Westport, CT

Winged Monkey

Prom gowns from corset bodices to ball gowns on Post Road East, and no occasion needs an appointment

Woman-owned

A prom dress usually starts as a picture in someone’s head, maybe a corset bodice, a front slit or a full ball gown, and the Winged Monkey prom collection covers those shapes, in metallics, florals, neutrals, black, white and a run of brights from purple to orange.

Winged Monkey is a women-owned shop that dresses girls and women in everything from jeans and swimwear to gowns, but the store is clear that special occasion dresses and gowns are the specialty, and prom has its own collection with seasonal sub-collections. There is no appointment system to work around. The store answers the question directly: “You do not need an appointment for any occasion.”

The prom racks on Post Road East

The labels attached to the boutique’s prom collection are a familiar list for anyone who has shopped a spring season in lower Fairfield County, Connecticut, and the collection mixes the big beaded-gown houses with contemporary labels better known for cocktail and wedding guest dresses.

Deepest groups in the collection

Filling in the rest

  • Atria
  • Chandalier
  • Katie May
  • Shona Joy
  • LIIS
  • Nookie

Alyce Paris shows up in the formal and homecoming sections as well.

If the size or color you want is not in the shop, the boutique can place a special order, and staff are happy to help with sizing questions before you come in. A first-time prom shopper who has never worn a structured gown gets the most out of that offer. Asking how a particular label runs is a quick phone call that can save a lot of trying on.

For Staples High School students, Winged Monkey is a hometown option on Westport’s stretch of the Post Road, which is US 1, east of the downtown shops along the Saugatuck. Fairfield Ludlowe and Fairfield Warde sit to the east, Weston High and Wilton High to the north, and Norwalk High and Brien McMahon to the west, so the shop sits among several districts’ prom calendars at once.

Beyond prom at Winged Monkey

The formalwear side adds communion and flower girl dresses and bridesmaid styles.

  • Juniors and preteen

    The middle school dances that come before prom

  • Bat mitzvah

    Party and service dresses

  • Girls’ department

    Size 2 through 16, for a younger sister on the same visit

Everyday clothing, shoes and accessories take up the remaining floor space, which is handy when a prom outfit still needs a clutch or a pair of heels.

We specialize in special occasion dresses and gowns - so whatever the occasion, we have the dress for you!

Winged Monkey closes its short description of itself with that promise, and prom is the occasion with the biggest share of the formalwear side.

Winged Monkey in Westport: a quick answer

What if my size is sold out?

Ask about a special order. The store can bring in a size or color it does not have in stock.