Flannels, thermals, muck boots, and puffy coats – the Vineyard doesn’t have a reputation for
being fashionable in the offseason. But style doesn’t have to end when the sun goes away. Cooler temperatures are just an excuse to pile on more cool – and toasy woolen – pieces. Thankfully, the possibilities are as endless on Island as the nights are long.

Above: One hundred percent alpaca beanie, available in a variety of colors ($29, Island Alpaca in Oak Bluffs).

Faribault Woolen Mill Co. Dobby Stripe merino wool scarf ($60, Backwater Trading Company in Edgartown).

LF Fashion Company knit cowl ($24, Citrine in Vineyard Haven).

Heritage knitted lambswool Boyd Socks in grey Fair Isle pattern ($29, Sun Dog in Edgartown).

Fashion Expressions leather gloves with lambswool lining ($54, Citrine).