Kentucky Derby Party

Dress by Jack Mulqueen| (similar) Alyx Sleeveless Polka Dot Sheath Dress • jcpenney • $29.99

Hat from HooDoo Headwear in Oak Park| Call for details 708.383.4466

Shoes by Aldo| (similar) Fendi nude bird print leather heel sandals • Fendi • $715Shoes of Prey Block Heel Leather Pump (Women) • $188.95
Kentucky derby viewing party

With the weather almost reaching 80, it was a perfect day for I|O Urban Roofscape’s 2nd annual Kentucky Derby Day Party at the Godfrey Hotel. The roof was packed with mint julep drinkers decorated in their Sunday best. Big brim hats eclipsed painted eyes, gingham suits paraded from one end to the other, and bright red lips painted the unending supply of martini glasses held high by equally dapper bartenders. The scene was classy and charmingly inviting.

Confession: I have no idea what the derby even actually is. It involves horses. I know that. Primarily, though, I believe it’s about hats. Obnoxiously grandiose, unbelievably gorgeous hats. Basically, it’s a hat show – with horses. Also, martinis.

Since I’m embarrassingly ill-equipped in the headwear department (I own exactly one hat. It’s this one. This one isn’t mine. I stole it from a cop.), I headed down to my neighborhood mad hatter for a derby ready topper. If you’re in the Oak Park area, I highly recommend HooDoo Headwear. Their staff was friendly, extremely helpful, and their prices are competitive. Hats are expensive so I wanted one I could wear to multiple events and with a few different colors. They selected for me a beautiful wide brim neutral raffia hat, handmade in Madagascar, and I made it work with a vintage silk orange polka dot dress I scored from a thrift store back in high school.

This year’s Kentucky Derby party at I|O, which lasted from noon until 8 p.m., proved to be the perfect way to spend a warm spring day in Chicago.

Enough chatter. Here are the hats!

Kentucky derby viewing party

Godfrey Hotel Rooftop

What to Wear to a Kentucky Derby Party

What to Wear to a Kentucky Derby Party

Kentucky derby viewing party

What to Wear to a Kentucky Derby Party

Godfrey Hotel Rooftop

What to Wear to a Kentucky Derby Party

What to Wear to a Kentucky Derby Party

What to Wear to a Kentucky Derby Party

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

Godfrey Hotel Rooftop

What to Wear to a Kentucky Derby Party

 

DurrrBaaaay Life! #kentuckyderby 🐴 🐴 🏇 🏇 🎩 👒👚👠👜 🍸

A photo posted by Kari, Editor of Chicagoings (@chicagoings) on