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Go, baby, go! It’s May, and that means event after event after horse-racing event. If you clicked on this article hoping to find what you should wear during Derby week, you won’t find it here. Instead, you’ll find it in our Derby Edition of What to Wear with styling tips from The Hat Girls! But, if you want to take a small breath from all of the Derby madness, keep reading, because we have a special treat for you.

Have you ever been stuck on how to accessorize your favorite little black dress or a simple jeans and t-shirt look? We asked our fabulous stylist Shannon Kessler from Primp Style Lounge to show us the ropes when it comes to polishing the perfect look. The clothes and accessories for this edition of What to Wear have come from Six Sisters, Cordial Lee, Clater Jewelers and 6pm Outlet. And we’ve paired these looks with equally-as-awesome upcoming local events: WineFest, the Buy Local Fair and Waterfront Wednesday. Our models are Heather Buford, Alexandria Sebian and Maddie Myers, former Miss Kentucky USA 2017. Let’s get started!

The Event: WineFest

  • May 1-2, 2018
  • 5 p.m. to 9 p.m., both nights
  • Tickets are $45, and designated driver tickets are $10.
  • For more info, visit kdf.org.

Calling all wine lovers! The Belvedere at Waterfront Park turns into a regional wine tour both nights of the Kentucky Derby Festival’s WineFest. More than 90 wineries in the area will have varieties available to sample. Entry includes a wine glass, an event pin and a chance to learn about the many red and white varietals from the Bluegrass State and surrounding areas.

What to Wear: Where there’s wine, a little black dress is divine! You can quote us on that. We love breaking out our little black dresses, and what a fun way to play around with accessories! Since spring is in the air, Shannon helped us infuse pops of color into three different black dresses for a total of five fun looks from Six Sisters, Cordial Lee, Clater Jewelers and 6pm Outlet. Take a look!

Look #1:

what to wear may louisville

On Maddie, from Cordial Lee: Nancy pleated dress in black, $49.95; pink fringe statement earrings, $17.50; long, pink beaded necklace, $25 | From 6pm Outlet: Pink pumps, $150

From Cordial Lee: White beaded bracelets, $9.95 each; gold handbag, $21.95

what to wear may louisville

Pink suede pumps, $150, from 6pm Outlet

Look #2:

what to wear louisville may

On Alexandria, from Six Sisters: Black keyhole-back t-shirt dress, $68 | From Cordial Lee: Gold handbag, $21.95 | From Clater Jewelers: Red rose pin, $44

what to wear louisville may

From Clater Jewelers: Real red rose twirl earrings, $44; real red rose blossom pendant, $39

what to wear louisville may

From 6pm Outlet: Red suede pumps, $125

Look #3:

what to wear louisville may

On Maddie, from Cordial Lee: Turquoise earrings, $9.95; glass and gold rhinestone bracelets, $8.95 each; turquoise bead necklace, $25

may what to wear louisville

Maddie is wearing the same dress from Cordial Lee as her previous look – we just switched up her accessories for a totally different vibe!

what to wear louisville may

From 6pm Outlet: Blue suede heels, $198

Look #4:

what to wear louisville may

On Alexandria, from Six Sisters: Black ruffle sleeve dress, $88 | From 6pm Outlet: Fringe boots, $113

what to wear louisville may

From Six Sisters: Beaded bracelets, $10 each; quatrefoil tassel earrings, $18; white stone necklace, $28

RELATED: How to Shop Smart, Curate a Dynamic Closet & More: Ask Megan

Look #5:

What to wear louisville may

On Alexandria, from Clater Jewelers: Sterling silver bar necklace, $57; knotted ball tassel necklace, $48

what to wear louisville may

From Clater Jewelers: Sterling silver hoops, $49

The Event: 10th Annual Buy Local Fair

Louisville loves to support local. It helps us to “keep Louisville weird” as the Louisville Independent Business Alliance likes to say. This will be the 10th Annual Buy Local Fair at the Louisville Water Tower Park, and the event will feature booths from a variety of local businesses, artists, craftspeople, community organizations and farmers, as well as live music, a cooking competition, food and retail vendors, a craft beer tent and a children’s area. It makes for an amazing day!

What to Wear: We’re keeping it casual for the Buy Local Fair. A simple t-shirt and jeans or a pair of shorts is perfect. Play it up with some fun statement accessories like we did in these looks from Six Sisters, 6pm Outlet and Cordial Lee.

Look #1:

May What to Wear louisville

On Heather, from Six Sisters: Black keyhole t-shirt, $34; yellow tassel earrings, $28

May what to wear louisville

From Six Sisters: Erimish light blue bracelet, $10 | From Cordial Lee: White beaded bracelet, $9.95

may what to wear louisville

From Six Sisters: White lace jeans, $104 | From 6pm Outlet: Floral mules, $200

Look #2:

what to wear louisville may

On Maddie, from Six Sisters: White t-shirt, $28; optic white lace detail jeans, $104 | From 6pm Outlet: Latte strap suede heels, $99

May what to wear louisville

From Six Sisters: Silver and white stone oval drop earrings, $18; stone and wood statement necklace, $44

The Event: Waterfront Wednesday

  • May 30, 2018
  • Lawn opens at 5 p.m.
  • Free to attend
  • For more information, visit wfpk.org.

It’s time again for the Waterfront Wednesday Concert Series at Waterfront Park — one of our favorite events of the summer! May’s free concert on the Big Four Lawn will feature music from J Roddy Walston and the Business, Sunflower Bean and Parker Millsap. Grab your chairs and blankets, pack a snack, and head down to the riverfront to enjoy an evening of music and fun.

What to Wear: We love summer dresses, but if you’re a little leery to wear a dress while sitting in the grass with snacks and a drink, we totally understand — that’s why we also threw in a pair of shorts, so you can move about without fear. Here are three looks — punched up with fabulous accessories, of course — that will make you feel comfortable, cute and fashion-forward from Clater Jewelers, 6pm Outlet, Six Sisters and Cordial Lee.

Look #1:

what to wear louisville may

On Heather, from Six Sisters: White lace dress with scalloped neckline, $58 | From 6pm Outlet: Pink pumps, $99

what to wear louisville may

From Clater Jewelers: Freshwater cultured pearl 18-inch strand, $250; raspberry pendant with Biwa pearls and white freshwater pearls, $165; white Baroque freshwater pearl and beaded bracelet, $44

RELATED: Shelby Packer of Cordial Lee: FACES of Louisville

Look #2:

what to wear louisville may

On Maddie, from Six Sisters: White t-shirt, $28; lace kimono, $68; blush pink and navy pattern shorts, $58; bone and navy tassel necklace, $34 | From 6pm Outlet: Blush flats, $65

what to wear louisville may

From Six Sisters: Deep gray stone earrings, $28

Look #3:

may what to wear louisville

On Alexandria, from Six Sisters: White lace dress with scalloped neckline, $58; multicolored drop ball earrings, $28; long purple tassel necklace, $34

what to wear louisville may

From 6pm Outlet: Mushroom suede wedges, $74

THANK YOU! THANK YOU! THANK YOU!

A look behind the scenes …

may what to wear louisville

Shout out to Shannon Kessler of Primp Style Lounge for always making sure our models look absolutely perfect!

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For more on what’s going on in Louisville, visit our Happenings page, and for more on the local boutiques that provided these styles, visit our SB Guide or download our FREE SB App.

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