Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas

Maggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

Derby Day is less than two weeks away, and as they say, it’s the most exciting two minutes in sports. Whether you’re at Churchill Downs or in your backyard, it’s every southern belle’s favorite excuse for getting dressed up and throwing a party. Contrary to popular belief, literally zero knowledge of horse racing is required to partake, which has always been a plus for me, and the day really just become a fun excuse to connect with neighbors and friends. That being said, there is a heavy emphasis placed on fashion. So, if you’ve got no idea what to wear to the Kentucky Derby or any local Derby Day festivities, I’ve partnered with Maggy London to create the ultimate Derby Day Style Guide! From cocktail dresses to fascinators, keep reading for 3 head-to-toe Kentucky Derby outfit ideas in today’s post! 

Look #1: Pink on Pink

Maggy London Alyssa Midi Dress styled with a pink fascinator headband, straw pom pom and tassel clutch, and nude Steve Madden wedges, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

Derby Day is all about color. Whether your ensemble is monochromatic or accented, don’t be afraid of color. That’s why I love the Alyssa Midi Dress. The gorgeous shade of pink makes me smile, and I don’t think I’ve ever seen a more Elle Wood-approved work dress than this one. Plus, it’s fully-lined with slight stretch that’ll keep you comfortable and confident all day long. For reference, I’m wearing a size 0. 

Funnily enough, this is the same fascinator headband I wore with my DIY flamingo costume last Halloween. You can easily spend top dollar on derby hats, but I found this little gem on Amazon for under $15. To match my costume, I removed the black veil and added in some pink feathers from one of my boas. The feathers actually make quite a statement, so if you want to add a little more pizzazz to your store-bought fascinator, try gluing in some cheap craft store feathers! 

Maggy London Alyssa Midi Dress styled with a pink fascinator headband, straw pom pom and tassel clutch, and nude Steve Madden wedges, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggy London Alyssa Midi Dress styled with a pink fascinator headband, straw pom pom and tassel clutch, and nude Steve Madden wedges, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggy London Alyssa Midi Dress styled with a pink fascinator headband, straw pom pom and tassel clutch, and nude Steve Madden wedges, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

Another way to add color to a derby outfit is with a fun clutch. I ordered this straw pom pom and tassel clutch off Amazon last year, and it’s one of my favorite Amazon purchases of all time. My only gripe is that is flies in and out of stock almost erratically. So, if you love it, grab it while you can.

Maggy London Alyssa Midi Dress styled with a pink fascinator headband, straw pom pom and tassel clutch, and nude Steve Madden wedges, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteShop the Look: Alyssa Midi Dress | Pink Fascinator Headband | Nude Wedges (old– similar style linked!) | Straw Pom Pom and Tassel Clutch | Pearl Stud Earrings

Look #2: Classic Seersucker

Maggy London Cecilia Midi Dress styled with a white fascinator headband, white Chloe Nile dupe bag, and espadrille slide sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

Seersucker was once dubbed the official fabric of the Southern Summer for good reason– it’s classic and lightweight. That’s why I was immediately drawn to the Cecilia Midi Dress. I absolutely love this dress. Not only is it perfect for Derby Day, it can be worn on repeat throughout the remainder of spring and summer. Plus, the soft floral embroidery takes its sweet feminine flare to another level. For reference, I’m wearing a size 0. 

Truth be told, I’m actually not a big fan of derby hats. They’re typically pretty heavy, and they start to hurt my head after an hour or so. So, I pretty much stick to fascinators, and they haven’t failed me yet. I paired the Cecilia Midi Dress with a larger white fascinator I snagged from eBay a couple years ago. This exact fascinator is no longer available unfortunately, but I found this nearly identical style on Amazon for under $20!

Maggy London Cecilia Midi Dress styled with a white fascinator headband, white Chloe Nile dupe bag, and espadrille slide sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante Maggy London Cecilia Midi Dress styled with a white fascinator headband, white Chloe Nile dupe bag, and espadrille slide sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggy London Cecilia Midi Dress styled with a white fascinator headband, white Chloe Nile dupe bag, and espadrille slide sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

Also, large purses are actually prohibited from the Kentucky Derby for safety reasons, so clutches are the traditional go-to. However, small convertible crossbodies, like this Chloe dupe bag, are my personal favorite. When your hands are full of snacks and mint juleps, just attach the strap and throw it over your shoulder. Easy peasy. 

Maggy London Cecilia Midi Dress styled with a white fascinator headband, white Chloe Nile dupe bag, and espadrille slide sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante Shop the Look: Cecilia Midi Dress | White Fascinator Headband | White Bracelet Crossbody Handbag | Espadrille Slide Sandals | Pearl Stud Earrings

Look #3: Pops of Red

Maggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante

I said before that Derby Day is all about color. While that’s true, bold pops of color can make an even bigger statement than all-over color combinations. That’s why I love this litttle red fascinator. I found it on Amazon for under $15 last year, and it’s served me very well ever since. It looks absolutely adorable paired with these red block heel sandals and just about any neutral black or white dresses you’ve already got hanging in your closet.

I was looking to go the more classic route in today’s post, so I picked the timeless Noreen Midi Dress. I absolutely love soft winter white in the spring, and this dress has a sweet ruffle detail that mixes its classic cut with a more feminine flare. Plus, it’s elegant enough to wear to formal engagements while still comfy and breathable enough to wear to the office and outdoor cocktail parties. For reference, I’m wearing a size 0.

Maggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a Debutante Maggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteMaggie London Noreen Midi Dress styled with red fascinator headband, GiGi New York Uber Clutch, and red block heel sandals, Derby Day Style Guide: 3 Head-to-Toe Kentucky Derby Outfit Ideas by affordable fashion blogger Stephanie Ziajka from Diary of a DebutanteShop the Look: White Ruffle Dress | Red Fascinator Headband | Red Block Heel Sandals | Stone Envelope Clutch | Pearl Stud Earrings

I’ve been celebrating Derby Day for years now, so there’s plenty more where this came from. If you need even more ideas for what to wear to the Kentucky Derby, click here! You can also grab the recipe for my favorite derby cocktail, which I consider to be a tastier variation of the Black-Eyed Susan, here. Enjoy your day at the races! 

I received these dresses from Maggy London as compensation for use in this Derby Day Style Guide. While these dresses were gifted, I only promote brands and products I genuinely love and believe in! Click here to read my full disclosure policy. Photography by Catherine Rhodes.

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