Every day, we wake up hoping for a cool morning that calls for a coat or cozy sweater, and we’re confident October will finally grant us that! The new month brings plenty of autumn-themed events, including the return of Cheekwood’s famous pumpkin houses. We gathered our What to Wear team and spent the morning exploring the fall decor (on a laughably warm 99-degree day) at Cheekwood, and today, we’re sharing the breakdown of how to dress for three of Nashville’s biggest fall events: the Artclectic Patrons Party, Cheekwood Harvest and Once in a Blue Moon!

Leave it to Cynthia Kelley, our fantastic stylist, to effortlessly dress our models in on-trend, event-appropriate outfits that may or may not have left us with a desire to shop for a new season. She pulled clothing from Gus Mayer, Elle Gray and SB Shop, so you know it’s good. Since our models, Danielle Gilbert, Ingrid Perdikis and Caroline Shockley, are the co-chairs of USN’s art show, Artclectic, we finished their looks with Margaret Ellis Jewelry, a participating artisan in Artclectic this year. Stop by any of these shops to pick out these looks, or to pull together similar ones, for all of your October dressing needs!

The Event: Artclectic Patrons Party

  • Thursday, October 24, 2019
  • Cocktail attire
  • University School of Nashville
  • 6:30 p.m. to 9:30 p.m.
  • Tickets are $125 per person; Innovator donations are $250 per person and include a ticket to the Innovators Reception at 6 p.m.

Each year, we look forward to University School’s annual art show, Artclectic, which showcases an appropriately eclectic mix of established and up-and-coming artists. The show benefits the Fund for Innovative Teaching at University School of Nashville, promoting curricular innovation and classroom excellence. This year, more than 60 artisans will display their fantastic works in different mediums and at varying price points. All weekend long, art lovers can peruse a creative mix of paintings, photography, ceramics, jewelry, sculpture and more. The fun kicks off with Thursday night’s Patrons Party, where attendees can be among the first to see and shop the collections.

What to wear: For the Patrons Party, select your favorite cocktail attire — something just a touch fancy to celebrate the beginning of an art-filled weekend. The signature color for the event is cerise, and if you can manage to add it into your ensemble, you can help these chairs and their team add a splash of color — matching the decor and the featured cocktail! Add a fun accessory or a piece of statement jewelry, because, after all, it’s creativity we’re celebrating.

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These three lovely ladies have been hard at work chairing the upcoming Artclectic weekend (and modeling for What to Wear)!

On Ingrid: From Gus Mayer: Red jumpsuit, $390; snakeskin bag, $325 | From Margaret Ellis Jewelry: Black tourmaline negative space cuff, $490; black spinel can earring in bronze, $315

On Caroline: From Gus Mayer: Black patterned dress, $395; leather jacket, $605 | From Margaret Ellis Jewelry: 4-inch Gypsy hoop earrings, $200; circle pendant necklace in silver/bronze, $290

On Danielle: From Gus Mayer: Blue dress, $440 | From Margaret Ellis Jewelry: Oval noisette earrings, $325

The Event: Once in a Blue Moon

  • Saturday, October 26, 2019
  • Glen Leven Farm
  • 6:30 p.m. to 11 p.m.
  • Blue Moon tickets are $250 and New Moon Tickets (for ages 35 and younger) are $125.

Gather at Glen Leven Farm for their annual Once in a Blue Moon fundraiser. The evening raises funds for The Land Trust of Tennessee’s mission “to conserve the unique character of Tennessee’s natural and historic landscapes and sites for future generations.” The stunning backdrop of a 64-acre farm beneath the stars promises a fun and festive fall evening. Enjoy a seated, farm-fresh dinner, craft cocktails, a bonfire for roasting s’mores and live local music.

What to wear: It’s a jeans and boots kind of night! This evening is your chance to bring out the fall clothes you’ve been waiting to wear (or to shop for something new). It’s bound to be a cooler event since it’s outdoors, so layers are key. Incorporate autumn colors like jewel tones and camel, or try out a fall trend like snakeskin.

On Danielle, from Gus Mayer: Snakeskin accent jeans, $118; tweed jacket, $285; white blouse, $165; purse, $148

On Caroline: From Elle Gray: Navy dress, $68 | From Gus Mayer: Snakeskin purse, $455 | From Margaret Ellis: Ellipsoid chain necklace, $875; ellipsoid chain cuff, $740

On Ingrid: From Gus Mayer: Green snakeskin top, $598; camel jacket, $650; black jeans, $98; ‘Love’ purse, $298 | From Margaret Ellis: 4-inch Gypsy hoop earrings, $200

Cynthia reminded us that the snakeskin trend is going nowhere fast … try it on jeans, a top or a handbag!

The Event: Cheekwood Harvest

  • Through Sunday, October 27, 2019
  • Fall casual
  • Cheekwood Estate and Gardens
  • Tuesday through Sunday, 9 a.m. to 5 p.m. with additional hours on Thursdays from 5 p.m. to 9 p.m.
  • General admission tickets to Cheekwood are $13 for kids 13-17 and $20 for adults.

There’s no better place to celebrate fall’s arrival than festive Cheekwood Harvest. We had the chance to shoot this month’s What to Wear there, and even with nine different looks, we couldn’t take advantage of all of the many picturesque backdrops. The new season brings changing leaves, as oaks, maples, dogwoods and other trees turn orange and yellow and gold. There are kid-, adult- and family-friendly activities all season long, and you simply can’t miss the two highly anticipated pumpkin houses!

What to wear: Casual comfort is key as you wander through the gardens of Cheekwood. One of our favorite fall trends is a graphic tee paired with a blazer for a fun high-low look. Our SB Shop ‘ROAR’ tee is a bold yet playful closet staple, encouraging women to stand strong and courageously, living with abundantly loud love. Or, keep it super simple with a trendy one-piece jumpsuit and sneakers.

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On Danielle: From SB Shop: Roar tee | From Elle Gray: Camel blazer, $124 | From Margaret Ellis Jewelry: 8-inch Gypsy hoop earrings, $265

On Ingrid: From Elle Gray: Snakeskin jumpsuit, $139 | From Margaret Ellis Jewelry: Black spinel strip earrings, $250

On Caroline: From Elle Gray: Orange and blue blouse, $85 | From Margaret Ellis Jewelry: 4-inch Gypsy hoop earrings, $200; circle pendant necklace in silver/bronze, $290

Cheers to the end of a hot and fun day at Cheekwood!

A little behind the scenes …

What to Wear moves smoothly and stylishly, with many thanks to this gal! If you’re looking for a little additional fall wardrobe guidance, check out Cynthia’s new website for personal styling appointments and tips!

Leslie Moore from Private Edition keeps our models looking picture-perfect all day long … and always brings the laughter, too! If you are looking for makeup advice and tips, stop by Private Edition or The Cosmetic Market and see Leslie or any of their talented makeup artists.

Resources and special thanks:


For more on what’s going on in Nashville, visit our Happenings page for many more local events!