Photography by Tara Noelle

Greenwood Stakes 2019: The Best Looks at the Races

Because horse racing and extravagant outfits always go hand in hand.

Date May 27, 2019

The sun came out just in time for the second annual Greenwood Stakes, as partygoers arrived decked out in their finest race gear. Bowties, ascots and vests proved popular among the gentlemen in the crowd, while women stood out in statement hats, fascinators and colourful cocktail dresses. Daytime dressing was elevated to a whole new level with outfits that were off to the the races — both literally and figuratively.

The stylish crowd sipped cocktails made by mixologists from Figo, Bar Raval and Chantecler while they mingled between races in Woodbine’s new Trackside Clubhouse. On the patio only feet from the racetrack guests got a exclusive view of the Greenwood Stakes and Marine Stakes and inside the clubhouse the entertainment continued with DJ sets, an acoustic performance and a pop-up art gallery.

Excitement peaked as Jay Cheng of Jaycow Millinery led a hat parade showcasing her designs to the central stage where the Style Stakes winners were announced by FASHION Magazine’s fashion editor, Eliza Grossman. Throughout the day, Style Stakes judges nominated men and women with the most fashionable looks to be eligible for a $500 cash prize and the title of Belle Du Jour and Gallant Sartorialist. The this years winner’s were Edweina Saurin and Bismark Adomako. The pair impressed their judges with their sleek and stylish looks and will be invited back next year to sit on the judging panel.

Click through to see our favourite looks from the 2019 Greenwood Stakes.