Lookbook

The High Summer Lookbook

By Drake's

Jun 4, 2025

The High Summer Lookbook

Talk to anyone living in New York City about The Hamptons and you’re guaranteed to get a strong reaction. Raised eyebrows, an exhalation of breath, or a rhapsody about where to stay, what to eat, and who to see. They’ll ask if you’re driving there and, when you say yes, they’ll say to watch out for the traffic.

A summer haven for stressed out Manhattanites and a collective of old money elite, it’s also a beautiful corner of America, pristine coastline jutting out onto the Atlantic, rolling sand dunes and white-washed houses, and little red cardinals darting through the woods.

Alongside our friend Geoff Haggray, a photographer, occasional model and all-round stylish guy, we crawled through city traffic and onto the highway. Up to Greenport, a ferry to Shelter Island, sunshine gently flickering through the trees in the early days of summer. The real crowds will start to descend after Memorial Day. We’re just missing them. We push on to Sag Harbor, a neat hamlet that used to be a base for whalers—sailors who would spend months, and sometimes even years, away from home navigating stormy seas.

Highlights from our summer collection include surf cagoules in Madras cotton, overcheck linen Games blazers, warm weather shirts in gingham, seersucker and cuban collar linen, along with handmade Turkish shoes by our friends at Sabah, Kelim print drawstring shorts, new caps and bags by Maison Bengal.