The Westport library was transformed from a sanctuary of literature to a glamorous, dimly-lit haven of high fashion on Saturday, March 4, for Westport’s third annual Fashionably Westport event. Townspeople of all ages gathered to cheer on friends and family as they rocked the runway, dressed by local Westport retailers, to support the Fairfield County charity Homes with Hope. 

  The Westport Downtown Association (WDA) partnered with the Westport library and a plethora of local shops and sponsors to host the event. Jill Dunn, the Events Director for the WDA, spearheaded the planning of the event. 

“A lot goes into organizing an event of this size,” she said. “Everything from insurance, to coordinating the vendors, to the catering—even the bar donations. There are a million moving pieces.” 

The WDA begins brainstorming for the event about six months in advance. It takes Dunn and her associates about three to four months for the event to fully come together.

Dunn worked closely with Emma Rojas ’18 to coordinate vendors, sponsors and models. Rojas, the former Marketing Director for the WDA, has been involved with Fashionably Westport since its creation three years ago. 

The fashion show featured items from 20 local stores, with over 40 Westporters acting as models. Weston resident and influencer, Amy Guzzi, served as the runway director, communicating between the vendors and models. The fashion show was emceed by local comedian Courtney Davis.

In addition to the fashion show, attendees of the event had the opportunity to shop and eat locally, with many Connecticut boutiques and eateries holding pop-up shops at the event. Terri Jaffe, co-founder of Westport-based e-commerce site DuxStyle, was just one of many business owners to participate in the event. 

“As Westport residents and business owners, [my partner and I] strongly believe in shopping locally, and thus, we wanted to sponsor Fashionably Westport to show our support for the Westport Downtown Association,” Jaffe said. 

Though a fun way to spend a Saturday evening, Fashionably Westport, is, at its core, a philanthropic event. Katharine Murray, marketing manager of Homes with Hope, explains that the proceeds from Fashionably Westport will go towards helping Homes with Hope achieve their goal of preventing and ending homelessness in Fairfield County, through the funding of homeless shelters, food pantries and housing services.

 “Homes with Hope is so grateful to be the official sponsor of Fashionably Westport,” Murray said. “It’s amazing to see the overwhelming community support for our cause.” 

Last year, the WDA raised $5,000 for Homes with Hope. This year, Dunn, Rojas and their team hope to double that total. 

“The most rewarding part of the event is seeing how happy and grateful the representatives from Homes with Hope are,” Rojas said. “At the end of the day, Fashionably Westport is an event for charity and [the WDA] couldn’t be more excited to raise money for them.”