Plus Size Kentucky Derby and Oaks Style

The Kentucky Derby is one of the gem claim-to-fames of this fine Commonwealth I live in. It brings celebrities from near and far, some of the finest athletes in the country (the horses and the jockeys), and is a place to see-and-be-scene. There's also the mint juleps and other copious amounts of distilled beverage consumption. What's not to like?!

View all the latest Kentucky Derby Style posts here.

Trying to figure out what to wear to the Kentucky Derby or the Kentucky Oaks is always a little daunting. Everyone dresses to the nines, and if you enjoy being a little “extra” like I do, the opportunity to dress up and wear a hat or fascinator is not one to be missed. As a plus size woman, finding a Derby or Oaks dress can take a little more planning since bright and colorful dresses aren't always readily available at the boutique down the street. Thankfully, there are a lot of good options online, plus speedy shipping at many places.

Plus Size Kentucky Derby and Oaks Style 1 — My Kentucky Oaks outfit from a couple of years ago.

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Note, 4/21/19: This post is from 2018, so some items may no longer be available. I have updated with some more links, but also have a new section of Derby style ideas here.

Plus Size Kentucky Derby and Oaks Style 2 — See my 2019 Derby style ideas here

The Breakdown of a Plus Size Kentucky Derby or Oaks Outfit:

A springy dress. This year I predict we'll see some amazing jumpsuits as well at the track, but personally, the thought of undressing halfway, or all the way, in a bathroom stall at Churchill Downs isn't my idea of fun. So if you go the jumpsuit route, make sure you can get in and out of it easily and quickly. (But if you ARE considering a jumpsuit please let it be this one from ELOQUII – floral, one shoulder, and fringe – dying!) Because after 3 Kentucky Oaks Lillies, you WILL have to visit the ladies room a few times. I'll link some of my favorite dresses for this year at the end of this post.
A headpiece. Fascinator or hat – there are so many amazing options available. Go as big as you desire – there are very few events in the world that will let you get away with knocking people over with your hat. My biggest tip is to test it on your head for a bit before the day of the event. Some can be quite heavy and awkward, so reduce the self-consciousness a little by knowing what it feels like when you're wearing it. This also can help you determine if it will stay put all day, or if you'll need some extra reinforcement. It's important to remember that a headpiece doesn't need to match your outfit exactly, it just has to *go* with it. Play with color, texture, and scale! I had an amazing time recently trying on hats from The Hat Girls here in Louisville. They have amazing pieces in-store, and on their Etsy shop. I saw one of their pieces on a magazine cover years ago (pictured, left), and to my delight, they let me try it on in the store:
Comfortable Shoes. Even if you have great seats at the Derby or Oaks, you're going to be on your feet A LOT. Whether it's from your parking far from the track, milling around with drinks and people watching, or standing to cheer for the horses – it's crazy hard to be in uncomfortable shoes. I can't tell you the number of people I saw leaving, carrying their high heels in one hand, walking barefoot amongst the crowds. I realize shoes can really enhance an outfit, but going for a slightly less high fashion pair of shoes is more attractive than limping around, or barefoot. A wedge or block heel can give you a bit of elevation and style, without the pain of a stiletto. There are some very cute, wide width options at Zappos, Nordstrom, and Macy's (where I may have just purchased 2 pairs of these surprisingly comfortable pairs of heels)
A handbag. Don't go crazy and take your massive tote – there is a 12″ limit to bags. You also don't want to weigh yourself down with a large bag, given you'll have to hang onto it for 9+ hours. A crossbody is ideal, but if you're not forgetful, a clutch can work. Make sure to pack your ID, cash, lipstick, car keys, and pen so you can make your notes in the program. Plus you'll need a bag to stash those winning tote tickets!
Sunglasses. The weather is particularly fickle this time of year, so be prepared for rain or blinding sun. A pair of shades not only helps in the moments of brightness, it also let's you people watch without direct gawking.
Sunscreen. You'll be outside a very long time. Keep your skin protected.

Plus size Kentucky Derby or Oaks outfit ideas:

All Out Spring: For those of you who love color and florals like I do, this look is for you! You can't get much more literal for the Run for the Roses as wearing a rose printed dress. This one has a twist, as it's a bold print on black. I'd pair it with some nude or blush wide width low heels like these from Macy's. I love this headpiece from The Hat Girls because it is large scale but not a heavy weight. The color is neutral enough that it could go with many different dresses (and yes, you can wear your headpiece again. You spent the money – why not?!) The Kendra Scott earrings are large, but not heavy, and won't compete with the hat. The floral clutch may be overkill for some, but I think it's fun and playful.

Bold Oaks: The Kentucky Oaks is all about the pink! If you want to go bold and unabashedly Oaks obsessed, try this one. The Lane Bryant dress is a gorgeous, saturated fuchsia with enough flair to make it special. The bag is bright, bold, and looks like a taco – what's not to love? The fascinator is bold and airy at the same time. And the earrings I'm literally wearing as I type this – they're so fun. I kept it pink with the floral flats as well, because I love a theme. But, you could also tone it down with blush or nude shoes.

Derby Sleek with a Pop: I get it – not everyone loves wearing the rainbow. For those who love a modern and clean look, or are tied to black, this ELOQUII shirtdress is sharp and clean, and a black fascinator with a lot of structure. Give some dimension with bold earrings (I bought these this past weekend and am obsessed.) Optional color provided by a red clutch, and a swipe of bright lipstick. A metallic mid heel pump (these in wide width) is a safe bet.