It’s no secret that we LOVE May here in Louisville. The weather is glorious, and the weekends are filled with live music, art fairs, flea market fun, graduations, weddings and more. Oh, and we have that one big event at Churchill Downs the first Saturday in May – the 143rd Kentucky Derby! There are so many May events that it’s tough to pick just three favorites, but we’re betting on Derby week events and some of our favorite looks for them: the Great Steamboat Race, Derby Eve galas, Oaks Day and Derby Day. And since May in Louisville is more than just Derby (as much as we love it), we also pulled looks for CycLOUvia in Three Points – Germantown, Schnitzelburg and Shelby Park – and WFPK Waterfront Wednesday on the Big Lawn at Waterfront Park.

These gorgeous May looks all come from locally owned boutiques we love – Peacock Boutique, Gifthorse and Colokial Boutique – and range from stylishly casual to gala-ready. Our lovely models this month, Shelby Shenkman and Leigh Anne Albrechta, are Louisville Ballet Company Dancers. Be sure to catch them in performances during the Ballet’s 2017-2018 season starting in September. We all had a great time shooting in this historic NuLu courtyard with one of the ballet’s favorite photographers, Sam English. Sam is also an amazing equine photographer who is well-known for shooting the Derby at Churchill Downs, making him our perfect pick for capturing May in Louisville.

Ready to race into May in style? Let’s go!

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Meet our beautiful May What to Wear models and Louisville Ballet Company dancers, Shelby Shenkman and Leigh Anne Albrechta.

The Event: Derby Week Fun

  • Great Steamboat Race, Wednesday, May 3, 2017; | Kentucky Oaks: Friday, May 5, 2017 | Derby Eve galas, Friday, May 5, 2017 | Kentucky Derby 143: Saturday, May 6, 2017
  • Oaks & Derby are at Churchill Downs, 700 Central Ave. | The Great Steamboat Race can be viewed from the riverfront or on board the Belle of Louisville or Belle of Cincinnati | Derby Eve galas happen throughout Louisville
  • Check out our May Event Highlights here for information about Derby Week fun locations, tickets and more.

The Kentucky Derby Festival officially kicked off with Thunder Over Louisville, but Derby week is when Louisville really starts the party. When it comes to getting work done during Derby week, the popular refrain from most everyone we know is, “Talk to me after Derby.” And why not? Every city deserves its traditions and festivities around it, and Louisville is no exception. Hooray! We picked a variety of looks and styles to fit the range of fun events this exciting week brings.

What to Wear: For the Great Steamboat Race, whether you attend a private party, ride the Belle of Louisville or join the crowds on the waterfront, keep it stylish and comfortable. We found Oaks and Derby looks filled with florals and prints – accompanied by the perfect hat, of course. And we suggest chic simplicity of black and white to strike a sophisticated tone for Derby Eve galas.

Look #1: Great Steamboat Race

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From Colokial Boutique on Shelby Shenkman: blue boat print button down, $59.99; belted high-waist denim capris, $79.99

Look #2: Kentucky Oaks Day

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From Peacock Boutique on Leigh Anne Albrechta: black with pink polka dots cold shoulder dress by McQ, $495; pink feather fascinator by Formé Millinery, $220

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Another stunning view of this McQ dress and Formé Millinery fascinator

Look #3: Kentucky Oaks Day (or Derby)

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From Gifthorse: floral pouf sleeve cocktail dress, $38

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More details from this Gifthorse Oaks or Derby look: rose trimmed hat, $145; gold tone horseshoe earrings, $10; gold tone bridle necklace, $45

Look #4: The Kentucky Derby

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From Colokial Boutique: rose appliqué sheer swing dress, $169.99; black fascinator by Ruby & Cordelia Fine Millinery, $130

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A closer look at the appliqué detail and chic black fascinator

Look #5: Derby Eve Gala

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From Gifthorse: sleeveless black faux leather and white chiffon dress, $42

Look #6: Derby Eve gala

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From Peacock Boutique: black silk slip dress by Rag & Bone, $599

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Metallic strap detail from this striking Rag & Bone slip dress

The Event: CycLOUvia in Three Points

  • Saturday, May 13, 2017
  • 2 p.m. to 6 p.m.
  • Germantown, Schnitzelburg and Shelby Park neighborhoods via Goss Avenue, Logan Street and Shelby Street

CycLOUvia makes its 2017 debut by returning to Three Points – the Germantown, Schnitzelburg and Shelby Park neighborhoods– on Saturday, May 13. This fun event opens streets to people only – no vehicles are allowed – and moves through neighborhoods via Goss Avenue, Logan Street and Shelby Street. This edition of CycLOUvia will take place during Better Blocks, a temporary installation at Oak and Logan Streets, with pop-up shops, vendors, public space, art, special performances and more. Jump on your bike, take a walk and play in the street.

What to Wear: Anything comfortable, especially shoes! We think you should also stay stylish since this is like a fun, participatory parade. Pick a light and fun cotton print dress (with bike shorts underneath) for a pretty, vintage vibe.

Look #1:

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From Gifthorse: sleeveless cotton multi-striped dress, $52

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We love pairing a pretty cotton dress with cute sneakers

Look #2:

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From Colokial Boutique: vintage style critter print cotton dress, $53.99

Full view of this sweet and stylish critter print dress

The Event: WFPK Waterfront Wednesday

  • Wednesday, May 31, 2017
  • Music starts at 6 p.m.
  • Big Four Lawn, Waterfront Park
  • This is a free event. No tickets required.

This free outdoor concert series is one of Louisville’s favorite summertime events and draws a big, enthusiastic crowd. May’s Waterfront Wednesday lineup features local and nationally known musician, Peter Searcy; Queens, New York-based roots-rock band, Hollis Brown; and wraps with headliners, The Mavericks. Grab your friends – or run into most of them there – and head out for a fun night out under the stars.

What to Wear: Stay comfortable and watch the weather, but stay bohemian chic. Jeans and an eye-catching top work well, or pull on a light, flowy dress to make dancing a breeze.

Look #1:

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From Peacock Boutique: black and white print off-the-shoulder top by Rag & Bone, $325; Lily Dale distressed denim capris by Rag & Bone; $285

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Stay comfortable and stylish at WFPK Waterfront Wednesday in these pieces from Peacock Boutique.

Look #2:

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From Colokial Boutique: tie-neck boho print dress, $73.99

Have a fantastic May, Louisville! We can’t wait to see you out there soaking up the fun.

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