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Heading to the derby this year? Let me help you dress the part.

The Kentucky Derby attracts thousands of lucky fans for its prestigious festivities as it does year after year. Attending the Kentucky Derby is not only a fashion forward event but is a must-do destination for many A-list celebrities, movie stars, royal families, the wealthy and more.

The primary rule for both men and women when considering what to wear to the Kentucky Derby and its sister race, the Kentucky Oaks, is to remember that the Derby is not only the most important horse racing event of the year, but it is also a fashion show! That’s why most people who attend the race seriously consider their fashion choices.

Although the Kentucky Derby and the Oaks don’t have an official dress code, there are some unspoken rules depending on where you are sitting in the arena. Derby Day is an opportunity to see and be seen, so if you’re sitting in the reserved areas (grandstand, clubhouse, suites, and corporate hospitality areas), note it is required to be dressed business casual including jackets, suits and collared shirts for men and dresses or pantsuits for women. If you get the chance to sit in the raucous infield that is the place where almost anything goes! Classy but bold is recommended however, even though there are no hard and fast rules, the organizers reserve the right to deny someone entry based on their clothing choices especially if they aren’t dressed up a little nicer, so avoid jeans, tennis shoes, torn clothing, and crop tops.

Now let’s get down to the specifics of what you ladies and gents should wear to the Kentucky Derby and the Oaks should you make your debut!


There are only two options in my mind for women when attending the Kentucky Derby: dresses and pantsuits in sophisticated silhouettes. Colors for these garments should scream Southern Belle for a day or have pastels and solid colors. I know it may seem too much but trust me this truly is the place to have fun with wardrobe choices! I also recommend choosing a dress or pantsuit that is full of color, floral or maybe even something with a horse pattern. Spring should absolutely serve as your inspiration for what you choose to rock at the Derby!

One accessory that must not be looked over are the hats. Wearing a hat to the Kentucky Derby is wildly popular and considered good luck. Really, along with the horses, they are the stars of the event. Most women wear wide-brimmed, Southern Belle type hats, but people certainly get crafty and decorate with flowers, feathers, bows, ribbons, fruit, etc. These hats are especially customizable and allow the wearer to express her creativity and individuality. The tradition of the hat is so essential that each year there are official milliner hats selected at the Kentucky Derby that are showcased in a museum exhibit. From the spectacular to the splendid, there are no rules when it comes to selecting your Derby hat.

As far as your other accessories, just make sure that you have a complete outfit from head to toe. This must include shoes, bags and jewelry, but remember, your hat is the star so don’t feel the need to upstage it.


When it comes to dressing the part for the Kentucky Derby men are certainly not left out of the equation. Much like the women’s wear, being bold is best! Things like bright and pale colors, bold stripes, busy plaids as well as bright pastels will most certainly be front and center. In recent years men have joined the fashion parade at the Kentucky Derby wearing pastel suits and unexpected prints to stand out from the crowd. However, if you want a more toned-down look, or don’t like brighter colors or patterns, a classic seersucker blazer or a navy suit will always be a great alternative.

Starting your outfit by selecting pants first is a good idea because they stand out from a distance. Guys should be daring and select sun drenched colors such as key lime, ocean blue, Bermuda pink and lemon. Any of these colors will look great with the right jacket and a dress shirt in complimentary colors. Don’t be afraid to select a patterned shirt in gingham or a striped shirt since attire is part of the fun and fanfare of the Derby.

Your jacket is what will bring the whole look together and remember you can’t go wrong with a seersucker blazer! As far as two or three button, it’s personal preference. And the tie is the cherry on top of the cake. Have fun with it!  Just make sure it coordinated with your shirt and jacket. This is also a great time for bow ties and if they are your preference, go for it. For shoes, select something classy and clean. Good loafers are recommended, preferably without socks.

For the grand finish don’t forget your hat. Top it off with a fedora or bowler style hat for a true Kentucky Derby look that is sure to impress. No matter what you wear, it’s how you wear it guys. The most important thing is to look and feel good in what you are wearing and to be confident.

Here is a great example of some classy fashion forward looks I helped my client John pick out for the Kentucky Derby this past year. The looks I crafted were timelessly classy and complimented his wife Linda’s outfits perfectly. John went with a more neutral look and added a powdered pink button up, a plaid print bowtie, a darker shoe and of course, the cowboy hat! This outfit had so much attention to detail and incorporates all the fun elements found in Derby wear without it being too loud and in your face. 

Alternatively, this is another outfit I put together for John that has a bit of a bolder look. The fresh pink under the pastel blue coat is super fun and the navy and white shoes and hat are the perfect basic compliments that bring this look together. Whether you choose to rock a bold or more muted look to the Derby you can still incorporate classic elements that will certainly have you on theme.

One last note, if you’re attending the Derby’s sister race, the Oaks, you can wear any color as long as it’s PINK – from hats to handkerchiefs, suits to dresses, sunglasses to heels.  Though there is no hard and fast rule, guests are encouraged to incorporate pink into their attire in an effort to drive national attention to the fight against breast and ovarian cancer.

Feeling happy and confident in what you wear is important for events like the Kentucky Derby and something as simple as your attire can provide longlisting memories. 

I’m Mary from Q. Contrary and I would love to help style you. Feel free to check out my shop in Phoenix at 3168 East Camelback Road or visit my online store QContraryShop.com. I would love to help you find just the right outfit for the Kentucky Derby or even a Derby party that fits and makes you feel good!


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