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Old Money Style Beach Outfit Ideas for a Wealthy Nautical Look

As seasoned stylists with over three decades of experience outfitting dashing gents from coast to coast, we’ve charted a course through the tranquil waters of nautical elegance and dropped anchor at the shores of timeless sophistication.

So, batten down the hatches and prepare to set sail on a journey that will elevate your Old Money beach fashion style to the upper echelons of coastal class.

Last month, we styled Theodore, a 26-year-old shipping magnate and avid yachtsman.

Hailing from a long line of New England seafarers, Theodore was well-acquainted with the traditions of nautical style but was adrift in a sea of uncertainty when striking the perfect balance between old money refinement and laid-back beach charm.

“I want to embody the essence of the Kennedys at Hyannis Port but don’t want to look like I’m trying too hard.”

Together, we navigated the sartorial seas and dropped anchor on five stunning ensembles that perfectly captured the relaxed spirit of Old Money at the beach.

Theodore’s new look was nothing short of remarkable; he clinched a transatlantic shipping deal and garnered praise from the most discerning members of the yachting elite for his impeccable taste.

Now, let’s trim the sails and embark on a voyage through the five essential old-money beach outfits that will have you looking like you just stepped off the pages of a vintage issue of Town & Country.

1. The Croquet Club Championship

For a day of friendly competition on the manicured lawns of your local croquet club, opt for a crisp white cotton polo shirt from Sunspel.

It features the brand’s signature mother-of-pearl buttons and a contrasting navy-tipped collar.

Pair this with tailored navy linen trousers from Incotex, celebrated for their unparalleled fit and exquisite Italian craftsmanship.

Complete the look with a pair of brown leather penny loafers from J.M. Weston, a brand synonymous with timeless elegance, and a woven leather belt in a rich chestnut hue from Brunello Cucinelli.

For a touch of old-world sophistication, accessorize with a pair of tortoiseshell clubmaster sunglasses from Oliver Peoples and a vintage stainless steel tank watch from Cartier, like the iconic Tank Louis Cartier.

2. The Oyster Bay Brunch

When attending a leisurely brunch at a refined waterfront establishment, such as the Oyster Bar at the Sagamore Yacht Club, combine the breezy elegance of linen with the nautical charm of Breton stripes.

Start with a classic Saint James Meridien II Breton shirt in a traditional ivory and navy colorway, revered for its superior cotton jersey fabric and impeccable construction.

Layer this under a lightweight, unstructured linen blazer in a soft sand hue from Boglioli, a brand renowned for its relaxed Italian tailoring.

Pair these with pleated linen trousers in a complementary ecru shade from Rubinacci; a Neapolitan tailoring house celebrated for its exquisite attention to detail.

Finish the ensemble with a pair of hand-stitched brown suede loafers from Crockett & Jones, a British shoemaker that has been crafting exceptional footwear since 1879, and a braided leather belt in a rich caramel tone from Ettinger, a royal warrant holder known for its superlative leather goods.

3. The Sundown Sail

As the sun dips below the horizon and you set sail on a private yacht for an evening of coastal revelry, embrace the maritime spirit with an outfit that seamlessly blends old-money sophistication with a touch of nautical whimsy.

Begin with a crisp white linen shirt from Charvet, a Parisian institution renowned for its luxurious fabrics and impeccable craftsmanship.

Pair this with tailored navy cotton twill trousers from Hereditary Trousers, a byword for superior fit and comfort.

Layer on a cream-colored cable-knit cotton sweater from Ralph Lauren Purple Label, an iconic American brand that epitomizes the essence of old money style.

Complete the look with a pair of navy and white nubuck boat shoes from Quoddy, handcrafted in Maine using time-honored techniques, and a braided leather bracelet with a polished silver anchor clasp from Miansai, adding a touch of seafaring charm to your ensemble.

4. The Regatta Royale

When attending a prestigious sailing regatta, such as the Newport Bucket or the Nantucket Race Week, opt for an outfit that pays homage to the rich traditions of competitive yachting.

Start with a navy blue performance polo shirt from Musto, a brand at the forefront of sailing apparel for over 50 years, featuring the event’s embroidered logo on the chest.

Tuck this into a pair of white cotton twill Bermuda shorts from Orlebar Brown, a British brand celebrated for its tailored approach to swimwear.

