Kentucky Derby Style & Advice

By John Clifford

The Dapper Fit

Growing up in Louisville, Kentucky the Derby signaled that spring was here, and the mint juleps were ready to be shared. Every morning the papers would cover the race predictions and help us pick a winner. With our picks in, it was time to start picking out the Derby outfit. In general Kentuckians are casual dressers. Visiting exclusive boutiques or buying bespoke were out of the question for locals. Aside from a few local shops who offered  made to measure, the department store held the key to our tailoring. With excitement we would grab our trusty department store blazer, khakis, dress shirt (usually white, but sometimes pink or patterned), and if you really wanted to be fancy a bowtie. All so we could gather with family and friends at the yearly “Derby Party” to drink mint juleps and bet on the horses. 

As someone who grew up in Louisville and fell in love with tailoring later in life. I find great joy in helping you create the best outfit possible for my beloved race. The purpose of this article is to talk about what to wear to the derby if you want to be considered among the well dressed. I’ve shared above that I would not have considered myself well dressed on many Derby days in the past. So in the spirit of learning and becoming the best version of ourselves, let's first think about the principles of Derby outfits. These can be applied no matter what color your outfit is, or if you even have a sport coat in your closet to begin with. 

Principles of Derby Style

The Derby is a celebration of spring. Every year the winner of the race is adorned by a garland of fresh cut roses. With the spring colors on full display you should opt for pastels in your outfit. Namely light blue, mint green, soft yellow, lavender, and of course light pink. While we respect the confidence of a monochrome look, we suggest working these colors into your outfit more subtly. A light blue tie, or pastel colored shirt underneath your jacket will ensure you are in the spirit without going over the top. In life discretion over showmanship is almost always the better way to go. Our second principle runs counter to what we just talked about, but let me explain. Wearing one bold item is not just expected at the Derby, it’s almost encouraged. Keeping in good taste is all about how it’s done. For example boldly patterned sport coats can be seen on display all over the paddock. If that’s what you choose to wear then simply tone down the rest of your outfit so as not to overpower the viewer. A quick note on hats, they are a big deal at the Derb. If you choose to wear a hat opt for a summertime straw hat. You can’t go wrong with either a boater or fedora. We say go for it, have fun, and be that best version of yourself. Just don’t be surprised if you are outmatched by the hats worn by the fairer sex.

What to Wear: Two Winning Looks

Now for the fun part. Let’s dive into the outfits we recommend for the Derby. As a set of ground rules we will be tailoring our suggestions to the average guy who doesn’t necessarily have an extensive wardrobe. Don’t worry we were once beginners ourselves, and let’s be honest. The menswear enthusiast is going to do their own thing anyway. The first outfit will be based off a menswear staple in nearly every man's closet. Which is the classic navy suit. Our second selection is less common but still quite useful across many situations and worth considering if you don’t already have one. The patterned sport coat. 

The navy suit is the perfect blank canvas for us to construct our first masterpiece. We want a fabric that will keep you cool on those hot May days in the south. The most universally accessible choice is lightweight wool, but bonus points if you own a navy suit in cotton, linen, or seersucker. Avoid wearing a heavy wool flannel suit at all costs. Starting with the footwear it pays to keep in mind the rule of thumb that you want your shoes to be darker than your pants. Which is why we suggest dark brown shoes. At the Derby you can pull off many different shoe styles. So we chose to have a little fun and go with wingtips for our outfit. When considering the shirt light blue is always a safe choice and it would fit into our spring color scheme, there's no shame in that choice. We decided to go with a subtle blue striped spread collar dress shirt, but you would be well within your rights to wear a pastel pink or yellow shirt. When choosing the tie we want to compliment the colors in the outfit. An orange tie with a nice light blue floral pattern does that and fits the bill. Consult the color wheel included if you are as clueless about complimentary colors as we were. Since most ties do have a pattern and secondary color opt for something you can easily compliment your pocket square with. Speaking of which, any derby outfit would not be complete without a pocket square. A light blue paisley in this situation will perfectly pair with the orange tie and light blue floral pattern. Remember it’s good taste to have the pocket square compliment the tie, not match it exactly. The same principles apply across the entire color spectrum of the outfit. Now, throw on your straw fedora and head out dressed well from head to toe.

There’s something about a handsomely patterned sport coat that just makes you stand a little taller. For our second outfit we chose one with a grey base, and light blue and brown checks. Let’s start from the bottom of the outfit again and remember the rule of thumb that the shoes should be darker than the pants. Since we will be wearing khaki trousers it opens up many different color options. In that vein we opted for a medium brown pair of monk straps. Now the more casual nature of the sport coat allows us to play with different shirt collars, and that’s why we chose the Oxford cloth button down. In order to avoid clashing with the pattern on the jacket a plain white one will fit the bill. Now for the pop of spring color this outfit has been waiting for we will be wearing a light blue repp stripe tie. As always we need to make sure the pocket square compliments the tie and thus we chose a rust orange pocket square. Finishing off with some brown wayfarer sunglasses is the garnish on a perfectly crafted outfit.

We wouldn’t be a menswear resource if we didn’t briefly mention the elephant in the room. That being the classic southern suiting staple. The white seersucker suit with light blue stripes. You will almost certainly see these suits on Derby day, and not just in your traditional light blue stripe. If you own one by all means wear it! I personally used to own a seersucker blazer that I wore all the time. This article is meant as a starting point for your derby outfit design. The same applies to the tan cotton suit which you can see I wore to the Derby a few years back. If you love this stuff like we do and have the wardrobe to accommodate outfits of this nature we would be upset if you didn’t wear them and celebrate Kentucky’s biggest day in style. 

Final Thoughts

In conclusion the Derby is an atmosphere of fun. Remember the key principles we have laid out in this article. Wear your spring colors and don’t be afraid to be bold. As long as it is done tastefully and within reason your Derby outfit will make you feel like the best version of yourself. Stay Dapper Out There.