November 1, 2025

October is complete, which means less than 2 months until 2026! Are you ready for the new year?

Good morning, and welcome to this week’s edition of The Weekly Preppy! October is over, so we are officially two months deep into the ‘ber months. Let’s make sure to use these last two well. We have an action-packed edition for you today to help get you ready for the upcoming year, and provide you your weekly does of preppy tailored reading. On the docket for today:

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

Tradition is an undeniably important element of the preppy lifestyle. We orient our lives around recurring events that ooze heritage, community and nostalgia. While this will look different for all of us, there are certain dates that are crucial to the prep lifestyle no matter what. Lets dive into these dates, and learn why they should be in every preppy’s calendar.

Date in 2026: October 16–18

The Head of the Charles Regatta, held every October on Boston’s Charles River, is the largest two-day rowing event in the world and one of the crown jewels of New England tradition. Founded in 1965 by members of the Cambridge Boat Club, the race was designed as a “head race” (a time trial format inspired by English rowing customs). The event attracts elite rowers, Ivy League crews, and a devoted social crowd, partly because it takes place at the height of autumn, when the riverbanks are covered with fall foliage. For the preppy community, the event represents much more than sport. It’s a celebration of heritage, camaraderie, and the collegiate spirit that defines classic East Coast style. Blazers, Barbours, and boat shoes are as much a part of the weekend as the racing itself.

Date in 2026: November 21

Collegiate energy is a quintessential element of the preppy lifestyle, and few dates in the calendar represent that better than The Harvard–Yale Game. First played in 1875, it stands as a pillar of Ivy League tradition. Held each November, alternating between Harvard Stadium in Cambridge and the Yale Bowl in New Haven, the matchup draws students, alumni, and families for a weekend steeped in school spirit and nostalgia. For preppy circles, this is a social ritual that blends old-school rivalries with timeless style. Tailgates overflow with tweed coats, camel hair scarves, and hot toddies, capturing the essence of New England prep culture at its finest.

Date in 2026: May 2

This next date takes a step away from New England and moves south, to Kentucky. The Kentucky Derby, first run in 1875 at Churchill Downs in Louisville, is the longest continuously held sporting event in the United States and a pinnacle of Southern tradition. Taking place each May, it marks the height of the spring social season and the first leg of horse racing’s Triple Crown. Beyond the race itself, the Derby is a celebration of elegance and pageantry. Seersucker suits, linen dresses, and bold hats are as iconic as the mint juleps in hand. For preppy enthusiasts, it represents the perfect blend of sport, society, and spectacle, where iconic style and gentle Southern charm come together for one unforgettable weekend.

Date in 2026: June 29-July 12

Crossing the Atlantic, we are met with another iconic sporting event in the preppy calendar. The Wimbledon Championships, first held in 1877, is the oldest and most prestigious tennis tournament in the world. Played each summer at the All England Club in London, Wimbledon is steeped in tradition with grass courts, an all-white dress code and strawberries and cream served to spectators. It embodies the grace, discipline, and understated elegance that align perfectly with preppy sensibilities. For the preppy crowd, Wimbledon represents the height of classic sport and refinement, where athleticism meets etiquette.

Date in 2026: Nov 26

For preppy families, Thanksgiving is the cherished gateway to the holiday season; a time when generations gather at home to reconnect and reflect. The day blends warmth and tradition: roaring fireplaces, heirloom silver, tartan tablecloths, and well-worn family recipes passed down through the years. More than just a feast, Thanksgiving embodies the preppy values of family, gratitude, and continuity, marking the start of a festive stretch filled with reunions, winter sports, and seasonal celebrations. It’s a moment to slow down, return to one’s roots, and savor the rituals that make old traditions feel timeless.

Honorable Mentions: The Big E, The Masters, The First Day of Fall

Want to make sure you have all of these dates (and more!) pre-marked in your calendar, along with classic preppy imagery for each month? Join the waitlist for The Official Preppy Calendar now!

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.

In the preppy world, accessories aren't afterthoughts. They're the punctuation marks that complete the sentence. While a navy blazer and khakis might form the foundation, it's the carefully chosen watch, the well-worn belt, or the classic eyewear that tell your story. These pieces signal membership in a tradition that values heritage, quality, and that ineffable sense of belonging to something bigger than trends. They're the quiet markers of a lifestyle built on weekend sailing trips, family compounds, and the kind of seemingly effortless good taste that never needs to announce itself.

