If a world-class horse racing event is not intriguing enough, what about a spring fashion show where everyone is bringing their A-game with all kinds of extravagant dresses, vibrant hues 🌸, and statement hats? 👒
Yes, you guessed it, I’m saying the Kentucky Derby Festival.🏇✨
From celebrities to fashion bloggers, the Kentucky Derby is such a visual enjoyment that is full of all kinds of crowds.🎉
If you are struggling with what to wear for this big day, trust me you are not alone.
🥹🥹🥹🫶
That said, I’ve come up with 15 Kentucky Derby outfits in different styles from casual to dressy.
For the plus-size base, stay tuned for the styling tips!
Enjoy ladies! 💕
Oh, and I also included a short clip demonstrate how to roll up jeans elegantly further down the blog post, make sure you grab this styling tip — enjoy my loves!❤️
1. Stay elegant for Kentucky Derby❤️👇🏼
When it comes to classic derby party attire, it’s about looking all poised and elegant with a dash of fun.💃🌟
That said, you don’t want to be too revealing with hot pants.
That just looks like you are trying too hard in the wrong way.
Staying classy with a high-quality, structured midi skirt is always a failproof way to go.
Of course, there are no fast and hard rules about it.
Dresses that are over the knee can be acceptable as well, depending on your overall look.✨👜
If you want to add a dash of femininity with a posh look, an off-shoulder dress is such a winning option of all time. ✨
Together with close-toe heels and a dainty clutch, you just look effortlessly dazzling. 🌺
Below is one of my favorites.
Need I say more? So elegant!
2. KEEP IT CASUAL WITH A JUMPSUIT ❤️👇🏼
Can you wear casual wear like jumpsuits for the Derby party?
Well, the time has changed, and the traditional ladylike, elegant look is no longer the only option these days.
For a youthful look, team the vibrant floral co-ord set with a wide-brimmed straw hat and espadrilles wedges just scream the delightful springy vibes. 👒💓
However, if you want to add a dash of a cool attitude, perhaps it’s time to consider a sleeveless blazer jumpsuit.
Featuring a structured collar and thick fabric, it just brings out distinctive vibes compared to ordinary slouchy jumpsuits.
Want to spoil yourself with a fun girl boss look?
Check this look from gorgeous Nicole below!✨
With the high waist and flared pants design, it just flatters your body to another level.👖💕
Reminder: Walk heel-to-toe, not toe-to-heel!
Since there’s a good chance you’ll be rocking high heels that day (especially with your flamboyant dress), I thought it might be helpful to share a basic yet crucial reminder: Walk heel-to-toe, not toe-to-heel!
One of the quickest ways to look awkward in heels is to plant your whole foot flat on the ground like you’re wearing sneakers.
Instead, step with your heel first, then roll onto your toe.
This little trick will make your stride look smoother and more natural. Plus, this is way more effortless to walk in this way <3
3. KENTUCKY DERBY LOOK FOR COLD WEATHER❤️👇🏼
As we all know, the Kentucky Derby is an outdoor event and the weather can be pretty unpredictable sometimes.☁️❄️
If that day is more on the chilly side, it’s time for you to dust out your statement coat.🧥✨
As such, an expensive-looking faux fur trim coat or a Chanel-style tweed suit would be ideal.💎
To glam up the look, I would suggest you wear the gloves as a set!🧤💕
As a petite girl, I am in love with Georgia Toffolo’s style.💖
Styling a white turtleneck with cream pants and belt it up with a sleek tweed jacket on top? PERFECT.🌟
Thanks and I’ll just copy this look!
When the days are chilly out, a white puffy-sleeve sweater dress just looks so aesthetic.☁️
And also, throw on a blazer when in doubt!
Another tip to make wearing heels more comfortable: Heel cushions
They help to absorb the impact and prevent friction at the back of your heels.❤️
When you wear them, they create a protective barrier between your heels and the shoes, which reduces strain and friction.
So, using heel cushions can make wearing high heels for a long time less painful and irritating.❤️ Hope that helps!
