September. To Nashvillians, the change between August and September really doesn’t mean too much as school is already in session and fall weather won’t arrive until October. One – perhaps the only – positive aspect of the extended summer heat is that it lends a new lease to your wardrobe. Transition attire is tricky, but you never have more options than when you can pair fall tops with your favorite shorts or that breezy sleeveless blouse with a new pair of jeans. We especially love the extra weeks it allows us to throw on summer sundresses: no outfit assembly required. Add accessories, and you’re out the door and on your way. (Not to mention the loose fitting shape of a dress will keep you far cooler than most pant-top combos!)

Today, we’re highlighting nine great dresses appropriate for fall events and beyond. Rebecca Thompson graciously selected and styled today’s gorgeous looks, also sharing a few fashion tips on contemporary and classic apparel alike. Our models are Cynthia Arnholt and Mary Wilson, co-chairs of the Mad Hatter Gala. You’ll want to mark your calendar for that event as well as the First Saturday Art Crawl and Music City Food + Wine Festival so you can show off transitional style in a new and exciting way!

We shot on location at 5th Avenue of the Arts inside The Arts Company, The Rymer Gallery, and Tinney Contemporary. Cynthia Arnolt and Mary Wilson, co-chairs of this year’s Mad Hatter Gala, graciously modeled Rebecca’s beautiful selections from Native + Nomad, Zelda and Gus Mayer.

The Event: First Saturday Art Crawl

  • Saturday, September 3, 2016
  • Free admission
  • Open to the public
  • For more information, click here.

Now in their 10th year of hosting the First Saturday Art Crawl, 5th Avenue of the Arts has a booming strip of galleries participating in the event, each with their own unique collection of art. September will be a wonderful opportunity to explore each space while sipping wine and chatting with local artists. Be sure to check out Tinney Contemporary, The Rymer Gallery and The Arts Company for great new exhibits – you can see peeks of their exhibitions in the photos throughout today’s article!

What to wear: We consistently see all types of attire at this monthly event and are big proponents of wearing what’s comfortable. But why not dress up your downtown excursion and make an evening out of it? Whether you head to dinner, lower Broadway or both, add some edge to your favorite dress with a unique wrap or statement jewelry. We like these looks from Zelda and Native + Nomad.

Look #1:

White looks great all year long - embrace the opportunity to be bright even in the fall and winter months!

Cynthia looks great standing outside The Arts Company in her Zelda ensemble. Rebecca shared with us the key of layer in transition seasons – wraps and cardigans are closet essentials in both fall and spring. They will keep you warm and add variety to an otherwise simple ensemble. From Zelda: tie-dye dress, $237; textured wrap-sweater, $372; labradorite necklace, $195

Look #2:

 Kick it up a notch in a modern jumpsuit!

Mary, Mary, quite contemporary in her white jumpsuit from Native + Nomad perusing the galleries on Fifth Avenue. Rebecca emphasized (and we quite agree) that white after Labor Day is perfectly acceptable – and a good thing! She also noted that the cropped jumpsuit is incredibly flattering and can lengthen one’s figure, but heels are a MUST. From Native + Nomad: Blaque Label jumpsuit, $171. From Gus Mayer: beaded fringe necklace, $215

Look #3:

Statement prints make accessorizing a breeze - less is more!

Bold, statement prints fit right in at Art Crawl — you never know what kind of modern pieces you’ll see on the walls of Rymer Gallery! From Native + Nomad: Blaque Label dress, $210

The Event: Mad Hatter Gala

  • Friday, September 9, 2016
  • Premier fundraising event for the Sexual Assault Center
  • For tickets and more information, click here.

The Mad Hatter Gala is the primary fundraising event of the Sexual Assault Center,  and this year, it moves to the Omni Hotel for what is sure to be an elegant evening. Co-chairs (and our What to Wear models) Cynthia Arnholt and Mary Wilson have put together this year’s benefit to celebrate and support survivors of sexual violence. With an annual attendance close to 400, you will certainly want to dress to impress!

