What to Wear to the Kentucky Derby

Written by Julie Weinstein

Happy Friday! As Carrie mentioned yesterday, the Kentucky Derby is something very near and dear to her heart. And if you’ve never been (or even if you have), finding the right outfits can be quite a feat. You want to make sure to look the part, all while being respectful to the event, comfortable, and, of course, stylish.

While Carrie will share more of her thoughts and experiences on the subject next week, we have a special treat for today’s feature… We decided to turn to an expert in the field of ‘derby dressing,’ someone who has an entire website dedicated to this very thing. Briana Mott runs the website Fashion at the Races, and has even curated her own selection of hats (absolutely gorgeous hats). Briana was kind enough to answer some questions on dressing for the Derby, which should be extremely helpful to anyone who is planning on attending! So, instead of our typical Friday ‘Inspired by’ post, we’re bringing you a ‘what to wear’ post all about how to dress for the Kentucky Derby. Keep on reading…

Interview with Bri Mott of Fashion at the Races

What are the key components to a Derby ensemble?

The most important component of a Derby ensemble is the hat! Racing fashion isn’t racing fashion without millinery. The Kentucky Derby traditions have always included beautiful hats and you really don’t have a Derby outfit without one. In my opinion, your outfit surrounds your headpiece, with a dress to match and then your accessories built off of those two main components. Regardless of which piece you purchase first, your hat is what everyone will look at first.

If it’s someone’s first time attending the Derby, what advice would you give them on putting an appropriate outfit together?

Have fun with it! You will be taking a ton of photos and it really is a day to remember. You will always remember your Derby outfit, whether it is your first or 100th race. Take a look on our website for inspiration, but remember the racetrack is not a night club and a bigger hat does not mean a better hat!

Be sure to not risk comfort if it is your first time at Churchill Downs. You won’t know the terrain and you don’t want to learn it the hard way. Wear heels but make sure you are prepared to be in them all day and to put some miles on!

What are your favorite places to shop for Derby appropriate attire?

I personally love looking at international brands like Keepsake and Rebecca Taylor. True racing fashion can be hard to find in ‘the mall’ because you are piecing together an outfit from head to toe. You aren’t looking for a short summer dress and you aren’t looking for a cocktail party piece either. You are in between the two.

Should dresses be of a certain length? Any “rules” for the silhouette or neckline of the dress? 

I am a huge fan of the midi-lengths. Your dress does not have to be a certain length, but a safe rule to go by is keep it either just above the knee or mid-calf. Maxi dresses either come off as too formal or too casual and anything shorter than two inches above the knee looks like you never changed after the night before.

When it comes to the fabulous hats, is bigger better?

No absolutely not. I actually believe in the opposite. I’ve seen so many woman take their big hats off by the end of the day. They are tired of the weight, not being able to see; they have hat hair and just overall tired of the piece. Find one that will be comfortable to wear all day and still stylish! I am a huge fan of ‘fascinators’ because they can be so chic. Sometimes the bigger hats end up looking cheap only because of all the dressings put on them. Bigger is not better! Just find one that you love and that you’ll love to wear all day.

What’s your personal style when it comes to Derby dressing?

My personal style changes, but I usually like to keep it pretty simple. I try and find a stand out chic dress and work off that. I have a lot of my millinery made to match my dress which helps create the perfect outfit. The shoes and purse are just added benefits to the fashion. I always try to add something new that I normally wouldn’t wear and that just makes it that much more fun putting the ensemble together. Last year, I had pearls in my hat, and then sewed pearls onto my dress for an added detail. It really brought the entire ensemble to the next level.

Since it’s a long and busy couple of days, I imagine comfort is important – what are your tips for a comfortable, yet stylish, outfit?

Just be smart. I do not risk my feet with ‘cheap’ shoes. When I say cheap, it is not so much price, it’s the make. The $20 heels aren’t going to cut it for my 8 hours on track, I pick my shoe carefully and also break them in beforehand. I also come packing with bandaids and inserts just in case. Like I said prior with the hats, I don’t pick anything that I know won’t be comfortable for the entire day. Don’t wear anything that doesn’t fit you. We gals sometimes want to wear a smaller size just because that number seems to matter more than the fit. Don’t do it! No one knows your size and it is more noticeable when someone wears something that doesn’t fit then when they size up! Plus there is a lot of eating and drinking on the day; be comfortable. Sucking it in all day is both exhausting and unnecessary. Be you, be comfortable.

Are certain colors off limits or the more color the better?

I do not like black for the Kentucky Derby. The Derby is a ‘southern belle’ type race. Florals, pastels, happy colors. Leave the black and white or dark colors for Belmont or the fall races. Think spring, ladies!

Any other tips or pointers you’d like to share?

The horse races, and of course the Derby, are all about fashion, fun, and horses! Have fun with your outfit. Plan early, and select carefully. There are lots of photos and memories to be had in that ensemble.  If you don’t have to, don’t skimp on your hat. You don’t need to spend a lot for an amazing piece, but the cheap pieces from your department stores aren’t anything special and you and 100 other girls could be wearing the same one. Find one that defines your personality and your style…and rock it! See you at the races! xoxo

Dresses and Hats We Love

As we mentioned, we highly suggest browsing Bri’s site for a well curated assortment of hats. In addition, below you’ll find a number of dresses and hats that would be absolutely perfect for the Kentucky Derby, so keep on scrolling.

Inspiration from Last Year’s Derby




In Closing

Finally, in closing, a huge thank you to Briana for her wonderful insight on dressing for the races! Are you heading to the derby this year? If so, what are you planning on wearing? Do let us know in the comments below; we’d absolutely love to hear! Have a great day, and be sure to check back this afternoon for the Weekend Edition.

Photos courtesy of Joe Lyman


    1. Thank y’all so much for sharing!

  1. Sarah says:

    Kentucky Derby is like a beautiful integration of race course and tons of fashion lovers. I liked the way you carried it so elegantly. Also nice writing style. Thanks, dear for the blog.

  2. Sara Lannon says:

    Where did you get your beautiful hot pink/blue floral dress you are featured in for the derby? I’m obsessed with it❤️

    1. Hi Sara – it’s from Sachin & Babi. Thank you. 🙂

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