More winter Kentucky Derby outfits below as these outfits are absolutely STUNNING – save this for later reference <3
This color combo is just so classy.
Loving this monochrome fit with all shades of beige!
4. TOP IT OFF WITH A PERFECT HAT ❤️👇🏼
If there’s one thing that makes the Kentucky Derby so one-of-a-kind compared to other fashion events, it’s the honorable hat tradition.🎩✨
So ladies, repeat after me, ” I WILL BRING MY A-GAME AND FIND AN EXTRAORDINARY HAT“📣
Okay, you probably ignore it, but seriously, my point is to be as dramatic and wild as you want.🦚💖
Trust me, people certainly pay more attention to your hat than your dress.
Among all kinds of hats, I will always suggest wearing a big statement hat with pastel hues for a sure-to-turn-head look.👒
But if you want to keep things subtle, fascinators can be a really good choice for a dainty look.🌿✨
Plus, they are definitely easier to carry around!
By the way, if you have chubby cheeks like me, another quick tip is to always wear the hat aside.💖
It just opens up your face more and contours your face to be smaller!
Disclaimer about sharing styling tips & inclusivity:
The truth is, we are all perfect imperfections. 💕
You want to learn these outfit hacks ONLY if you feel like it but are not pressured by others. Remember, we never have the need to “fix” our bodies!
You don’t have to be pretty like HER, you can be pretty like YOU.
While researching this article, I just realized there’s still not enough plus-size and black women’s fashion content for the Kentucky Derby event.
I tried to update this article with more different types of ladies (if I can find it) – and hopefully, that makes us aware of inclusivity.
So dear, if you found this content helpful, please help pin the pin below & support♥!
If you find this article useful so far, can I borrow you 1 minute to share this pin below? <3
I will also add some discount codes from the outfits, so pin them for later!!
THANK YOU FOR PINNING LOVE! I’m sure you’re a lady with good taste woohoo! Bless you ♥
5. High street derby day outfits ❤️👇🏼
While pastels and spring fashion are the theme of Derby Day, these days, more and more ladies embrace the high street style unapologetically. 📸
Below is some real-life high street look on Derby Day.🌸
Seriously, if you are feeling black and white, I’d say lean into it. ⚫⚪
Kentucky Derby fashion has been more diverse these days and that’s actually so cool!
6. MATCHING DERBY OUTFITS FOR COUPLES ❤️👇🏼
If your bae hates wearing couple matching outfits, the Derby party probably is the only time he is willing to break the rule!💑
It’s always worth it to match your derby look with your partner for some lovely photoshoots.📸💕
If you don’t want to look too matchy-matchy, echos the hue with the dress and the tie is always the fail-proof way to go. 🎨
Another way is wearing the same color but in a slightly different tone.
If he is wearing a baby blue suit, you can go for a deeper shade of blue for an elegant look.
That way, it just creates more dimension to the couple’s outfit as a whole!💞
This look is e.v.e.r.y.t.h.i.n.g. 😍✨
Youthful, fun, and preppy. 🎉
This is so random… BUT
hey ladies, why not quickly do an affirmation and feel instantly better?
This new year, I’m trying not only to share fashion tips but come up with ways to instill body positivity in all women who are reading my articles – aka YOU!
Instead of just reading it, say it loud or murmur the quotes (if you are in public) to maximize the effect.
Ready? Here we go.
I love my body. She is my forever home and sanctuary.
Sassy isn’t a shape, it’s an attitude.
Work out because I love my body – not because I hate it.
I can love myself and change my body at the same time. No guilt about that.
It is completely normal to have tummy rolls. I come to realize that social media isn’t showing the reality… at all.
My happiest moments in life had nothing to do with the way my body looked.
I don’t have to be pretty like her, I can be pretty like …ME.
I AM perfect imperfection.
What are your thoughts on that? I hope that makes you feel better (as you deserved).
Please help me pass the body positivity message in your community. #womenhelpwomen
Alright, now keep on reading!
7. GO MONOCHROME FOR A MODERN LOOK ❤️👇🏼
When in doubt, go monochrome.
