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Get ready for a gorgeous June, Louisville! After the nonstop events that May always brings, we are ready for the start of a warm, laid-back summer. To celebrate the spirit of summer — its long, sunshine-filled days, afternoon picnics in the park, evenings catching fireflies (sigh) — we’re focusing on staying outside for this June edition of “What to Wear.” Our picks include a concert by Old Crow Medicine Show, performing under the stars at Louisville’s historic Iroquois Amphitheater; The Prelude, the Waterfront Botanical Gardens’ annual outdoor summer fundraiser; and the Kentucky Shakespeare Festival in Central Park, the oldest free Shakespeare festival in the country.

To keep you cool and stylish, we’ve pulled together breezy looks from three of our favorite local Louisville boutiques: Work the Metal, Liv Boutique and Betty Jeffries, our favorite boutique on wheels. We also included some stylish and comfortable footwear from Water + Oak Outdoor Co. And our lovely models — Alisha Espinosa, Chloé Bell and Jennifer Pennington — are cast members performing in this season’s Kentucky Shakespeare Festival, all summer long. We had a great time shooting in Kentucky Shakespeare’s summer home, Central Park in Old Louisville, and its beautiful next-door neighborhood, historic St. James Court.

Ready for summer fun in Louisville? Let’s go!

The Event: Old Crow Medicine Show

  • Friday, June 2, 2017
  • Doors open at 6:30 p.m.
  • Iroquois Amphitheater, 1080 Amphitheater Road in Iroquois Park
  • Tickets range from $39.50 to $49.50 each

The Grammy Award-winning, rootsy Old Crow Medicine Show travels through Louisville for a night under the stars at the Iroquois Amphitheater. On this tour the band performs Bob Dylan’s entire iconic album, Blonde on Blonde, for what we think will be an unforgettable night of country-infused folk rock by masters of the genre.

What to Wear: Odds are good that you’ll stay on your feet for this outdoor performance, so comfort is key. That said, a live concert is a great time to show some shoulder, to wear funky, statement jewelry and have fun with your look.

Look #1:

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From Work the Metal on Kentucky Shakespeare actor Alisha Espinosa: black and white gingham cold-shoulders top, $26; black pom-pom shorts, $22; strappy sandals, $26; florescent pink tassel earrings, $9

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Have fun with accessories — we love the pop of bright pink against the black and white! From Work the Metal: pink tassel earrings, $9; chunky black wooden bracelet, $44

Look #2:

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From Liv Boutique on Kentucky Shakespeare actor Chloé Bell: Bell Dahl olive off-shoulder dress, $142; gray shoulder bag with flower detail strap, $180; From Water + Oak: OTBT Bushnell wedge, $125

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Add drama with this white fringe necklace from Liv Boutique, $52.

Look #3

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From Betty Jeffries on Kentucky Shakespeare actor Jennifer Pennington: linen pastel stripe shirt dress, $69.50; From Water + Oak: Bussola “Mansfield” woven cork wedge sandals, $125; By Bear Branch Handcrafted: wood drop earrings, $20; wood and leather wrap necklace, $40

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Keep smiling in this summer-perfect shirt dress.

The Event: The Prelude

  • Sunday, June 4, 2017
  • Future Waterfront Botanical Gardens site, corner of River Road and Frankfort Avenue
  • Tickets: $175 each

Louisville’s Waterfront Botanical Gardens – an outdoor environment in development – again hosts its annual fundraiser, The Prelude, to support building the planned Education Pavilion and the surrounding gardens. Drinks and hors d’oeuvres will be provided by Atria Hospitality, and Louisville Ballet artists will perform with local jazz legend, Dick Sisto. This outdoor event happens on the site designated for the future Waterfront Botanical Gardens, promising a delightful afternoon of art and sunshine.

What to Wear: Comfortable, pretty florals, from flirty to sophisticated, seem like the perfect fit for an afternoon event celebrating a beautiful outdoor space in the works.

Look #1:

From Work the Metal: white pleated swing dress with white appliqué flower sleeve detail, $56; white drop statement earrings, $26; nude t-strap sandals; $26
From Work the Metal: white pleated swing dress with white appliqué flower sleeve detail, $56; white drop statement earrings, $26; nude t-strap sandals; $26
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Nothing like a flowy, flirty dress to make you feel like dancing.

Look #2:

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From Liv Boutique: Molly Bracken floral maxi dress, $88; pink quartz and fringe statement necklace, $128

This beautifully detailed beaded pink quartz and fringe necklace sets the stage.
This beautifully detailed beaded pink quartz and fringe necklace sets the stage.

Look #3:

From Betty Jeffries: green retro dress with flower power print, $54.50; From Water + Oak: OTBT Nomadic wedge, $139
From Betty Jeffries: green retro dress with flower power print, $54.50; From Water + Oak: OTBT Nomadic wedge, $139; By Bear Branch Handcrafted, wood drop earrings, $20

The Event: Kentucky Shakespeare Festival

  • May 31 through August 13
  • Pre-show begins at 7 p.m. with performances starting at 8 p.m.
  • C. Douglas Ramey Amphitheater, Central Park, 1340 S. Fourth St.
  • Free admission

For 11 weeks in the summer, Louisville’s beloved Kentucky Shakespeare Festival happens under the stars in Old Louisville’s beautiful Central Park. These are true community events and fun nights out, with food trucks, drinks available at Will’s Tavern and performances that even the youngest audience member can enjoy. This year’s performances include Much Ado About Nothing, Richard II and Julius Caesar as well as performances by community partners CenterStage, Louisville Ballet and Cincinnati Shakespeare Company and more. Performances are free.

What to Wear: Casual and comfortable rule the day at this outdoor event, so we suggest light and flowy tees, denim and seersucker for nights when the heat turns up.

Look #1:

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From Work the Metal: blue and white seersucker romper, $42; denim espadrille wedge, $28; pom-pom and tassel earrings, $14

Soak up the sunshine with bare shoulders this June.
Soak up the sunshine with bare shoulders this June.

Look #2:

From Liv Boutique: sheer detail tee by Young Fabulous & Broke, $98; white tassel earrings, $84; poppy jade bracelet, $28; Stiletto crop jeans, $196; cross body bag with embroidered guitar strap, $64; From Water + Oak: Birkenstock Mayari sandal, $125
Make a strong statement with tassel earrings.
Make a strong statement with tassel earrings.

Look #3:

From Betty Jeffries: Frock Shop navy with butterfly print dress, $79.50
From Betty Jeffries: Frock Shop navy and butterfly-print dress, $79.50; By Bear Branch Handcrafted, wood drop earrings, $20

Thanks to our Kentucky Shakespeare actors who took time from their busy rehearsal schedule for this fun outdoor shoot in their home away from home. And thanks to the Conrad-Caldwell House Museum for letting us use this historic home in St. James as our base for the day. 

And thanks to Sam English for capturing these gorgeous women in their element. 

Photographer Sam English in action in Central Park.
Photographer Sam English in action in Central Park.

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Natalie Harris