Woollahra Festival 2025
Woollahra Village Fashion & Lifestyle Day
Thursday 16 October 2025
Celebrate style, elegance and community along Queen Street, Woollahra at the
Woollahra Village Fashion & Lifestyle Day
The business community of Queen St, Woollahra are celebrating everything that is special about Woollahra Village in association with the Queen Street & West Woollahra Association.
The charming streets of Woollahra are set to come alive with fashion, style, music and events at the Woollahra Village Fashion and Lifestyle Day on Thursday 16 October. Set against the backdrop of the iconic Queen Street, one of Sydney’s most elegant retail and lifestyle destinations, the day promises a vibrant celebration of this special destination, join the community and explore the beautiful stores and make your way to events around the Village.
Woollahra Village Fashion Show
Thursday 16th October 2025 | 11.30am for a 12pm show
The major event of the day will be a Fashion Show at the Woollahra Hotel, the first floor and terrace will be transformed into a beautiful salon by Creative Director, Grant Pearce, Editor in Chief, Esquire Australia. The runway will showcase the latest designer collections curated by David Heimann, Orson & Blake Consutancy. On show will be men ‘s and women’s fashion from Queen Street’s premier fashion boutiques including Moss & Spy, Aquel, Reads Woollahra, Cable Melbourne, MJ Bale and Riada Concept. There will also be a children’s fashion component from the renowned Monogram Mode.
The show will feature designs from leading local and sought after international labels, offering a unique glimpse into the season’s most coveted trends – right where they are available and ready to purchase in Woollahra Village boutiques and flagship stores.
All show attendees will receive a complimentary gift bag, filled with fabulous items from local stores and businesses, along with a glass of champagne and ribbon sandwiches following the show.
Tickets are $79 each. Book here to reserve your place. 
Bistro Moncur Luncheon with Maureen Jordan, Harper’s Bazaar, Australia
Thursday 16th October 2025 | 1 pm for a 1.15 sharp seating
Make sure you book your seat for lunch at Bistro Moncur with guest speaker Maureen Jordan, publisher of Harper’s Bazaar Australia & Esquire Australia. In conversation with Nicole Abadee, you will learn more about Maureen’s life and career and how she became involved in the fashion and lifestyle publishing industry. Celebrated chef Tom Deadman will be serving a 2 course lunch menu which honours the legacy of Bistro Moncur’s hero dishes plus petits fours. Complemented with matching wines. Single tickets will be available as seating will be banqueting style.
Tickets are $149. Book here now.
“If these hands could speak”
Talk by Anne Schofield A.M.
Anne Schofield
Meet Anne Schofield in her beautiful jewellery store in the historic building The Bond.
Renowned antique jewellery expert Anne Schofield AM will take you on a journey as she talks about her 57 years in Queen Street; her love of jewellery, her career as an antique dealer, historian and consultant at her bespoke Queen Street store. Anne has been in business in Queen St since 1968 and holds many special memories and wonderful stories to reveal. Not to be missed.
Tickets are $59 each and include a free copy of Anne’s book ‘Australian Jewellery, 19th and Early 20th Century’, valued at $125. Book now, places are limited.
In Conversation: Tim Olsen & Peter Switzer
Tim Olsen
Peter Switzer
Join Tim Olsen and Peter Switzer in their lively and uncompromising conversation about money and art! Be delighted by their bravado as they reveal the challenges they face in the world of art and finance.
Discover how they see the evolution of a new world order.
“When Switzer meets Olsen” will be an exciting and inspiring dialogue between two experts who share their obstacles and dreams in the respective fields they operate.
Book your tickets here. Free but Numbers Strictly Limited.
Queen Street is renowned for its heritage charm and curated retail experience, where visitors can explore the fashion boutiques, homewares stores and artisanal goods, while enjoying gourmet food throughout the village’s restaurants and cafes, making it a must-visit destination for lovers of luxury, design and lifestyle.
Beyond the fashion show, guests can enjoy lifestyle events taking place throughout the day, including:
The Woollahra Fashion and Lifestyle Day is the perfect opportunity for Sydneysiders and visitors alike to discover the timeless appeal of Queen Street.
The Woollahra Village Fashion & Lifestyle Day is sponsored by the following major sponsors:
© Woollahra Festival 2025
Website design by Aspen PC Projects 2025
Woollahra Council acknowledges that we are on the land of the Gadigal and Birrabirragal people, the Traditional Custodians of the land. We pay our respects to Elders past, present and emerging.