We’re only days away from the magical time of year that every Memphian looks forward to: Memphis in May. Whether you’re headed to Beale Street Music Festival, World Championship Barbecue Cooking Contest or celebrating the city of Memphis at 901Fest, there’s an event for every interest. And you’ll definitely want to stop by the Jockeys & Juleps Derby Party at Southern Reins, Art by Design at the Pipkin Building and Botanical Bars at Memphis Botanic Garden.

May’s edition of What to Wear features models who all support the local event, Art By Design. Aisha Raison, local filmmaker and photographer; David Quarles IV, designer of IV By David jewelry and partner at Stock & Belle; and Colleen Canale, wife of Chris Canale, who owns Old Dominick Distillery (aka the backdrop for this month’s photo shoot). These models rocked looks from Oak Hall, Dazzle, James GattasStock & Belle and Lansky 126, as well as Derby hats from Makowsky Millinery, all of which were created by stylist Cara Grinder. Take a look at what to wear this month!

The Event: Jockeys & Juleps Derby Party at Southern Reins Equine Therapy

  • May 4, 2019
  • 3 p.m. to 7 p.m.
  • $150 to $200 per ticket
  • For more information visit, southernreins.org.

This year’s Jockeys & Juleps party, held at Southern Reins Equine Therapy, will feature live music, a bourbon bar, Derby desserts, a live auction and raffle, a hat contest and more, in an event you won’t want to miss. It’s truly the next best thing to attending the 2019 Kentucky Derby in person.

What to wear: For the ladies, don your best dress and Derby hat. And for the gents, a tailored suit and snappy tie is the only way to go.

Our models are stunning in their beautiful dresses and handsome suits.
Jockeys & Juleps Derby Party is the perfect time to throw on your best dress and hat!

Look #1: 

Colleen is looking stunning in her spring colors for Jockeys & Juleps Derby Party!
Colleen’s look from Oak Hall: Dress, $565 | From Dazzle: Shiver + Duke earrings, $68; Hammitt clutch, $185 | From Makowsky Millinery: Pink hat, $299
We are loving these details.
These Shiver + Duke earrings from Dazzle are absolutely stunning with spring colors!

Look #2: 

Perfect for spring, we are loving this floral tie with the chambray color!
David’s look from Stock & Belle: Chambray blue jacket, $200; chambray blue pants, $100; button-down shirt, $80; floral tie, $60

Look #3: 

Keeping it simple with the navy, this two-piece dress is a great choice for the Jockeys & Juleps Derby Party!
Aisha’s look from Oak Hall: One-piece dress, $1,295 | From James Gattas: Evocateur earrings, $170; Evocateur necklace, $250 | From Makowsky Millinery: Fascinator, $149
We are loving this stunning set!
This matching set from James Gattas adds just the right amount of color to this look.

RELATED: Local Singer-Songwriter Liz Brasher Performs at Beale Street Music Fest

The Event: Art By Design at The Pipkin Building

  • May 8-12
  • Various times
  • $20 to $250 per ticket, depending on the event
  • For more information visit, artsmemphis.org.

More than a dozen designers create custom vignettes inside a chic gallery showroom at this design-centric event. Attendees all across the Mid-South come to experience this unique collaboration by attending an event and touring the showroom at the Pipkin Building. Events include cocktails and floral arranging, a seated dinner prepared by Chef Ryan Trimm, “Mingle and Mimosas,” Ferguson’s Cocktail Party and more. Find a complete line-up at artsmemphis.org.

What to wear: Even though this is a casual event, we encourage you to wear something floral and bright, or anything that expresses your inner creativity. Our recommendation? A fun top and jeans, plus a pair of wedges or heels that bring your outfit to life.

Look #1: 

We are loving this entire colorful set that's perfect for spring!
Colleen’s look from Oak Hall: Striped jacket, $575; striped shorts, $325 | From Dazzle: Yochi earrings, $63; Uashmam bag, $119
It's all in the details with this beautiful romper set!
From James Gattas: Dove 18-karat diamond fashion ring, $2,400

Look #2:

We are loving the colors in this floral dress shirt!
On David from Stock & Belle: Floral shirt, $80; Navy pants, $100

Look #3:

This sheer and colorful top is great for Arts By Design!
Aisha’s look from Lansky 126: Sheer top, $115 | From Oak Hall: White jeans, $198
We are loving these colorful earrings from James Gattas!
James Gattas: Evocateur earrings, $170

RELATED: Only in Memphis: 10 Things That Make Us What We Are

The Event: Botanical Bars at Memphis Botanic Garden

  • May 30, 2019
  • 6 p.m. to 8:30 p.m.
  • $30 for MBG members; $40 for nonmembers
  • For more information visit, memphisbotanicgarden.com.

Beginning in May, the Memphis Botanic Garden will host four Botanical Bars events and introduce attendees to the plants that add that hint of flavor to their favorite cocktails. The theme for May 30 is “Herbal Highballs,” and guests will have the opportunity to sip their way through the stunning gardens. Stop by the gin and tonic bar to create your own custom drink, or enjoy bubbles and blossoms with a lavender-peach bellini, cucumber-mint cocktail or local brews.

What to wear: Since this is an outdoor event, dress casual and comfy. This can mean a romper set, flare jeans and a cute top, or just a simple dress!

We are loving this entire color scheme that is the perfect shade for summertime outfits.
Our fabulous models are ready to sip on delicious drinks and eats at Botanical Bars!

Look #1: 

Colleen is ready to enjoy some drinks and eats at Botanical Bars!
Colleen’s look from Oak Hall: Floral top, $295; Rag & Bone belt, $225 | Jeans are model’s own.
Pair these classy and elegant pieces together to create a statement!
From James Gattas: Dove 18-karat yellow-gold and white onyx diamond pendant necklace, $2,400; 14-karat long hammered disc necklace, $1,299

Look #2: 

Perfectly floral for spring and summer, we love this entire look!
David’s look from Stock & Belle: Floral shirt, $85; green pants, $60

Look #3:

We love this two-piece set that Aisha is rocking!
Aisha’s look from Stock & Belle: Orange top, $68; orange pants, $98 | From Dazzle: Street Level handbag, $59.50; Betsy Pittard earrings, $44
These colorful details make her entire outfit the perfect one for warm weather!
From Dazzle: Betsy Pittard earrings, $44
We are loving these colorful bangles!
From James Gattas: Evocateur bangles ranging from $165 to $330; bamboo 14-karat gold bracelet, $1,990

Here’s to a wonderful and eventful May season!

Thank you to Elizabeth Looney for the fabulous photos at Old Dominick Distillery!  

We love the rooftop at Old Dominick Distillery!
Thank you to Old Dominick Distillery for letting us shoot at your fantastic venue!


For more on what’s going on in Memphis this month, visit our Happenings page. And for more on the boutiques that provided these style suggestions, visit our SB Guide or download our FREE SB App.

About the Author
Katelyn Caughron

Katelyn is the Client Relations & Social Media Coordinator for StyleBlueprint. She loves fitness, the Memphis Tigers, and a good brunch.