The Kentucky Derby is the bucket list event that I didn’t know I needed. I’ve been to Derby parties in years past but had never thought I’d get the chance to spend a weekend at the most prestigious horserace in the US. The 145th Kentucky was one for the books – and a historic one at that! Walking into the weekend, I wasn’t 100% aware of all the traditions that surround the horserace but I definitely left with an appreciation of the sport!
For Kentucky Oaks, I sported all pink as the day is dedicated to female-only races for the horses. Instead of a rose prize like the Derby, the fillies are racing for lilies! Linen saved my life at the Derby. I wore a Linen Guana Floral Blazer which featured a fun and bold flower print and paired it with Vineyard Vines’ “Lobster Pink’ Stretch Breaker Pants. Made specifically for the Kentucky Oaks, the pink Lily Cocktail Tie was perfect to pull my look together! I had a pair of blue topsiders that also worked perfectly for this outfit as it matched the flowers on the blazer.
Shop my Kentucky Oaks outfit here:
As for Derby day, I wore one of my favorite looks to date! I also remembered that I love seersucker. It’s such a light and breathable fabric – I need to get more seersucker! I was hooked on the Vineyard Vines’ Parade of Horses Blazer and after going to the Derby I love it even more as it’s such a great representation of the people at the Derby! A pair of seersucker pants and topped with a straw hat (can’t forget the bowtie!) and the look was Derby perfection.
Shop my Kentucky Derby outfit here:
Tips for the Kentucky Derby:
- Bring your brightest pastels and loudest prints.
- Kentucky Oaks is Friday, the day before the Derby. Be sure to rock pink!
- Study the horses – I’m not good with stats and numbers, but get friendly and talk to those around to see who they’re betting on and why!
- The Mint Juleps weren’t really that great. Out of all places ~ THIS should be the go-to for a mint julep! Instead, go for a Spire: Woodford Reserve, Lemonade, Cranberry. It was so refreshing and easy to drink!
- Wear comfortable shoes – it’s going to be a long day
- Sunglasses (or a poncho if it might rain)
We didn’t get to explore the city of Louisville extensively as the Derby took up most of my time there, but I compiled a few of my favorite spots in Louisville:
- Proof on Main – located at the base of the art-forward 21c Hotel, Proof is an eclectic restaurant with elevated comfort food and also boasts amazing cocktails (I got the Kingslayer!)
- Against the Grain Brewery – The wings are insane!
- Royals Hot Chicken – some of the best fried chicken I’ve had — move over KFC!
- Butchertown Grocery
- Odeon – a beautiful and comfy mid-century designed cocktail lounge
- Pin + Proof – Located in the Omni Hotel, this speakeasy boasts a bowling alley and great cocktails
Have you been to the Kentucky Derby or Louisville, Kentucky? It was one heck of a weekend and an experience that I’m not forgetting any time soon. Thanks so much to Vineyard Vines for having me!!
Stay Risky,
– John
Photography by: Demi Ward
