Courtesy of Michelle Greaney

Tastemaker Jackie Greaney’s unabashedly preppy Instagram account (with almost 40,000 followers) is the standard-bearer for classic New England style.

By Caroline McKenzie
Courtesy of Amy Tyson

Morning Joe

Perk up with the Maine Roast at Boulangerie. Located in a salvaged red barn, the from-scratch bakery also churns out piping-hot ham-and-cheese croissants.

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Sura Ark
Sura Ark/Getty

Dog Trot

My black Labrador, Poppy, always tags along. We stroll the quaint streets of historic Dock Square, where I reward her (almost-always) good behavior with a lobster-shaped cookie from Scalawags Pet Shop. 

Anne Cartwright

Must-Shop Boutiques

For something vintage, Camp Wool is an untapped gem, with local antiques such as old oyster tins. At Found, everything is made in Maine. My favorite finds are the old-school leather-and-canvas Liza Hennessy totes. 

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Courtesy of Chris Becker

Worth the Splurge

You’ll linger at local photographer Chris Becker’s airy studio. His series of floating lobster cars, all snapped on the surrounding waters, come framed and ready to hang on a seafaring gallery wall.

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© 2017 Alex Warman
Courtesy of Alex Warman

Dinner Date

No day is complete without dinner at The Ramp. The ramshackle joint has views of the working Cape Porpoise lobster port. You can’t go wrong with the seafood-focused menu, but I’ve found the buttery tuna melt and a dark-and-story are a nice combo. (If you want something more upscale, try the sister restaurant, Pier 77, located upstairs.) 

Courtesy of Manufacturers

Kennebunkport Uniform

I live in Binghamton Knitting Company’s rollneck sweaters; you can purchase them at Dock Square Clothiers. Other essentials: worn-in jeans, a Barbour coat, and Ilse Jacobsen rubber boots.

  • Barbour Beadnell Polar Quilted Jacket in Navy, $275; bloomingdales.com
  • Binghamton Knitting Company Ladies’ Nautical Striped Rollneck Sweater in Nautical Red and Natural, $70; docksquareclothiers.com
  • J.Crew 8" Toothpick Jean in Lyric Wash, $125; jcrew.com
  • Ilse Jacobsen Women’s Rub1 Boot in Deep Red, $199; moosejaw.com