Sometimes finding outfit ideas for an important event like the Kentucky Derby can easily down the rabbit hole. 🌀
Let’s be real, we’ve all been there. 🙃
You are all thrilled and pin all the looks you can possibly find on the Pinterest board and 2 hours later, you are feeling overwhelmed and exhausted. 😩
If you want to look put together with minimal effort, go for a monochrome look.🎨👌
Incorporating all kinds of similar shades together, just makes you look more united and again, elongates your figure.
To me, monotone wearing just always looks so high fashion even in the simplest ensemble.👗✨
8. AESTHETIC DERBY OUTFITS FOR PLUS-SIZE ❤️👇🏼
For all the plus-size ladies out there, of course, I won’t miss you!💖
After examining all kinds of looks, I’ve come up with the top 3 flattering styles. 🌟
A. Peplum dress ❤️👇🏼
Featuring a stripe of extra fabric at the waist area, it just seamlessly covers the belly area and you don’t have to wear the Spanx. 🙌
Plus, it just hugs your curves perfectly and showcases the hourglass shape. ⏳
Need I say more? This dress will look fabulous with a golden brown accent belt and a coordinating hat. 🌼💕
Such a darling piece. 💖
B. Off-shoulder dress 💓👇🏼
It’s almost universally flattering to showcase the neckline and shoulder line.
Plus, this neckline can balance off the heaviness of your long ruffle dress. 💁♀️✨
Or else, one-shoulder is a great way to shed the upper chest heaviness! 🎀
The best part? It just looks ultra stylish.🌟
C. Asymmetrical hem dress❤️👇🏼
Seems no one talks about it but the asymmetrical hem dress is surprisingly leg-flattering. ✨
This unique hemline not only makes you look ultra-chic but most importantly will draw attention to your legs vertically. 💫
Well, this lady obviously knows how to showcase her curves in the best possible way! 💖
This dress below isn’t asymmetrical, but it looks perfect fthe or Kentucky Derby! 🌼
My jumpsuit lookbook for plus-size babe 💕
Save this post and check out my LTK account later! ❤️
Continue to scroll down if you’re not interested! 📜
( ´ ▽ ` )ﾉ MY AUG PICKS !! ʕ•̬͡•ʔ
(Continue scrolling for the article!)
9. GET A HEEL PROTECTOR OR WEAR CHUNKY HEELS ❤️👇🏼
Wondering what shoes to wear for the Kentucky Derby? Definitely heels!
Specifically, all kinds of aesthetic heels can elevate your look to another level.
But here’s the thing. Is it possible to walk on the grass confidently with stiletto heels?
Yes, it is possible if you have this transparent little high-heel protector.
I bought it from Amazon and that’s a life-changer for me. 🫶🫶🫶
If you ever wonder why those girls can look so effortless on the grass, well, now you know the secret. 💅🏻
Of course, you can wear chunky heels if you are wearing more on the casual side. ✨
And guess what? Some ladies wear flats and still look so put-together. Impressed!
For me, I will still insist on wearing sexy heels and perhaps bringing a pair of ballet flats with me just in case.
As promised, here’s the video about rolling up jeans elegantly – not the typical way you think! Enjoy my loves <3
Want more feminine fashion inspo? Check out my newly set-up insta @hannahnfashion for more <3 See you there pretty ladies!
CLOSING THOUGHTS❤️:
So ladies, here are the 18 Kentucky Derby outfits for ladies.
That’s a long read but I truly hope these tips get you inspired to find your perfect derby party dress!
Let’s have a quick recap first:
- Stay elegant with classy derby outfits
- Keep it casual with a jumpsuit
- Kentucky Derby looks for cold weather
- Top it off with a perfect hat
- Matching derby outfits for couples
- Go monochrome for a modern look
- Aesthetic derby outfits for plus-size
- Get a heel protector or wear chunky heels
By the way, if you are interested in spring parties look.
I’ve just written one for tea party attire! Check it out here for 27 lovely looks!
For more horse racing event outfits, check out this blog post below <3
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