Winged Monkey Westport: Elevated Formal Wear for Every Celebration
Since its founding, Winged Monkey in Westport has been the usual first stop for anyone seeking sophisticated formal wear. Located on Post Road East in this charming Fairfield County town, the boutique caters to customers shopping for proms, weddings, mother-of-the-bride events, and other special occasions that demand composure and style.
Westport’s position as one of Connecticut’s most affluent and culturally energetic communities makes it the perfect home for an upscale boutique like Winged Monkey. Students from Staples High School, one of the state’s highest-ranked public schools, often make the trip here to find their prom dresses. The boutique sits near historic Post Road landmarks and shopping areas that have made this stretch of Westport a retail destination for decades.
Extensive Formal Wear Departments
The store’s formal wear selection is truly comprehensive. Winged Monkey maintains a dedicated department featuring prom gowns, mother-of-the-bride and mother-of-the-groom styles, bridesmaids dresses, flower girl options, and guest-of-wedding attire. This breadth means your entire family can find coordinated looks from a single trusted source.
Beyond dresses, the boutique stocks accessories, jewelry, and shoes that complete your formal ensemble. The professional fitting and alterations services ensure your chosen dress fits like it was made specifically for you.
Services That Go Beyond the Sale
Winged Monkey doesn’t simply sell dresses and say goodbye. The team offers steaming, gown cleaning, and preservation services, protecting your investment for years to come. Tuxedo rental and sales are also available, making this a true one-stop shop for formal events.
Attendees of a spring prom, a summer wedding, or any formal celebration, the extended hours (open six days a week, including evening appointments) mean you can shop on your schedule.
| Service | Details |
| Bridal | Wedding gowns with dedicated bridal suite experience |
| Bridesmaids | Full selection of styles and colors for wedding parties |
| Prom | Designer prom gowns from Faviana, Jovani, La Femme |
| Alterations | In-house tailoring and fitting services |
| Accessories | Jewelry, shoes, and finishing touches for any occasion |
The customer who shows up after six isn’t always a student. Westport has a meaningful share of working professionals who need a cocktail dress for a Manhattan event and don’t have a lunch break to spare, and Winged Monkey’s evening hours are aimed as much at them as at high school juniors. The floor is merchandised so both shoppers can find what they need without being steered down the same rack.
Westport as a town has a particular aesthetic preference that’s less about trend-chasing and more about quiet quality, and the floor reflects that. Oversized labels are kept to a minimum, and the staff doesn’t lean on designer names to close a sale. That confidence in the inventory itself, rather than the branding attached to it, is what a longtime Westport customer tends to describe when explaining why they keep coming back.
Does the boutique offer tuxedo rentals?
Yes, Winged Monkey carries both tuxedo rentals and sales, making it possible to outfit your entire group for formal events in one location.
Can the boutique preserve my wedding gown after the wedding?
Absolutely. Professional preservation services protect your gown from yellowing and damage, keeping it beautiful for decades.
What should I bring to my fitting appointment?
Bring any shoes you plan to wear, as heel height affects dress length. Many customers also bring photos or inspiration images to discuss style preferences with the fitting specialists.