When it’s ungodly chilly out here in New England, I immediately dream of summer on the Vineyard. Blame my Northeast residence, but everything about that little island just screams quintessential prep to me – in the best way possible. So – in the name of summer daydreaming – I’ve set about planning my ensembles for my ideal summer day on the Vineyard. Care to escape with me?

9AM: The Vineyard has activities for days, and a little morning sailing sounds like the most whimsical way to start the day. And what’s sailing without some nautical stripes?

12PM: Nothing beats New England clam shack fare. High-waisted shorts (paired with a pearl necklace, of course) are the perfect casual bottoms for such a low-key experience. As a bonus, they slide on perfectly over your bathing suit.

2PM: It’s the Vineyard, so the beach is a given. A printed one-piece makes for the ideal preppy option.

4PM: When temps cool off, it’s time for some antiquing. Like any good New England town, the Vineyard has plenty. In my summery dream, I’m wearing this retro-inspired dress.

7PM: It’s been a long day, so go ahead and indulge your palette. It’s a given that stellar restaurants are everywhere in this huge tourist destination. And for the attire? This dress is dark enough for night, but breezy enough to bring in that beach mentality.

Countdown to summer… commence.

Our Head-to-Toe Preppy: From Plaid Skirts to Polos Boutique is open now.

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Going on a getaway is fun in itself, but add hue-happy colors and floral-splashed prints and there may not be enough room on the camera for all the picture-perfect moments. Equal parts preppy and nautical, this chic collection has styles for both little and grown-up fashionistas, which makes it perfect for mother-daughter photo ops (with a tropical backdrop, of course).

Our Lilly Pulitzer Boutiques open Monday, January 7, at 11AM ET.

By Brianna Lapolla, Staff Writer

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Prepsters, rejoice. Rugby Ralph Lauren is almost here, and with it, the answer to your Ivy-inspired apparel dreams. While you may already know Rugby’s look – old-school gone edgy – quite well, a rundown on the brand’s background can only intensify the love, right? (Right.)

The brand launched in 2004, as a younger, edgier take on that American-style prep its parent company, Polo Ralph Lauren, is known for.

Not sure if it’s Rugby Ralph Lauren? If the rich materials, delicious structures, and ubiquitous plaids aren’t a dead giveaway, then look for a skull and crossbones motif, or “R.L.F.C.” – two of the brand’s most recognizable logos.

Rugby Ralph Lauren’s staple product is – you guessed it – the rugby shirt. Originally, the shirts were produced in the school colors of the college towns in which Rugby stores resided.

Taylor Swift is a fan. Need we say more?

Our Rugby Ralph Lauren Women Boutique opens Wednesday, December 12, at 11AM ET.

By Sarah Stanley, Staff Writer

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