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There is no shortage of fun, outdoorsy events in May. But before you can hang out with the coolest Atlantans in the city, you need to make sure you dress the part. We start the month off by appealing to your artsier side, with the Chastain Park Arts Festival; then it’s time to shake your knees — and bodies — to the amazing musical acts performing at Shaky Knees Festival. Lastly, show off those jazz hands … or just enjoy the sweet, melodious sounds of the Atlanta Jazz Festival. No matter what you enjoy or where you want to go, make sure you look stylin’ and get the event photographers clamoring to take your shot by making full use of our What to Wear advice.

The Event: Chastain Park Arts Spring Festival

  • Saturday, May 7, 2016, 10 a.m. to 6 p.m., and Sunday, May 8, 2016, 11 a.m. to 5 p.m.
  • Free to attend
  • Fine art, a children’s area, gourmet food trucks
  • Get more info online.

Celebrate the arts and handcraftsmanship at the sixth annual Chastain Park Arts Spring Festival in gorgeous Chastain Park. This free event welcomes some 185 painters, sculptors, jewelers, photographers and more, in addition to live demonstrations, entertainment and activities for the kids. Plus, gourmet food and beverage trucks will serve some of the very best bites to grab in the city.

What to wear: Chastain is a great place for people of all ages and interests who wear all sorts of different styles, which means the festival uniform is, well, un-uniformed. With all these different tastes, we had to go with an Atlanta boutique that knows how to dress a variety of women. Boogaloos is the perfect store to create three potential looks just right for a day at the festival and later dinner out with friends. We visited the Brookhaven location, but don’t forget there’s a Boogaloos in Decatur as well.

Look #1:


From Boogaloos: Floral tank, $116; white cigarette roll-up jeans, $178; electric blue tote, $145; white and pink necklaces, $138 and $158, respectively; white and pink bracelets, $44 each

Look #2:


From Boogaloos: Mustard tank, $79; teal tie shorts, $88; crossbody bag, $152; necklace, $98; bangles, $22

Look #3:


From Boogaloos: Army green shirtdress, $126; arrowhead pendant necklace, $158; brown clutch, $86; beaded bracelet, $114; earrings, $58

The Event: Shaky Knees Music Fest

  • Friday, May 13, 2016, through Sunday, May 15, 2016
  • Gates open at 11:30 a.m. each day
  • More than 75 performing artists including Florence + The Machine, My Morning Jacket, Jane’s Addiction and more
  • Single-day tickets and three-day passes are available on the Shaky Knees site

You definitely will get weak in the knees upon seeing the lineup at this year’s Shaky Knees Music Fest (anyone else stoked that Huey Lewis and the News is performing?)! This is one of Atlanta’s biggest music events, and the party continues to get better each year since its 2013 inception. In addition to the main lineup at Centennial Park, Shaky Knees offers some smaller, late-night shows at various venues throughout the city (which require separate tickets in addition to regular festival passes). Since all that dancing will build up an appetite, festivalgoers can get some great noshes at our favorite Atlanta food trucks, as well as others from around the Southeast.

What to wear: In between sets and when you need a break from the tunes, show off your stylish duds from Edgewood’s Sole Shoes & Accessories. (Don’t let the name fool you; they have tons of cute clothes!) We went with outfits that would do well in the warm outdoors and especially focused on footwear since the ground can get kind of grody at music festivals (plus, you’re standing on your feet for most of the day). Sole is a great boutique to create the perfect outfit because they literally carry everything you’ll need, head to toe.

Look #1:


From Sole Shoes & Accessories: Microsuede camel racerback tank, $55; Tencel sky-blue shorts, $60; sneakers, $89; hat, $62; beaded meditation necklace, $90

Look #2:


From Sole Shoes & Accessories: Print romper, $45; snake cuff, $90; laser cutout gladiator sandals, $153; turquoise crossbody, $98

Look #3:


From Sole Shoes & Accessories: Plaid green shirtdress, $54; Matt & Nat crossbody, $142; platform sandals, $105; vintage sunglasses, $25


We loved all of Sole’s accessories, but that snake cuff is super cool to add to your summer wardrobe.

The Event: Atlanta Jazz Festival

  • Friday, May 27, 2016, through Sunday, May 29, 2016
  • Free and open to the public at Piedmont Park
  • Jazz-related events happen throughout May, leading up to the outdoor festival, so check the schedule online.

Celebrate Memorial Day weekend with jazz. Lots of jazz. In fact, why you don’t you celebrate the entire month of May with jazz, as the Atlanta Jazz Festival offers music-related events every single day of the month, culminating in a star-studded, weekend-long, outdoor festival at Piedmont Park. Featured performers include Gregory Porter, The Benny Golson Quartet, Elaine Elias and many more (the full schedule is online). If you prefer your jazz in a sleek, late-night setting, walk over to Park Tavern for a more intimate, contemporary jazz concert Saturday night (tickets are $35 in advance; $40 at the door).

What to wear: Because the Atlanta Jazz Festival is one of the largest free jazz festivals in the country, you need to look good at the event (and since you’re saving money on attendance fees, you can roll that money back into your prospective ensembles). We visited Tootsies to offer three ideas on what to wear to this jazzy event. Since customer service and personalized attention, in addition to stylish merchandise, are such cornerstones at this Buckhead boutique, we had three Tootsies stylists each create his or her own look for the event.

Look #1 (“boho chic” by stylist Anthony Walega):


From Tootsies: Tropical maxi dress, $355; embossed leather crossbody, $250; white-jeweled sandals, $540; parrot bracelet, $285

Look #2 (“classic style” by stylist Sara Wolf Mixon):


From Tootsies: Meringue blouse tank, $225; striped pleated shorts, $300; gold flats, $495; gold glass necklace, $1,850; linen tote, $550

Look #3 (“artsy edge” by stylist Maya Kight):


From Tootsies: Elizabeth + James racerback dress, $365; black gladiator sandals, $445; slate studded crossbody, $650; cat-eye sunglasses, $360


A close-up of the wonderful accessories we shot at Tootsies. I’m already saving up for that lovely gold glass necklace!

Whether you’re an art collector, die-hard music fan, nature enthusiast or a cool chick who fits somewhere in between, May is definitely your month to have fun with fashion in the lovely outdoor weather.


Guess what! We’re heading to Charlotte, NC, this spring! Yep, we’re launching StyleBlueprint Charlotte, and you can be among the first to know when we’re live. Click here to sign up!

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