1. The Needlepoint Belt

Nothing says "I summer in New England" quite like a needlepoint belt threaded through khakis or Nantucket Reds. Hand-stitched with whimsical motifs (lobsters, golf clubs, martini glasses, or even your alma mater's mascot), these belts are both practical and deeply personal. They're conversation starters that double as family heirlooms, often gifted for graduations or milestone birthdays. The beauty lies in their imperfection; the slight variations in stitching remind you that someone's hands crafted this just for you.

Where to shop: Smathers & Branson is the gold standard here, though many treasured belts come from small needlepoint shops in coastal towns.

2. Tortoiseshell Sunglasses

The wayfarer or classic aviator in tortoiseshell acetate is practically a preppy uniform requirement. These aren't the sunglasses you nervously guard at the beach. They're the ones that have survived countless afternoons on the boat, tennis matches, and clambakes. The warm, mottled pattern works with everything from seersucker to cashmere, and they project an air of casual confidence that screams "I've been doing this since prep school." Unlike trendy frames, tortoiseshell never dates itself, making them a true investment piece.

Where to shop: Ray-Ban Wayfarers in tortoise are the classic choice, while Ben Silver is another excellent option if you’d prefer a more unique frame shape.

3. The Leather Watch

A preppy wrist isn't complete without the right timepiece, but it's less about flashy complications and more about understated elegance. Think slim cases, clean dials, and simplistic designs. The watch should be nice enough for the yacht club but durable enough for an impromptu game of touch football. It's about knowing the time, yes, but also knowing your place in a continuum of people who value punctuality, tradition, and showing up when you say you will.

Where to shop: Timex has collaborations with brands like J.Crew and Brooks Brothers which remain preppy staples. Shinola is another great starter option, while those with deeper pockets gravitate toward Cartier or Rolex watches.

4. Rope or Woven Bracelets

That slightly salt-stained rope bracelet isn't just jewelry, it's a souvenir from a life well-lived. Whether it's a braided leather band, a Turk's head knot, or a simple nautical rope in navy and white, these bracelets signal time well spent on the water. They're often layered, acquired one summer at a time from different marinas and coastal shops, each telling its own story. The best ones show their age: frayed ends, faded colors, and that permanent dampness that comes from never quite drying out between swims. They're the preppy equivalent of a surfer's shell necklace: authentic, unpretentious, and earned.

Where to shop: Kiel James Patrick built an empire on these, offering everything from simple ropes to more elaborate nautical designs. You are also certain to find them at coastal shops up and down the east coast, but let’s avoid those tourist traps.

5. The Silk Tie (or Bow Tie)

Even in our casual age, the preppy aesthetic still reveres a proper tie. Repp stripes, whimsical prints featuring ducks or sailboats, or subdued paisleys in rich colors. These are the ties that appear at Sunday chapel, holiday dinners, and any occasion requiring "smart casual." The bow tie, particularly in madras or seersucker during warmer months, adds a touch of personality without trying too hard. A well-curated tie collection speaks to occasions honored, traditions maintained, and the understanding that some moments simply call for looking properly put together.

Where to shop: Brooks Brothers for classic repp stripes, Vineyard Vines for playful prints, and Drake's of London for those seeking something more refined.

6. Pearl Studs or Strand

Pearls occupy a unique space in preppy culture, equally at home with a cable knit sweater as they are with a cocktail dress. For many, the classic pearl strand was a sweet-sixteen or college graduation gift, making them loaded with sentimental value. They represent a kind of quiet elegance that doesn't compete for attention but instead provides a polished finishing touch to nearly any outfit. Simple studs work for daily wear, while a single strand in creamy white or subtle champagne adds instant sophistication. In the preppy world, they're not costume jewelry, they're future heirlooms. 

Where to shop: Mikimoto for investment pieces, or Brooks Brothers for more accessible options that still maintain quality.

The grosgrain ribbon headband | Canvas tote bags (bearing alma mater or yacht club logos) | Signet rings | The well-worn baseball cap | Monogrammed leather keychains | Cashmere scarves in collegiate colors.

Nothing quite embodies what preppy style is about better than this quote. Our fashion is about more than the clothes we wear. Its about the lives we aspire to live and the communities we strive to develop. At The Weekly Preppy, that is exactly what we are doing! As you chose your outfits this week, remember that wearing certain clothes won’t make you preppy. Make choices in your everyday life to better represent the preppy lifestyle.

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