October 25, 2025

The chill in the air means its time to leave the coast behind and escape to your wooded winter oasis

Good morning, and welcome to this weeks edition of The Weekly Preppy! Now that fall is in full swing, our minds have left the ocean and are creeping closer to the ski slopes. We’ll scratch that itch slightly this week by looking at some dream ski homes for any prep enthusiast. There’s a lot to cover this week including:

The Weekly Preppy’s top finds & deals for preppy clothing and accessories this week

As the days get shorter (and colder), our minds drift away from the coast and towards the mountains. Instead of dreaming of walks on the beach and afternoon sails, it’s hunting trips and ski weekends that we obsess over. If you’ve been picturing your ideal winter escape, we may have found it for you in Newry, ME.

Right around the corner from the Sunday River resort, which ranks as a top 10 east coast ski resort by SKI mag, and close to Grafton Notch State Park, Newry makes a spectacular winter hideaway. If you’re ready to make the move, we’ve curated a list of excellent winter homes in the area, so read on to select your dream house!

With massive windows and living room views of Sunday River Resort and Mahoosuc Range, it would be hard to turn down this dream home. 5 bedrooms and 3.5 total baths make it big enough to host friends and family as well! Picture yourself eating a delicious breakfast in that dining room before heading out to the slopes this winter, or curling up on the couch to read a good book while snow falls down.

If you are more of a log-cabin purist, this home might be the one for you. The flooring, ceiling, and walls are entirely cabin style hardwood on the interior, and a beautiful stone fireplace centers the living room which also provides breathtaking views of the wilderness landscape. It may look remote, but it’s also only a 6-minute drive to the base of Sunday River resort, so you can be skiing pretty soon after you wake up. Just imagine sipping a warm cup of coffee at 7am while you watch snowfall over those trees and hear the fireplace roar.

For those seeking a slightly more modern retreat, you may be interested in 40 Appalachian. As its description says, the design suits both comfort and functionality. The inside is beautiful, with a brand new kitchen, and sensible nods to the remote location, you’ll know you’re in the mountains but won’t feel as much like you’re camping. There’s cozyness around every corner in this house, so it will be easy to find a place to get comfortable and read The Weekly Preppy each week in the winter.

Newry, ME is a picturesque preppy winter getaway, but it isn’t the only one. We’re curious, what’s your dream (or real) winter home location? Reply to this email to let us know you’re wintering, or where you hope to be wintering someday soon!

This week, The Weekly Preppy released their official power rankings for prep brands in 2025. We’ll give you a sneak peak of the top 5 here, make sure to read the full article to see all 100 (yes, 100) brands ranked. Maybe you’ll even learn some new ones to add to your closet!

Read the Article: Preppy Brand Power Rankings

It would be difficult to place the inventor of the polo shirt outside the top ten on this list. French tennis champion René Lacoste revolutionized sportswear in 1933 with his creation. The short-sleeved, soft cotton piqué shirt with a ribbed collar was a more comfortable alternative to the woven long-sleeve shirts worn on tennis courts. The iconic crocodile logo (a nickname earned for Lacoste's tenacity on court) made it one of the first designer logos, and American preppies immediately embraced it as leisurewear perfection. The polo shirt in white, navy, or pastel colors became as essential to the preppy uniform as khakis and loafers. Lacoste represents the athletic side of the prep lifestyle; tennis, golf, and country clubs.

Leon Leonwood Bean founded his mail-order company in Freeport, Maine in 1912, creating the iconic Maine Hunting Shoe (Bean Boot) when he combined leather uppers with rubber bottoms for his own hunting expedition. That commitment to functional, honest products for outdoor pursuits became the foundation of a brand that epitomizes New England practicality and durability. The Bean Boot remains virtually unchanged and completely iconic. It’s a preppy status symbol that's actually earned through genuine utility. Beyond the boots, LL Bean's canvas totes, Norwegian sweaters, and chamois shirts became campus staples, representing a democratic prep that valued quality and function over pretension. The brand embodies the Maine character: unpretentious, hardworking, and built to last generations.

Ralph Lauren didn't just participate in preppy culture, he represented it. Starting with wide Polo ties in 1967, Lauren built an empire by romanticizing the American upper class, from the Hamptons to the hunting lodge, making preppy style accessible to anyone who could afford it. His genius was understanding that prep wasn't just clothing but a complete lifestyle, a mythology of old money, country clubs, and effortless elegance. Through Purple Label, Polo, and RRL, he created products at every price point while maintaining the dream. Ralph Lauren made "preppy" a global language.

Founded by Jacobi Press in 1902, J. Press became the official outfitter of the Ivy League, with shops near Yale, Harvard, and Princeton that served as the arbiter of collegiate style for generations. The brand's natural shoulder sack suits, three-roll-two blazers, and repp ties defined what "Ivy" meant during its golden era from the 1950s through the 1970s. J. Press never chased trends or compromised their traditional silhouettes, earning them reverence among purists who view them as the keeper of the flame. While smaller today, the brand maintains its commitment to American manufacturing and traditional construction. For those who know, J. Press represents prep in its purest, most authentic form, the real deal that inspired all the imitators.

Founded in 1818 in New York City, Brooks Brothers is the oldest continuously operating clothing retailer in America and the absolute bedrock of American preppy style. The brand invented the button-down collar shirt in 1896, introduced the seersucker suit to America, and created the iconic #1 repp stripe tie. For over two centuries, Brooks Brothers dressed everyone from Abraham Lincoln to JFK, establishing the visual language of American business and casual elegance. While the brand has faced ownership changes and quality inconsistencies in recent years, its historical significance as the foundation of prep remains unassailable. This is where it all began.

A true preppy is characterized by intellectual honesty, always seeking to find and spread truth. In any and all situations, our priority must be identifying what is true and building from there. In his speech at Harvard, JKF embodied mindset and this week should all seek to apply it to our daily lives.

Don’t look now, but before long we’ll be dropping The Official Preppy Calendar for 2026! Stay on top of every important date in the preppy world ranging from The Newport Folk Festival to the Harvard-Yale game. Can’t wait to get yours? Join the waitlist today to make sure you get one while supplies last.

Thanks for joining us for this weeks edition of The Weekly Preppy!
Until next time,