Last Updated on April 29, 2025 by Eve Dawes
Kentucky Derby shoes need a bit of planning these are the prettiest around!
Kentucky Derby shoes for women are just as essential as the outfit and hat but often get overlooked. After years of attending different races there’s a few things I’ve learned and am going to share. So that you don’t have to sacrifice fashion for function. A bad pair of shoes can totally ruin an otherwise fabulous outfit and the Kentucky Derby is all about the fashion. Well, second to the races anyway. So if you’re in need of some help finding your perfect pair of ladies Kentucky Derby shoes. As well as some tips for staying comfortable and upright (I can’t help you if you’ve had too many Juleps), keep reading.
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Amongst all the pageantry and fanfare of the occasion, one thing is for certain: The show-stopping fashion of the Kentucky Derby is like nothing else on earth!
Kentucky Derby
Can I wear heels to the Kentucky Derby
A lot of people will say no and to stay away from stilettos or pointy heels for any kind of horse races, events on grass or for women’s Kentucky Derby shoes. I say it depends on your comfort level, experience in heels and which area you’re going to be seated in. If you look at this photo it’s not just me in stiletto heels (ignore the rest of the outfit, this photo is from 2015!). A lot of the other women around me are wearing them too.
If you’re planning on walking on the grass a lot and it’s looking like the ground will be soft probably not. If the ground’s hard and you’re in a box or going to be sat most of the time you’ll probably be fine.
Having been a ballerina and being used to dancing in pointe shoes or heels, walking in regular heels is second nature so I’ve never had an issue wearing heels to the races. Watch me face plant next time now that I’ve said that. However, I’ve also never gone on a rainy day. I probably just jinxed myself there.
So yes, you can wear stilettos for your Kentucky Derby shoes but that doesn’t mean you should. Only you can decide. There are so many other stylish options you can wear instead. I’m now converted to spool heels after wearing them to the races last season. As well as wedges, at least for now anyway. My recommendation is to wear the pair you feel the best in and can walk in. Then take a pair of fold up flats with you.
Take fold up flats if you’re wearing heels
That way you can look fabulous from head to toe in all of your photos but there’s no shame in changing into fold up flats to walk around or to and from the car park. Just make sure they fold up small enough to fit in your purse that meets the size requirement. If it’s wet or damp underfoot you might want to take a small plastic bag to put your shoes into before putting them back in your bag.
The best alternatives to stiletto heels for ladies Kentucky Derby shoes
If you’re worried about stilettos being impractical to wear to the Kentucky Derby, these are great alternatives for women’s Derby shoe choices:
- Wedges
- Espadrilles
- Sculptural heels
- Spool AKA pyramid heels
- Chunky platform heels
- Block heels
- Kitten heels
- Slide sandals
- Ballet flats
- Loafers
When it comes to deciding on which Kentucky Derby heel or flat is right for you consider your outfit as a whole. A more formal style is going to look better with sculptural, spool heels or wedges than with espadrilles or flats.
What horse racing shoes are in fashion this year
Expect to see lots of slingback heels, ballet flats, espadrilles, sculptural heels and wedges which are all major shoe trends this summer. The enclosure you’re in and the weather will help to determine which is best for you. If it’s wet and you’re going to be doing a lot of walking and standing on grass maybe stay away from stiletto heels.
If you’re pretty much car to table, it’s dry and you’re staying on concrete you can pretty much wear anything. I tend to always pack a couple of pairs and choose on the day which one I’m going to wear based on the weather.
Shop the best Kentucky Derby Shoes for women
These are the most stunning shoes to complete your Kentucky Derby outfit. From pretty ballet flats to unique wedges and the prettiest heels for whatever you feel will work best for you. If you go for stiletto heels but are on the fence about them, don’t forget your fold up flats! Whichever style you choose, remember to try and break them in first and if there’s any areas that might rub to pack some bandaids.
Be careful if you go for satin or suede ladies Kentucky Derby shoes and make sure to use stain protector in them in advance. I recommend leather over any other material.
Don’t forget the bag
No outfit is complete without the perfect bag. Whether you’re headed to Churchill Downs or just dressing the part, don’t forget a handbag in a pretty spring shade to compliment your outfit perfectly. A winning look is all about the head to toe details. If you don’t want to splurge on a color or style you wouldn’t normally wear, consider renting from somewhere like Switch. It’s where I rent a lot of my designer bags from. Use code DawesEve22J at checkout for $50 purchase credit. Just be sure to check the bag rules and dimensions for the ticked area you’re in.
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