Anna Leigh Waters wearing a red and white checkerboard outfit.
Anna Leigh Waters at the Veolia Chicago Cup. PPA Tour

Best dressed at the Veolia Chicago Cup

The fashion competition was fierce at the Veolia Chicago Cup.

While familiar favorites continued to set the standard, a few fresh faces made their debut on the Best Dressed List.

Here are the best dressed pros from the tournament.

Sofia Sewing and Jorja Johnson

Sewing and Johnson wearing black and white dresses
Sofia Sewing and Jorja Johnson at the Veolia Chicago Cup. PPA Tour

Can Sewing and Johnson make women’s doubles a regular thing? If it means more iconic coordinated looks like this, absolutely. The duo struck the perfect balance between matching and individuality in black-and-white ensembles that showed off their distinct styles. Sewing opted for a black wrap dress with a tie and torso cutout from Beach Riot, while Johnson went with a fitted black bubble-hem dress from Berlook, topped off with an oversized hair bow. The finishing touch? Matching white piping on both little black dresses, taking their courtside coordination to another level.

Hurricane Tyra Black

Black in a blue and cream twirly dress
Hurricane Tyra Black at the Veolia Chicago Cup. PPA Tour

Some on-court looks make me want to add them to my closet immediately, and this navy blue Wilson dress worn by Black in mixed doubles is firmly in that category. The cream seams create a gorgeous, figure-flattering silhouette, while the extra paneling in the skirt adds beautiful movement. This might just be one of my favorite dresses of the season. Absolutely stunning.

Pablo Tellez

Tellez wearing a light blue shirt with matching navy shorts
Pablo Tellez at the Veolia Chicago Cup. PPA Tour

Tellez made a strong case for a back-to-back appearance on the Best Dressed List with another standout look from Joma. The turquoise and navy color combination is a winner, but it’s the attention to detail that takes this outfit to the next level. Tellez paired the set with black Joma court shoes and a bright green sweatband that perfectly matched the accents on his shoes. Another stylish showing from the men’s side of the tour.

CJ Klinger and Kiora Kunimoto

Klinger in a blue outfit with red sleeves, and Kunimoto in a red dress
CJ Klinger and Kiora Kunimoto at the Veolia Chicago Cup. PPA Tour

We have a new face on the Best Dressed List: CJ Klinger. And he may have his mixed doubles partner, Kiora Kunimoto, to thank for the stylish debut. A regular on this list, Kunimoto brought the color in a vibrant red 11NIL dress paired with white court shoes. Klinger picked up on her color scheme, incorporating red compression sleeves from SParms, Pilla glasses and a matching paddle. He finished the look with a blue Adidas shirt and black accessories. If this is the kind of coordinated style we can expect from Klinger and Kunimoto, we may have a new best-dressed mixed doubles duo on our hands.

Jack Sock

Sock wearing a red and white outfit
Jack Sock at the Veolia Chicago Cup. PPA Tour

Jack Sock is another newcomer to the Chicago Cup’s Best Dressed List, and his latest look is a winner from head to toe. Known for keeping his court style simple, Sock added a pop of personality with a cherry-red ensemble featuring a matching T-shirt and court shoes, crisp white shorts, crew socks and a white hat. Even his red-and-white Selkirk paddle fit the color scheme perfectly. Sometimes, keeping it simple is the ultimate style play.

Chris Haworth

Haworth wearing blue
Chris Haworth at the Veolia Chicago Cup. PPA Tour

Haworth is starting to experiment a little more with his on-court style, and this blue Skechers set was my favorite look of his from the weekend. The ombre blue tee is a fantastic color on him, and he nailed the styling with coordinated white-and-blue accessories and matching Skechers court shoes. It's a fresh, polished look that proves a little color coordination goes a long way.

Keilly Ulery

Ulery in a red dress
Keilly Ulery at the Veolia Chicago Cup. PPA Tour

Our final newcomer to this week’s list is Keilly Ulery, who made a stunning debut in a burgundy tiered dress from POPFLEX Active. Between the structured bodice, delicate mesh overlay on the skirt and rich burgundy hue, there’s plenty to love about this look. Ulery kept the styling simple with white Diadem court shoes and a tan Adidas visor, letting the dress take center stage as she hit the court for singles. What a way to make a first impression!

Anna Leigh Waters

Waters wearing a red checkerboard patterned outfit
Anna Leigh Waters at the Veolia Chicago Cup. PPA Tour

Waters celebrated her 200th career title in style, debuting a new Nike look that was an instant favorite. The red-and-white gingham set she wore in singles brought a playful, preppy vibe to the court, and the matching red visor and court shoes tied everything together. A historic milestone deserves an equally memorable outfit, and Waters delivered on both fronts.

Honorable mention: Leigh Waters

Waters family after Anna Leigh's 200th title win
Leigh Waters, Anna Leigh Waters, and Stephen Waters at the Veolia Chicago Cup. PPA Tour

Of course, Mama Waters was courtside looking as chic as ever for her daughter’s 200th title celebration. Leigh Waters coordinated beautifully with Anna Leigh’s red-and-white gingham look, adding her own twist with bright blue-and-white floral Nike track pants. The bold floral print made a statement, earning the courtside coach standout style points on a historic day.

What was your favorite look from Chicago? Let us know on Instagram.