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2023 29 Kentucky Derby lady real-life looks: regular + plus size!

2023 29 Kentucky Derby lady real-life looks: regular + plus size!

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.

what to wear kentucky derby festival
Source: Pinterest

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 baes stay tuned for the styling tips!

Enjoy ladies!


Source: 1,2,3

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.

CLASSY DERBY midi dress
Source: Nicole

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.

what to wear on Kentucky Derby
Get this hat on Amazon

Need I say more? So elegant!


Can you wear casual wear like jumpsuits for the Derby party?

Kentucky Derby jumpsuit outfit ladies
Source: ELLE

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 beam straw hat and espadrilles wedges just scream the delightful springy vibes.

HAT and black jumpsuit derby day
Follow @Taylor on LTK!

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.


As we all know, Kentucky Derby is an outdoor event and the weather can be pretty unpredictable sometimes.

KENTUCKY DERBY OUTFITS FOR winter, derby party outfits,
Source: 1,2

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!

white belted maje jacket
Shop this old money belted jacket from MAJE (45% off now!)

When the days are chilly out, a white puffy-sleeve sweater dress just looks so aesthetic.

COLD WEATHER kentucky derby white dress
Source: Pinterest


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.

derby hats, KENTUCKY DERBY OUTFITS FOR LADIES, derby party outfits,
Source: 1,2


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.

kentucky derby day hat
Source: Pinterest

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.

plus size hats derby
Source: Racingsavvy

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?

I will also add some discount codes from the outfits so pin them for later!!

what to wear kentucky derby women fashion

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.

high street derby outfit
Source: ELLE

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!

high street black and white kentucky derby outfits
Source: ELLE


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!

couple kentucky derby outfit

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!


When in doubt, go monochrome. Sometimes finding outfit ideas for an important event like Kentucky Derby can easily down the rabbit hole.

KENTUCKY DERBY OUTFITS FOR LADIES, derby party monochromatic outfits
Source: 1,2,3

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.

what to wear to kentucky derby party
Source: Pinterest

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.


For all the plus-size ladies out there, of course, I won’t miss you!

Source: 1,2,3

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.

amazon peplum dress plus size
Shop this gorgeous peplum dress on Amazon

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!

plus size one shoulder race day outfits
Source : Emily Walsh & milanoimai

The best part? It just look 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 know how to showcase her curves in the best possible way!

plus size race day outfit ideas
Source: Racingsavvy

This dress below isn’t assymmetrical, but on my, it looks perfect for Kentucky Derby!

kentucky derby plus size dress
Shop this statement dress on Amazon

Continue to scroll down if you’re not interested!

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(Continue scrolling for the article!)

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This YSL clutch screams the IT girl vibes. The best part? The price is *so forgiving*
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Obviously, this pheromone perfume (Amazon bestseller) is for the ladies who wanna spice things up (Got you gal!)
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Get a FENTY BEAUTY contour stick on Sephora ♡ (REAL inclusivity brand)
ysl mini shoulder bag
Get this YSL mini shoulder bag on Net-A-porter


KENTUCKY DERBY shoes for LADIES, derby party outfits
Source: 1,2,3

Wondering what shoes to wear for Kentucky Derby? Definitely heels! To be specific, all kinds of aesthetic heels can elevate your look to another level.

But here’s the thing. Is that 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.

wear flats to derby weekend
Source: Nicole

And guess what, some ladies actually wear flats and still look so put-together. Totally impressed!

For me, I will still insist wear sexy heels and perhaps bringing a pair of ballet flats with me just in case.


So ladies, so here are the 8 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!

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