With spring in full swing, it’s time to get down to business in the true fashion of a new month. Let’s figure out what to wear this May in Nashville! The long-awaited and truly appreciated warm weather has settled in, and it’s accompanied by the bright colors and patterns of spring styles. Iroquois Steeplechase, the 2019 Symphony Fashion Show, graduation season and Mother’s Day are coming up, so we’ve gathered an expert crew to show off these fabulous spring looks!

In celebration of the beautiful spring weather, we (boldly and thankfully, without rain) headed outdoors, to a beautiful backyard in Green Hills for this month’s photoshoot. From the pool house and the moss wall to the backyard overlook and exquisite greenery from every angle, we were certainly in awe of this breathtaking landscaping, which was designed by our talented friends at Page | Duke Landscape Architects. As another Nashville Symphony Fashion Show draws near, we looked to have the show’s co-chairs, Cynthia Arnholt and Allison Schaufele, join us in modeling these May fashions, fabulously styled once again by Cynthia Kelley. Take a peek at what this May has in store — for your calendar and your closet!

The Event: Iroquois Steeplechase

  • May 11, 2019
  • Race Day attire
  • Percy Warner Park
  • Gates open at 8 a.m.; first race starts at 1 p.m.
  • Individual tickets start at $75, with tailgating, group options and add-ons also available. Get yours here.

Join more than 25,000 spectators, both Nashvillians and visitors, at Percy Warner Park on May 11 for the treasured tradition of Iroquois Steeplechase. The 78th year of this beloved horse race is a must-attend event for May. Whether you’re just reserving your spot to tailgate, heading to the stands or kicking it from a skybox, this day reminds us year after year why we are indeed prioritizing Steeplechase festivities.

What to Wear: As if the festivities in and around the track weren’t exciting enough, creating our outfits always ups our anticipation of this beloved Nashville event. Embrace your “race day chic” in whatever way you’d like. Opt for bright colors, fun patterns and, of course, a great hat! We highly recommend that you also prioritize comfort. The day is long and can also bring rain, so be fun yet strategic with your wardrobe selection.

Look #1:

What to Wear this May in Nashville

On Allison, from Copper Penny: Floral dress, $142 | From Gus Mayer: Blue hat, $630

Look #2:

What to Wear this May in Nashville

On Cynthia, from Gus Mayer: Blue dress, $295; white hat, $980; white purse, $108

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Look #3:

What to Wear this May in Nashville

On Allison, from Copper Penny: Pink dress, $150; gold hoop earrings, $36; black hat, $60 | From Gus Mayer: Gold purse, $149

What to Wear this May in Nashville

This hat is perfect to wear all spring and summer long!

What to Wear this May in Nashville

And with that, they’re off to the races!

The Event: 2019 Symphony Fashion Show, presented by Gus Mayer

  • May 14, 2019
  • Cocktail attire
  • Cocktail hour begins at 6 p.m.; fashion show starts at 7:30 p.m.
  • Schermerhorn Symphony Center
  • General admission tickets are $250 each. Get yours here.

The Symphony Fashion Show is always a special springtime event in Nashville, and this year’s incredible lineup is no exception. Presented by Gus Mayer, the show is set to feature Carolina Herrera’s Fall 2019 collection, with a special appearance by Creative Director Wes Gordon and accompanied by a performance from featured entertainer Lauren Alaina. Be prepared to see fabulous fashion, enjoy an elegant night with community from around the city and raise money for the beloved Nashville Symphony!

What to Wear: Fashion lovers, this one’s for you! In anticipation for the beautiful looks from Carolina Herrera set to hit the runway at the fashion show, Cynthia styled Allison and Cynthia in the designer’s dresses. Use these gorgeous dresses as your inspiration for crafting a look for cocktail attire that has something different. Whether you play with varying lengths, festive sleeves, patterns that pop or unique cutouts, we love anything that makes you feel fabulous and ready to hit the runway yourself!

Look #1:

What to Wear this May in Nashville

On Cynthia, from Gus Mayer: Carolina Herrera white dress, $3,290

Look #2:

What to Wear this May in Nashville

On Allison, from Gus Mayer: Carolina Herrera polka dot dress, $2,490

Look #3:

What to Wear this May in Nashville

On Cynthia, from Gus Mayer: Black Carolina Herrera dress, $1,790; gold bag, $148

The Event: Mother’s Day & Graduations

  • Throughout May 2019
  • Elevated spring casual

From Mother’s Day brunch to the myriad other springtime celebrations, May is a busy month! This month brings a number of opportunities to sport some fun spring looks. Here are a few ideas.

What to Wear: The best way to prep for a busy season ahead is to solidify closet items that can transition from casual to dressy, from day to night, and from sitting to standing. We love a great solid dress that can be classy and clean or perfect for bold accessories. Play with different sleeve lengths, cuts and colors that make you feel your best and keep you comfortable for those long days, potentially spent in the sun.

What to Wear this May in Nashville

On Allison, from K. McCarthy: Seafoam green dress, $91; gold hoop earrings, $88

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What to Wear this May in Nashville

On Cynthia, from K. McCarthy: Blue dress, $238; drop earrings, $68

What to Wear this May in Nashville

On Allison, from Copper Penny: Pink dress, $116; hoop earrings, $86

What to Wear this May in Nashville

We couldn’t get enough of this gorgeous pink number, with a seemingly never-ending “sleeve”!

Enjoy your May festivities, whatever they may be!

A huge thank you to:

Take a peek behind the scenes…

What to Wear this May in Nashville

We also verified that this look is still cute with a necessary Steeplechase accessory — a raincoat! Shop this one from Copper Penny for $152.

What to Wear this May in Nashville

Our resident expert Cynthia Kelley knows exactly how to “top off” each outfit — and she can help you take the stress out of all your spring styling needs. Make your appointment now for her help to create custom ensembles for weddings, trips and beyond!

Kristen from The Cosmetic Market transformed the pool house to a studio and created perfect makeup looks for these May styles!

What to Wear this May in Nashville

An accurate sentiment for May in Nashville!

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For more on what’s going on in Nashville, visit our Happenings page. And for more on the local boutiques that provided these styles, visit our SB Guide.