Kentucky Derby Dresses for Women: Printed Midis, Pastel Maxis and Derby Day Outfits

Derby is the one day a year when American women dress properly for a daytime event outdoors, and the only real risk is being underdressed. These are printed midis, pastel maxis and jackets designed for exactly that — by me, Sandhya Garg, Project Runway season 13, previously at Alexander McQueen, Gucci and Liberty London. Every print is one I drew myself.

The next Kentucky Derby is Saturday, May 1, 2027 — the 153rd running, with the Longines Kentucky Oaks the day before on Friday, April 30, per Churchill Downs. If you are going to both days, you need two outfits, and the Oaks one can be the brighter of the two.

What the actual dress code is

Churchill Downs publishes its own guide to what to wear, and it is worth reading before you buy anything. Three things from it matter more than any trend:

"There are no hard and fast rules when it comes to Derby dressing." There is no required hemline and no required colour. What there is, in their words, is a dress code encouraging upscale attire.

"The higher up you go in the clubhouse, the dressier the attire." This is the single most useful line on their site and almost nobody repeats it. Where your seat is decides how formal your dress should be. A box in the clubhouse is a different brief from a spot in the infield. Check your own ticket before you choose.

"An uncomfortable shoe will ruin your day." Derby is eight to ten hours, much of it standing, much of it on grass. They recommend packing a second pair to change into. Take that seriously — and choose your hem with your heel height in mind, because a maxi cut for heels drags on turf in flats.

About the hats — I don't make them, and here's how to buy one

Churchill Downs puts it plainly: "You can't come to Derby without a hat or fascinator." I design dresses and jackets, not millinery, so I am not going to sell you one. What I can tell you is how to get the pairing right, because this is where most Derby outfits go wrong.

Buy the dress first, then the hat. A hat is easier to match to a dress than a dress is to a hat, and a good milliner will work to your fabric.

Pick one of the two to be loud. A wide, heavily trimmed hat wants a quieter dress under it. A large-scale print like mine wants a simpler hat that picks up one colour from the print rather than competing with all of them.

Match a colour, don't match the whole thing. Matching hat and dress exactly reads costume. Pull one shade out of the print and let the hat be that.

On what is current: TODAY reported from the 2026 Derby that stylists are pointing people toward pillbox hats, closed-toe shoes and top-handle bags, with the advice to "channel Jackie O in her elegant, lady-like accessories." A pillbox is also the easiest hat to wear for ten hours, which is the real argument for it.

The dresses

The classic Derby answer is a printed midi. Knee to mid-calf, a print you can see from across a lawn, a sleeve or a strap that works in sun. Noor ($278) in pink and yellow with a scalloped front seam, Sophie ($255) in green with bell sleeves, Louis ($238) as a printed halter, Queen ($258) in pink and purple, and Casablanca ($298) in hot pink pinstripe.

Pastels, if you want the traditional look. Kamal ($228) in light pink jacquard, Marie ($278) with floral embroidery, Versailles ($258) as a pink printed shirt dress, and the pink square-neck fit-and-flare maxi ($298).

Or go properly bright, which photographs better in full sun and is what the infield and the paddock actually look like. Yellow fit-and-flare maxi ($298), Gatsby in tangerine ($298), Antonia in green ($285), Carolina in pink with a balloon sleeve ($265), Marquis in royal blue with embroidery ($328), Duchess in red ($298) and Jharokha in rust orange ($298).

Florals that aren't the usual floral. Azalea ($235), Freesia ($225) and Blossom ($207), all cotton wraps you can sit down in.

Bring a jacket. Louisville in early May is not warm.

This is the part people get wrong every year. The first Saturday in May can be seventy-five and sunny or fifty-two and raining, and the race goes ahead either way. A shawl blows about; a structured jacket photographs well and stays put.

The Agra gold jacquard jacket with velvet bows ($228) and the Klimt lace blazer ($255) both dress an outfit up rather than muffling it. The Diana floral ($358), Emma green ($338) and Arte velvet ($198) do the same job. More in one-of-a-kind jackets.

For what you carry: a printed cotton tote holds the flat shoes, the programme and the phone, which a small bag will not.

Browse by colour and length

By colour: pink, yellow and green dresses. By length: midi and maxi. By style: floral, A-line and shirt dresses, or the plus size occasion range. Related occasions: garden party, wedding guest and special occasion dresses.

Read more: my longer guide to what to wear to the Kentucky Derby, every wedding dress code explained, and how to care for embroidered pieces.

Sizes XS through 3XL. Check the size chart first. Free US shipping over $250. Afterpay available. Ships from Scottsdale, AZ within 1–3 business days.

Questions I get asked

What should a woman wear to the Kentucky Derby?

A dress in a strong colour or print, knee length to maxi, with a hat or fascinator and shoes you can stand in for ten hours. Churchill Downs says there are no hard and fast rules but encourages upscale attire, and that the higher up you sit in the clubhouse, the dressier it gets. Bring a jacket: early May in Louisville is unpredictable.

When is the next Kentucky Derby?

Saturday, May 1, 2027 at Churchill Downs in Louisville — the 153rd running. The Longines Kentucky Oaks runs the day before, on Friday, April 30, 2027. The Derby is always the first Saturday in May, so if you are shopping a year ahead you can count on that.

How long should a Derby dress be?

Anything from knee length to floor, and the choice should follow your shoe. A midi is the safest and most common answer because it works with a block heel on grass. If you want a maxi, make sure the hem works with the shoes you will actually wear, not with heels you will swap out by three o'clock.

Do you have to wear a hat to the Kentucky Derby?

Effectively yes. Churchill Downs says you can't come to Derby without a hat or fascinator, and in the clubhouse you will be conspicuous without one. A fascinator is the lighter option and a pillbox the most comfortable over a full day. I make the dress, not the hat — buy the dress first and match the hat to one colour in the print.

What colours are best for the Kentucky Derby?

Anything except black and anything too close to it. Pastels are the convention and bright saturated colour is the modern answer; both photograph well in full sun, which is what Derby photographs are. Prints hold up better than solids over a long day because they hide creasing.

What is the difference between Oaks day and Derby day dressing?

Oaks, on the Friday, is slightly less formal and the crowd is smaller, so it is the day to wear the louder of your two outfits. Derby Saturday is the dressier of the pair. If you are attending both, buy one printed midi and one maxi rather than two of the same thing.

Can I wear a jumpsuit or trousers to the Derby?

Yes — the dress code is about being dressed up, not about wearing a dress. Tailored wide-leg trousers with a jacket read perfectly well in the clubhouse. I would still take the hat seriously whichever you choose, because that is the part people notice.

How far ahead should I order?

Six to eight weeks, which leaves time for an exchange if the size is not right. Derby styles sell through in March and April every year, so January and February are the comfortable months to decide.