Derby Day

summer outfit little black dress dressed up with a blazer and heels and a hat

The Kentucky Derby is always one of my favorite days of spring. While I’ve admittedly never attended the actual Derby (one of these years I’m going to finally make the trip!), I’ve gone to my fair share of Derby parties over the years. What’s better than dressing up in your springtime finest (and preppiest!), donning an oh-so-chic hat, and drinking Mint Juleps with your guys and girlfriends?! Mark your calendars if you haven’t already… Not this weekend, but the next — May 7th!

summer outfit little black dress lace up sandals with wide brim straw sun hat

While I’m all for getting a dress specifically for the occasion (remember this post last year?), it’s nice to be able to shop your closet or pick up a dress that you’ll be able to wear over and over again, too! I recently got this dress (and blazer!) from Draper James, Reese Witherspoon’s clothing line. I’ve heard the boutique in Nashville is absolutely adorable, but until I get to Nashville… Online shopping it is! They’ve got so many cute finds on the site… great gifts (Mother’s Day is the day after the Derby!) and a ton of feminine frocks with a southern spin. And somehow by impeccable timing, today is the last day of their huge online sale — up to 75% off! Both my embellished dress and scalloped blazer are on major sale!

kentucky derby outfit black dress

black dress with white flowers, white jacket, summer straw hat wide brim

draper james white scalloped blazer

But back to Derby dressing… It’s nice to have dresses in your closet that work for a variety of occasions! I paired this LBD with a fun scalloped blazer and a wide brim hat for a look that’s Derby-Day-Approved, but you could easily ditch the hat and swap the sandals for a classic pair of pumps and you’ve got yourself an office-appropriate look. Or swap the blazer for a jean jacket and add a pair of ballet flats or white sneakers for the weekend. Options are endless when it comes to LBDs!

draper james dress with white embellished flowers

I absolutely love this little black dress! The pretty white embellishments at the neckline make getting dressed easy, no statement necklace needed. The texture is so pretty, too! Oh and did I mention it has pockets? It has pockets!!

goorin brothers straw hat

black dress with white blazer

What are your plans for the Derby this year? I’m still figuring out what to do for the day… Kind of toying with the idea of having a little get-together on the terrace at my apartment building because there’s an outdoor TV… TBD!

white scalloped blazer, black draper james dress with white flowers, valentino sunglasses

black dress with a white blazer and black lace-up heels

Get the Look…

Draper James Scalloped Blazer c/o
Draper James Embellished Dress c/o (also available in a skirt!)
Ivanka Trump Heels (available at Nordstrom, Zappos, Lord & Taylor, & Bloomingdales!)
Ivanka Trump Bag c/o (also available here & here!)
Valentino Sunglasses
Goorin Brothers Hat c/o Draper James
BaubleBar Pearl Studded Cuff (old, similar here & here)

goorin bros hat, white scalloped blazer, black draper james dress, black ivanka trump lace up heels

what to wear to a kentucky derby party black dress with a hat and heels

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Leave a Comment


  1. 4.27.16
    Polly said:

    Love the details of your blazer and those heels are so cute!


  2. 4.27.16
    Natali said:

    Looking flawless in this sophisticated and feminine outfit! Your dress is absolutely amazing!

  3. 4.27.16
    Lauren said:

    Can I just steal this entire outfit?! I’m obsessed with every piece! So cute!

    Fizz and Frosting

  4. 4.27.16
    Emily said:

    The scallops on that sweater are adorable! Great choice 🙂

  5. 4.27.16
    TAMMY said:

    I love the little black dress and the hat. Nice Blazer too. I can tell that you love those high heel sandals. I think those shoes are your go to sandal for the summer.

  6. 4.27.16
    Monika said:
  7. 4.27.16
    Lauren said:

    That dress is the absolute cutest and so perfect for the Derby! Also, I’m obsessed with those heels and have been lusting over them for forever!


  8. 4.27.16

    Love the scallop hem detail!

    Liz @

  9. 4.27.16
    Amanda said:

    You look adorable! Loving the hat and I’m always a fan of black and white looks.

  10. 4.27.16
    Sarah said:

    Look the look! How did you find Draper James sizing? I’ve been thinking about ordering but hate having to pay for return shipping.

  11. 4.27.16
    Lucy said:

    Oh my gosh, that scalloped blazer! It is just gorgeous, I love it! I especially love how you paired it with the dress & lace up heels. This outfit is 100% race ready!

  12. 4.28.16
    helena said:

    You look amazing. Love the hat 🙂

  13. 4.28.16
    Minau said:

    Such a great look’

  14. 5.28.16
    Emily said:

    these shoes are amazing! xo