What to wear to the Kentucky Derby with Indigo & Cotton and IW Harper

Kentucky derby

What is the fastest two minutes in sports? The Kentucky Derby of course. On May 7th men and women from around the world gather in Louisville to drink, bet and gawk. Whether you are watching the derby from the bleachers of Churchill Downs or at a local bar, you want to look as sharp as a tack while drinking your julep.


We asked Brett Carron from Charleston’s menswear shop, Indigo & Cotton for some tips to make sure you look like a style stallion and not a show pony.



The Hill-Side – Primarily known for their ties and pocket squares made up in unique Japanese fabrics, the brand has recently broadened their offering to include apparel, bags and hats such as this woven Panama style.



Barena – A linen jacket that is casual but elegant, and quintessentially Italian.  A win-win for looking sharp and staying cool this season.



Gitman Bros. Vintage – One of the few remaining American shirt-makers, they have a rich history and arguably the best fitting button downs.  This linen stripe version is our favorite this season.



orSlow – A recent addition to our lineup out of Japan specializing in meticulously crafted wardrobe essentials. White denim is the perfect choice for spring and will keep the rest of the outfit looking fresh and new.



Billykirk – Formed by two brothers with the idea of making classic, high quality leather goods built to last.  This slim belt can easily be dressed up or down depending on the occasion.



Shuron – Made in Greenville, South Carolina with over 150 years of experience making glasses. Our go-to for timeless frames.

We can’t cover the Derby without discussing bourbon. The good fellas at I.W. Harper sent us these two recipes. Give them a whirl and share them on Instagram. Be sure to tag us.

Vinceremos Julep


Courtesy of Marie Zahn, Hawthorn Beverage Group

1.25 oz. I.W. Harper Kentucky Straight Bourbon Whiskey

.75 oz. Amontillado Sherry

One tsp. Ginger Syrup

Eight mint leaves and three fresh mint sprigs

Glassware: Julep Tin

Instructions: Lightly muddle mint and ginger syrup, add other ingredients and top with pebble/crushed ice. Swizzle briefly and top with more ice. Garnish with three mint sprigs and straw.

Harper’s Bet


Courtesy of Mark Corley, The Silver Dollar

1.5 oz. I.W. Harper Kentucky Straight Bourbon Whiskey

.5 oz. Grenadine

.5 oz. Lemon juice

.5 oz. Grapefruit juice

3 dashes Orange bitters

Instructions: Shake and Strain over fresh ice in an old fashioned glass. Garnish with a lemon wheel.

Image credit: Brenda Kean/123rf.com

We are working with I.W. Harper but all opinions are ours.