Complete the look with hand-sewn brown leather deck shoes from Dubarry, an Irish brand with a storied heritage in nautical footwear, and a woven leather belt in a rich tan hue from Ettinger.

Accessorize with a pair of polarized aviator sunglasses from Randolph Engineering, a brand favored by the U.S. military for its exceptional clarity and durability, and a stainless steel diving watch with a navy blue NATO strap from Tudor, like the iconic Black Bay Fifty-Eight, for a touch of vintage-inspired seafaring style.

5. The Clambake Chic

For a festive beachside clambake under a billowing white tent, embrace the vibrant colors and playful patterns that define the essence of summer style.

Begin with a light blue and white gingham check linen shirt from Gitman Vintage, a brand celebrated for its authentic American heritage and exceptional craftsmanship.

Pair this with a set of Nantucket red cotton twill trousers from Murray’s Toggery Shop, a true icon of New England style.

Layer on a cream-colored shawl-collar cardigan in a lightweight linen and silk blend from Brunello Cucinelli, adding a touch of refined insouciance to your ensemble.

Finish the look with a pair of brown leather fisherman sandals from Yuketen, handcrafted in Mexico using traditional techniques, and a braided cotton belt in a complementary ecru shade from Anderson’s, an Italian brand synonymous with exceptional quality and attention to detail.

Accessorize with tortoiseshell wayfarer sunglasses from Moscot, a New York City institution renowned for its timeless eyewear designs, and a woven leather and silver anchor bracelet from Paul Hewitt, adding a touch of nautical charm to your look.

Dos and Don’ts

To ensure you navigate the sartorial seas with ease and confidence, keep these essential style buoys in mind:

Do’s Don’ts
  • Opt for a color palette that evokes the hues of the sea, sand, and sky
  • Choose timeless, well-tailored silhouettes that flatter your physique
  • Accessorize with purpose, selecting pieces that add a touch of nautical charm to your ensemble
  • Invest in high-quality, natural fabrics like linen, cotton, and lightweight wool blends
  • Pay meticulous attention to grooming and the finer details of your outfit
  • Avoid trendy, fast-fashion garments that lack quality and longevity
  • Steer clear of overly bright, neon colors that clash with the understated elegance of old-money style
  • Don’t underestimate the importance of fit – ill-fitting clothes can sink even the most carefully curated outfit
  • Refrain from overdoing it with flashy logos or overtly branded items
  • Don’t let the condition of your footwear and accessories fall by the wayside – scuffed shoes or frayed belts can mar an otherwise impeccable look

In the end, mastering the art of old money beach style is all about striking the perfect balance between timeless elegance and laid-back coastal charm.

By incorporating these five essential outfit formulas and heeding the sartorial guidance of the do’s and don’ts, you’ll embody the spirit of a modern-day maritime aristocrat, turning heads and leaving an indelible impression wherever your seafaring adventures may take you.

Chart Your Sartorial Course with The VOU

Gentlemen, navigating the complex currents of old money beach style can seem daunting, especially if you don’t have a trust fund or a sprawling seaside estate to your name.

The VOU is your trusted style lighthouse, guiding you through the treacherous waters of sartorial uncertainty and illuminating the path to unparalleled coastal elegance.

Imagine yourself strolling along a pristine stretch of white sand, the salt-kissed breeze tousling your hair as you confidently sport an ensemble that seamlessly blends nautical heritage with contemporary sophistication.

Picture yourself at the helm of a sleek yacht, engaging in lively discourse with the crème de la crème of the sailing world, secure that your impeccable style sets you apart from the crowd.

This is the transformative power of old-money beach fashion, and it’s well within your grasp.

Our seasoned style navigators at The VOU will work with you to curate a bespoke beach wardrobe that reflects your unique personality and aspirations.

We’ll help you navigate the vast ocean of sartorial possibilities, ensuring that every garment and accessory you select is a testament to your discerning taste and unwavering commitment to excellence.

When you enlist our services, you’re not merely updating your closet – you’re embarking on a journey of self-discovery and personal growth, armed with the confidence that comes from knowing you look your absolute best.

So, dear friends, why waste another moment adrift in a sea of sartorial mediocrity?

Drop anchor at The VOU today, and allow us to be your guiding star on the path to old-money beach-style mastery.

Book your complimentary consultation now and prepare to set sail on the most thrilling and rewarding fashion voyage of your life.

Until we meet again, gentlemen, may your sails be full, your compass true, and your style impeccable.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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