The Inspiration
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The Inspiration

Reese Witherspoon's classic beach look was made for sitting beachside along the Maine coast. It's cute but not flashy — right on point for casual days seaside.

Source: FameFlynet
The Look
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The Look

Mimic Reese's quintessential beach style with a sweet printed suit, comfy espadrilles (for roaming the rocky coast), and — of course — an L.L. Bean tote.

What to pack:

The Inspiration
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The Inspiration

Rain or shine, Jordana Brewster stays on trend — with just a hint of a preppy twist. Her simple American-girl style is perfect for stealing for a day out in "Vacationland."

The Look
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The Look

Truthfully, you don't need much for a day of sightseeing in Portland. In fact, you'll want to keep it simple — to go from beach to pier for a sit-down dinner. Layer up a go-with-everything striped tank dress with a denim jacket for the night chill, then tote a bag that's big enough to hold a swimsuit. Walkable sandals are always a plus — and get in on the local flavor with a cheeky iPhone case.

What to pack:

The Inspiration
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The Inspiration

Amber Heard's breezy Summer style is the kind you'll live in on your trip. She makes it effortless with just one great dress and a few low-key accessories that feel perfectly seasonal and totally unfussy.

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The Look
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The Look

You'll be happy you have this chic little sundress in your arsenal. It'll keep you cool, not to mention it goes day to night with the simple change of accessories. We'd start simple with flat sandals and a cool bag you can take to the beach.

What to pack:

The Inspiration
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The Inspiration

Cool-girl Kate Bosworth might not scream New England style icon, but she knows how to balance the classics with the trends, making her a perfect fashion star to steal a little inspiration from. She takes great staple pieces like this shirtdress and styles it with eye-catching accents to elevate the look. Note: you'll want to do the same with the stuff in your suitcase.

Source: FameFlynet
The Look
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The Look

A staple shirtdress is a polished piece you can style up with Summer flair, specifically a touch of patriotic red, nautical accessories, and a great pair of espadrilles. You won't need much more than this to get dressed up for a night out in Portland.

What to pack:

The Inspiration
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The Inspiration

She may be a Brit, but Pippa Middleton's style has "New England gal" written all over it. With a classic color combo, easy proportions, and a few ultrasummery accents, she nails the Maine dress code with sophistication.

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The Look
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The Look

For a riff on Pippa's preppy take, we'd swap in white jeans to pair with a flowy beat-the-heat button-down, then finish with shades and a few dressed-up add-ons, like a metallic pair of Jack Rogers for dinner out in Old Port.

What to pack:

While You're There . . .
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While You're There . . .

Do yourself a favor and drive up Route 1 along the gorgeous Maine coastline. You'll know then why the state's earned its reputation as "Vacationland."

Stop along the way if you like, but whatever you do, don't pass up the opportunity to stop off in Bar Harbor for the breathtaking views at Acadia National Park. If you're feeling adventurous, set out to hike Cadillac Mountain. If not, take in the landscape with a table at Jordan Pond House, where lunch comes with a view — and a popover!

While You're There . . .
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While You're There . . .

You'll need to do two things upon your arrival: get yourself an authentic Maine lobster roll, stat, and get yourself to Freeport — not just to check out the L.L. Bean flagship store (open 24 hours a day, 365 days a year) and take your photo with a giant Bean boot — but for some serious outlet power shopping. Freeport is stocked with outlets like Coach, Burberry, and J.Crew, so get your power-shop on by day, then head to the Old Port for a sunset view and dinner by the water.