What to wear: Attire is cocktail, so we recommend a statement number or a simpler solid that can be jazzed up with the right accessories. Gus Mayer was our go-to for gowns, baubles and bags alike!

Look #1:

 Ruching is a gal's best friend - even when she's in phenomenal shape like Mary!

Mary is sitting pretty at Tinney Contemporary. Her gold leaf dress is an absolute knock-out number. Our favorite feature? The ruching that enables you to sneak an extra bite or two without compromising the dress fit! From Gus Mayer: Carolina Herrera dress, $2,490; Kenny Ma clutch, $395; earrings, $125

Look #2:

Cynthia looks pretty in her pink frock from Gus Mayer!

Rebecca noted that while neutrals can be easier for day-to-day life, cocktail occasions are a great opportunity to wear something bright and exciting. Cynthia made quite an entrance at the top of the Tinney steps in this pink mid-length number! From Gus Mayer: Sachin & Babi Noir dress, $595; Kenny Ma clutch, $395; drop necklace, $155

Looks #3 & 4:

Cynthia and Mary are a welcoming and glamorous sight at the doors of Tinney! Rebecca shared that an LBD does not have to be plain, as you can see in the tiled detailing on Cynthia's dress. She also noted that navy is a great alternative, and she is a big believer in the LND (little navy dress). From Gus Mayer: Carmen Marc Valvo black dress, $640; earrings, $98; Kevin Hall navy dress, $1,650; pearl earrings, $125

Cynthia and Mary are a welcoming and glamorous sight at the doors of Tinney! Rebecca shared that an LBD does not have to be plain, as you can see in the tiled detailing on Cynthia’s dress. She also noted that navy is a great alternative, and she is a big believer in the LND (little navy dress). From Gus Mayer: Carmen Marc Valvo black dress, $640; earrings, $98; Kevin Hall navy dress, $1,650; pearl earrings, $125

The Event: Music City Food + Wine Festival

  • September 17-18, 2016
  • A weekend of samples from Nashville’s restaurants as well as beer, wine and spirits tastings
  • For tickets and more information, click here.

Prepare your tastebuds for a weekend they won’t soon forget. With cooking demos and panel discussions alongside samples of some of the city’s best bites and drinks, we can guarantee you’ll leave with a whole new approach to cooking in your own kitchen. Spice up your weekend with what’s sure to be a delectable experience!

What to wear: This is another event where you’ll see attire of all types, and we do encourage clothes that are easy to move (and eat!) in. Cool dresses with great accessories are a favorite option, especially in Nashville’s unpredictable fall weather! Looks from Native + Nomad or Zelda would add the right amount of bohemian chic to your ensemble!

Looks #1 & 2:

Cool and contemporary no matter the occasion, we love these looks from Native + Nomad and Zelda!

A friend and supporter of The Arts Company since its inception, GHP Environmental + Architecture’s offices sit above the gallery space. Recently dubbed “The Millennial Suite,” they offer a modern retreat and lovely view of downtown Nashville. Mary (left) and Cynthia’s fit right in with the industrial chic design in their chic apparel! On Mary, from Native + Nomad: Blaque Label white dress, $142. From Gus Mayer: beaded cross necklace, $165. On Cynthia, from Zelda: Comey black dress, $73; black & white wrap dress, $450; gold beads, $165

Look #3:

A breezy black dress is a closet staple, to be sure.

We love everything about the Rymer Gallery — even the front windows! Mary’s laid back style fits right in with the clean lines of the gallery space. Our favorite feature of her ensemble is its versatility — the strapless midi-length dress doubles as a maxi skirt! From Zelda: URU black skirt-dress, $168; Love Heals beads, $165 each

Get out and enjoy one of the best seasons in Nashville!

The beautiful photos from today’s What to Wear article were taken by Leila Grossman of Grannis Photography.

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