Join Our Vineyard Community 

Hi, I’m Ashley! The person behind the hats.

I originally started designing these as a fun way to build a little more community around our island life and the work we do every day. Real estate can be serious business, but it’s also about relationships, personality, and the lifestyle that makes people fall in love with this place.

The idea for the hats came from wanting something simple, classic, and wearable — something you’d actually throw on for a beach walk, a showing, or a coffee run in town.

Every piece was designed with that in mind: clean, timeless, and easy to wear anywhere on the island.

Thanks for supporting the idea and helping turn a small creative project into something bigger.

At Portfolio Properties, we’re more than a brokerage, we’re a community. From Chappy to Vineyard Haven, we host events, celebrate local culture, and share exclusive experiences with our clients and friends. Our limited edition hats are a way to join the fun and show your Vineyard pride.

  • Premium quality materials and embroidery
  • Comfortable, adjustable sizing for all 
  •  Vineyard-inspired designs unique to our brokerage 
  • Limited editions for exclusive style

Item A778: Premium Navy Adjustable Hat - Slip Jack Canvas Leather Strap Hat with Adjustable Fit Embroidered with Martha's Vineyard Down East style Lobster boat in Blue

Item A779: Premium Navy Adjustable Hat - Slip Jack Canvas Leather Strap Hat with Adjustable Fit Embroidered with Martha's Vineyard Down East style Lobster boat in White

Item A780: Richardson Six-Panel Adjustable Snap Back - Trucker cap, 60% cotton Patched with Martha's Vineyard Down East style Lobster boat in White. Perfect for the office, the beach, or weekend adventures.

Sign Up & Claim Your Hat

Connect, explore, and represent our brokerage lifestyle with limited edition hats 

Ready to get your gear? Fill out the form below to reserve your items. Our team will follow up to confirm details. Fields: Name, Email, Phone Number

“Love my navy hat – perfect fit and high quality!” – Brendan K.., Client
“These hats make me proud to represent our brokerage!” – Agent