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Kentucky Derby Fashion | Yeas and Neighs

Kentucky Derby Fashion | Yeas and Neighs
Katharine Clark

The Kentucky Derby is known as a horse race, but also for its particular fashion style. These days, race day has its own red-carpet receiving line for all the celebrities and socialites that attend. Overall, the look is summertime dressed-up whimsy. Even if you’re not attending the race itself, getting the derby look right is key. We’ve compiled a list of Kentucky Derby Fashion Dos and Don’ts (Yeas and Neighs) to help you.

Women’s Style

Perhaps most iconic about the Kentucky Derby is the menagerie of glamorous, outrageous, whimsical but mostly large head-wear that adorn the women who attend. Bigger than church lady hats, more unusual than hats worn by duchesses at royal weddings, and even more outrageous than Aretha Franklin’s concert headwear, the hats at the derby deservedly have their own contest.


Women’s Hat Yeas and Neighs


  • DO make hats structural, abstract and elegant like art; Fascinators (smaller, headband decoration) look best when they are whimsical and not over-accessorized.
  • DO coordinate your hat with your outfit.
  • Do understand that bigger brimmed hats can make you appear thinner. Flatter hats can make you look wider and shorter.
  • DO understand that feathers can be elegant accessories in moderation.
  • Do vary your embellishments, strike for a balance of whimsy and taste.


  • DON’T use figurines; literal interpretations tend to look like you raided objects from a mini-golf course.
  • DON’T go matchy-matchy with your outfit like I did in 5th grade. Even my neon headbands matched my neon socks and nail polish. *shudder*
  • DON’T hide behind your hat, or make it so big someone might trip on it or assign it RV parking.
  • DON’T go overboard with feathers making you look like a star of Fraggle Rock.
  • DON’T go overboard with sequins, or other embellishments, or you may be asked to MC the local drag show. Full on sequins are completely appropriate if you plan to WERK, but not at the derby.

Women’s Outfit Yeas and Neighs


  • If in doubt, DO wear a pretty, age-appropriate, summer fabric dress; think daytime summer wedding.
  • DO wear classic patterns, like polka dots or florals, and ruffles and tulle are ok if understated. Tulle and ruffles can look rather ballerina or “labial” if too much and no one wants to look like lady-bits.
  • DO wear pants if they are well tailored flowy slightly palazzos with a heel. The fabric here is key: Too light of Linen wrinkles, anything shiny is a horror show. Tread carefully, you can easily begin to look like a badly dressed mother-of-the-bride. Avoid this with more feminine heels (e.g.big chunky heels and pants is a too-casual don’t).
  • DO wear comfortable shoes but they must be elegant and in seasonal colors and shapes (black is okay if you’re wearing black or other dark colors); neutral or pastel sandals are a good option; I will remind you all that muted gold, or silver are a neutrals. Little strappy 1.5″ high wedges are a good, comfortable choice.


  • DON’T wear something shiny, or skimpy, too casual or too cocktail. Don’t wear a pink searsucker 70s jumpsuit with ruffles and camel toe. (I’m talking to you, Bethany Frankel).
  • DON’T wear all one fabric head to toe. Seriously, no.
  • DON’T wear excessively tight, short or shiny pants; they are not appropriate.
  • DON’T wear cowboy boots even if they are bright and ‘cute’. No, silence, just don’t.
  • Denim is not a good idea. It’s not quite a DON’T as I can see very very fancy wide leg pants with heels working, but this is just best avoided.

The gold standard outfit for women at The Derby is:

  • a pretty summer dress in silk or other light fabric which is overall simple but with an interesting detail.
  • a structural straw hat with pretty floral, ribbon and feather details that is not the exact same color, but coordinates with the dress.
  • an understated but elegant pair of shoes that are comfortable enough to stand and watch the race
  • an elegant but daytime bag and accessories.

Men’s Style

Again, for men, the Derby is summertime dressed-up whimsy. We might even call it whimsical dapper. Outfits tend to be lighter weight fabrics like linen, seersucker and cotton in lighter colors. Pastels in shirts and ties, and even in patterned suits are common. The key is to look dapper and ties, vests, jackets, kerchiefs, bow-ties and other formal attire is a must. The outfit should be playful and accessorized with straw hats, bright bow-ties, and impeccably mismatched patterns. If you look like you’re going to a nightclub or board meeting, you’re wearing the wrong outfit.


Men’s Outfit Yeas and Neighs


  • DO wear summer weight fabrics, in lighter, or brighter colors. They MUST be crisp and tailored correctly.
  • DO wear a pressed well-fitting seersucker suit either as a full suit or as pants and/or jacket separately. There’s a contest for ‘Best Seerksucker’ at the Derby and it’s iconic summer southern wear.
  • DO mix and match patterns if they share the same color palette.
  • DO wear a crisp summer weight hat and keep your accessories limited.
  • DO coordinate with your date’s outfit.


  • DON’T wear boring dark suits with black shoes. You want to stand out a bit, not go to an interview.
  • DON’T wear rumpled or ill-fitting seersucker (I know, it’s hard) and don’t wear it with black or dark brown shoes unless the seersucker color is itself black or dark grey.
  • DON’T make everything a pattern. If your suit is patterned, only contrast the tie, or kerchief. You risk giving everyone seizures with too many patterns.
  • DON’T go costumey. Having too many accessories can easily make you look like an extra in the local community theater’s revival of ‘Annie’.
  • DON’T look un-groomed. Why bother wearing something crisp if you look unkempt?

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  1. Danny King

    I have to disagree. That vision in dark lavender with the human size fruit roll up on her head is a vision of sophistication. She’s invited to any party I throw as long as she can fit in the door.

    • Danny King

      By my repeated use of vision. I’m clearly a few drinks into the race ;p

  2. Michelle

    Can men wear jeans at a more casual costume party fundraiser?

  3. Katharine,

    I appreciate your post & perspective on Derby DO’s and DON’Ts. Have you thought about maybe changing your layout a little? Reading your DO’s and DON’Ts on the hats and outfits had me a little confused with them being all together. Maybe separate the DO’s and include photos with those, and then include DON’Ts and photos in their own list area. Having common information and photos together really makes it easier for your audience to connect, rather than having to bounce back and forth between DO & DON’T. Also, have you thought about maybe attaching links to items that ARE Derby DO’s? I see that you included “CHECK OUT MORE OF OUR DO AND DON’T LOOKS ON PINTEREST,” but maybe have photos/links that entice your reader to click on them thru your account.

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