Dress up with a Dreamboat

Two sisters create elegant and entertaining hats for the Kentucky Derby.


Since 2016, Islanders have gathered at the Harbor View Hotel to watch the Kentucky Derby. Vehement follower or not, it’s an excuse to dress up, go out, eat, drink, and maybe win some money on a Saturday afternoon. It’s a big day for horses, and perhaps just as big of a day for hats. Islanders Tania Tilton and Stephanie Rossi look forward to it every year.

“My three favorite things are horses, hats, and bourbon,” Tilton said while sitting at her living room table in her Edgartown home. Printed pieces of colorful fabric covered the table’s surface, and dozens of hats hung on display to the left of the front door.

Tilton’s Edgartown home doubles as a studio and retail shop for Dreamboat Hats, a homemade hat, bow tie, and pocket square company founded by Tilton and Rossi, sisters and 12th generation Islanders. They’ve been crafters and artists all their lives, but the business came to fruition just one year ago.

“She’s the crafty one,” Tilton said of her sister.

“She has all the ideas,” Rossi added.

The duo create wide-brimmed hats, sun hats, fascinators, headbands, clips, boaters, bow ties, pocket squares, and essentially anything else upon request. They all come in different shapes, sizes, colors, and materials.

Many Islanders sport Dreamboat Designs at events like the Kentucky Derby party, Fourth of July Parade, St. Patrick’s Day Parade, and the Taste of the VIneyard. Their shop is open by appointment, and they’re holding a trunk show at the Harbor View from 11 am to 3 pm on Saturday, May 5, before Saturday’s Kentucky Derby party.

With over 50 hats in stock, there’s a style for everyone. Some have dramatic displays of roses, lilies, sunflowers, and pheasant feathers, and others are minimal, with just a ribbon, an antique button, or a touch of bling.

“That’s her trademark,” Rossi said of Tilton. Tilton loves adding a small sparkling gem to the brim or base of the hats.

The sisters are self-taught. They researched, watched tutorials, and learned through trial and error. Sinamay is a popular and lightweight hat-making material. Rossi and Tilton order the sinamay online; it comes in a big roll of material. Rossi sews and forms the material to take shape of the desired design, which can take a couple of hours, depending on what she’s making. Sometimes they buy blanks — plain, simple, untouched hats — and then add their own flair.

Clips, fascinators, and headbands range from $15 to $45, hats are $25 to $75, and bow ties are $40. The bow ties are 100 percent cotton, and come in just about any print imaginable. Rossi does all the sewing.

Two Dreamboat hats were down in Louisville for last year’s Kentucky Derby race. The niece of the owner of Irish War Cry, a competing horse in 2017, comes to the Vineyard, and heard about Dreamboat’s elegant, handmade hats. She visited the Edgartown shop and picked one out. Tilton’s neighbor also went to the Kentucky Derby last year. She brought over her dress, and Tilton and Rossi custom-created a hat to match it — something they love to do. Derby hats in Kentucky can cost up to $1,000, according to Tilton. She fulfilled a lifelong dream and went to the Derby herself a couple of years ago.

This isn’t Great Britain, and big hats haven’t quite hit our market in the way Tilton and Rossi wish they would. They encourage women to get out of their comfort zones and wear hats.

Dreamboat means beautiful, and that’s where the name of their business was inspired. They also wanted it to have a nautical, Edgartown-feel.

“They make you feel fancy and taller,” Rossi said. “And you can never have a bad hair day.”


For more information on Dreamboat Hats, call 508-627-0409, or email dreamboathats@outlook.com.