What I Wore Last Week – Kentucky Derby Edition

Kentucky Derby Blogger Outfit Ideas

Hope you all are having a great week! I wanted to share a little outfit round up of most of what I wore last week in Louisville, Kentucky and a couple of outfits here in Chicago, too. There wasn’t a full-length mirror in my room so I apologize for all of the selfies, haha.

Eliza J Midi Dress, Denim Jacket, White Sandals, Casual Spring Outfit

BaubleBar Earrings, Denim Jacket, Striped Midi Dress

May 1st  |  Dinner at Proof in Louisville

Eliza J Dress (will be online next week!)  |  Sam Edelman Sandals  |  Michael Kors Bag (currently on sale!)  |  Gap Denim Jacket (old; similar here)  |  BaubleBar Earrings (old; similar here)

Bows & Sequins wearing a Vineyard Vines Seersucker Wrap Dress at the Woodford Reserve Bourbon Distillery.

Preppy blogger Bows & Sequins at the Woodford Reserve Bourbon Tour in Kentucky wearing a Vineyard Vines seersucker dress.

May 2nd  |  Woodford Reserve Bourbon Distillery Tour

Vineyard Vines Seersucker Wrap Dress  |  Sam Edelman Sandals  |  BaubleBar Flower Earrings (old; similar here & here)  | Brahmin Handbag (similar here & here)  |  Prive Revaux Sunglasses  |  Kendra Scott Charm Bracelet

Chicago blogger Jessica Sturdy of Bows & Sequins wearing a pink Vineyard Vines dress at Oaks Day for the Kentucky Derby with pink tassel earrings, a pink fascinator, and white shoes and bag.

Chicago blogger with feminine style Bows & Sequins wearing all pink at Oaks Day at the Kentucky Derby in the Angry Orchard VIP Infield Club with the best view of Churchill Downs.

Blogger Bows & Sequins at the Kentucky Derby wearing a pink Vineyard Vines Dress, round Brahmin Bag, and white ankle strap sandals.

May 3rd  |  Kentucky Oaks Day at Churchill Downs

Vineyard Vines Bow-Back Dress  |  Vineyard Vines Fascinator  |  Vineyard Vines Tassel Earrings  | Brahmin Handbag (similar here & here)  |  C.Wonder Heels (old; similar here, here, & here)  |  Lipstick: NARS ‘Promiscuous’ + BareMinerals ‘Shameless’

Beauty blogger Jessica Sturdy wearing a Zara Sequin Turban Headband with red lipstick and a white dress.

May 3rd  |  Dinner at Butchertown Grocery

Eliza J Dress  |  Zara Sequin Turban (sold out; similar here)  |  Lipstick: NARS ‘Dragon Girl’ + BareMinerals ‘Juicy’  |  Clare V Leopard Clutch  |  Kenneth Cole Lex Heels

You can see this sequin turban on the blog here!

Preppy blogger Jessica Sturdy of Bows & Sequins at the Kentucky Derby wearing a blue fascinator, lace Vineyard Vines dress, Boden heels, and a J.Crew Striped Clutch.

Kentucky Derby Fascinator + Kendra Scott Earrings

May 4th  |  145th Kentucky Derby

Vineyard Vines Lace Dress  |  Vineyard Vines Fascinator  |  Kendra Scott Earrings  |  Boden Heels  |  J.Crew Striped Clutch (old; similar here & here)  |  Lipstick: BareMinerals ‘Juicy’

Chicago blogger wearing a denim jacket, tiered red maxi dress, Michael Kors editor bag, and flat espadrille sandals.

May 5th  |  Cinco de Mayo in Chicago

*pls ignore the mess, I had gotten home two hours prior!

Tuckernuck Dress (old; similar here, here, here, & here)  |  Express Denim Jacket (similar here)  |  Michael Kors Bag (currently on sale!)  |  Michael Kors Flat Espadrille Sandals (currently on sale!)  |  Loopy Case

You can see this dress on the blog here, here, & here!

Chicago blogger wearing a Nordstrom pointelle sweater with Vineyard Vines seersucker pants and white perforated loafers for spring.

May 6th  |  Coffee Meeting at 3 Arts

Halogen Pointelle Sweater (sold out; similar here, here, & here) |  Vineyard Vines Seersucker Pants  |  Sam Edelman Loafers (similar sandal style here)  |  Louis Vuitton Bag  |  Loopy Case

I wore a similar outfit in this post! You can see these shoes in this post and this post, and this sweater in this post.

Leave a Comment


  1. 5.8.19
    Briana commented:

    Living for the sweet head pieces!


  2. 5.9.19
    Maureen commented:

    As always, so many cute dresses and love those head pieces!

    Maureen | http://www.littlemisscasual.com

  3. 5.9.19
    Alyssa commented:

    I LOVED that headpiece with the white dress and red lip on your stories! So cute! (And not at all too extra)