Ah, Sag Harbor. One of those most charming parts of the Hamptons that is far less crowded than her neighboring sister towns. There’s a wholesomeness to this beach front village that has a classic picturesque vibe to attracting so many. Speckled with quaint ice cream shoppes, Riva yachts and now the Classic Six store front - its  blooming, vibrant atmosphere transitions seamlessly from day to night. Out of towners are welcomed - so enjoy this guide to experiencing the best of Sag Harbor while wearing your best. 

During the Day

Start your day with a leisurely stroll along Main Street and explore the bespoke shops (ehhhemmm Classic Six), art galleries, and boutiques that line the street. Stop by coffee shops like SagTown Coffee or Grindstone Coffee & Donuts for a morning pick-me-up. Head to the beach after breakfast and spend a lazy afternoon by the water, soaking up the sun and taking a refreshing dip. For lunch, make your way to one of the waterfront restaurants like The Dock House or Dopo La Spiaggia for an indulgent and delicious lunch with picturesque views of the harbor.  Before you head back to get ready for dinner, we recommend heading up to the top of Main street to visit us right at the corner of Main and Madison! (next to Relax and across from Love Shack Fancy!) 

Look: Denim cut offs and Donna blouse, farmers market bag and choice of straw hat or vintage baseball cap. 

During the Evening:

Embark on a sunset cruise to experience the beauty of Sag Harbor's waterfront during golden hour. Definitely a memorable experience. Once the sun goes down head to one of the favorite local eatery’s that cook with season ingredients like Lulu Kitchen & Beacon Sag Harbor. Make your reservations at the elegant American Hotel ahead of time and have yourself a little slice of Hampton history to go along with it. Sag Harbor has several bars and lounges where you can unwind with a drink. Visit establishments like Paige at 63 Main, Murf's Backstreet Tavern, or Tutto Il Giorno for a relaxing evening in a cozy atmosphere.

Look: Twiggy with a silk ascot, oversized sunglasses (for that low sun set)  strappy sandals and a crossbody