Cup Day

Fashions on the Field – Saturday 1st May 2021

The Fashions on the Field will be held on the trackside stage on the front lawn (out the front of the Ted McCabe Building) at Hawkesbury Race Club, Racecourse Rd, Clarendon NSW 2756 on Saturday 1st May 2021 at 2pm. You must be present by 2pm for a 2:15pm start* (*timings may vary slightly due to race times on the day).

There will be 2 categories: Best Dressed Lady and Best Dressed Gentleman.

The Fashions on the Field will be run in a traditional style with heats and a final. Finalists will be chosen from the heats and the final will be run directly after the heats. The number of heats will be determined by the number of entrants on the day.

Winners will be announced on the day and must agree to be photographed after the event.


Please read about the event below and if you would like to register, please email: with your full name and your registration for either the Best Dressed Lady or the Best Dressed Gentleman category. Please ensure you have read and unsterdtand the T&Cs.

Fashions on the field is a free event however you must have a ticket for the Gold Cup Race Day or you can purchase a ticket for the race day at the gate on the day.



Best Dressed Lady

Judges are looking for a standout traditional racewear look from head to toe and something they haven’t seen before


Best Dressed Gentleman 



Stacey Hemera Roberts, Milliner

Stacey is a rising hat designer and avid supporter of races fashion. Not one to shy away from pushing the boundaries, Stacey loves to showcase her creativity through the art of dressing. With an eye for current trends and fashion; by popular demand her passion has naturally evolved into her designing and making hats for others.         

Her millinery design style is clean and sleek with a focus on shape, brims becoming her signature. Every piece is hand-crafted out of her home studio in the Hawkesbury, NSW.

Social Media: Instagram: @designsbyshr @designsbyshr @staceyhemeraroberts


Leena Thompson, Celebrity Stylist 

Celebrity Fashion stylist Leena Thompson has had a 15 year fashion career styling many local and international celebrities. She has styled runway shows and photo shoots. 

Leena’s motto is:  “It’s how you wear fashion not what you wear” 

Leena has judged numerous Fashions on the Field Competitions including Myer at Randwick on Derby Day and Queen Elizabeth Stakes Day, Golden slipper at Rosehill and the Blue Diamond at Caulfield 

Leena has worked her magic and created outstanding race wear looks for Emma Booth, Jessica McNamee, Renee Bargh, Tiarnie Coupland, Tammin Sursok, Sophie Hensoir, Natalie Roser, Monika Radulovic, Cherry Cassidy, Megan Gale and Firass Durani 

Leena will be looking for men and women who can pull off an amazing spring race wear look.  She wants to see colour and coordination from hairdo to shoes and the right balance of the outfit. 

Social Media: Instagram: @leena_thompson @styledbyleena


Rob Lee, Winner of the HRC Fashions on the Field 2020

Rob is originally from Chicago, IL USA and currently works in the financial markets for ABN Amro in Sydney. He came to Australia in 2014 with his wife, native Australian and milliner, Kathryn. In 2017 Rob and Kathryn opened Love Lee Boutique, a women's boutique showcasing Kathryn's millinery, racing fashion and accessories. 

Rob has impeccable style and has been participating in Fashions on the Field since 2014 and won the Hawkesbury Saddle Up for Spring Fashions on the Field in 2020. Rob enjoys competing in Sydney and at racing clubs around Australia.

Social Media: Instagram: @love_lee_boutique and @rwlee33




Prize pool value approximately $6000

Best Dressed Lady

Race wear for women should be conservative and covered, usually a tailored dress or skirt, or a feminine suit styled with an autumn hat or headpiece. The Best Dressed lady will be beautifully styled with thought put into their shoe and accessories choices as well as having an understanding of the trends for the season. Grooming, deportment and personal style will also come into play when the judges decide on the look.

1st Prize: 



Instagram: @designsbyshr


     Instagram: @leena_thompson @styledbyleena


Instagram: @clareoharaart


Instagram: @yprsydney


Instagram: @hillsandwest


Instagram: @nikisimpsonhairandmakeup


Instagram: @heysousou


Instagram: @thestyledr


Instagram: @the_shared_attelier


Instagram @wildbunchflorist


Runner Up

Instagram: @thestyledr


Instagram @wildbunchflorist


Best Dressed Gentleman

The Best Dressed Gentleman should epitomise style. A tailored suit with a great shirt and tie combination is a must.  Attention to detail will also be considered when deciding the winner so make sure you have thought about your shoes, cufflinks, a pocket square, a watch, men’s accessories and of course a hat. 

1st Prize: 

Instagram: @academybrand 



Instagram: @craigmoorwines 

Instagram: @robertoatleywines


Instagram: @hillsandwest


Instagram: @clareoharaart


Instagram: yprsydney


Runner Up

Instagram: @academybrand