In this article, 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 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 is well-acquainted with nautical fashion but was adrift in a sea of uncertainty on how to achieve modern old money 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 Old Money beach style.
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. Croquet Club Look
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 with the brand’s signature mother-of-pearl buttons and a contrasting navy-tipped collar, creating a classy Country Club aesthetic.
Pair with tailored navy linen trousers from Polo Ralph, a pair of brown leather penny loafers from J.M. Weston – an old money brand synonymous with timeless elegance – and a woven chestnut leather belt from Brunello Cucinelli.
Accessorise 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. Oyster Bay Brunch Look
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 colourway, 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 designer heritage 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. Sundown Sail Look
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-chic brand renowned for luxurious fabrics and impeccable BCBG style.
Pair this with tailored navy cotton twill trousers from Hereditary Trousers, a byword for superior fit and comfort.
Layer on a cream-coloured cable-knit cotton sweater from Ralph Lauren Purple Label, an iconic American brand that epitomises 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-honoured techniques, and a braided leather bracelet with a polished silver anchor clasp from Miansai, adding a touch of seafaring charm to your ensemble.
4. Regatta Royale Look
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.
Accessorise with a pair of polarised aviator sunglasses from Randolph Engineering, a brand favoured 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. Clambake Chic Outfit
For a festive beachside clambake under a billowing white tent, embrace the vibrant colours and playful patterns that define the essence of summer preppy style.
Begin with a light blue and white gingham check linen shirt from Gitman Vintage, a brand celebrated for its authentic American preppy heritage and craftsmanship.
Pair with Nantucket red cotton twill trousers from Murray’s Toggery Shop, a true icon of New England preppy style.
Layer on a cream-coloured 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 old-money brand.
Accessorise 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.
Men’s Beach Attire Do’s and Don’ts
To ensure you navigate the sartorial seas with ease and confidence, keep these essential style buoys in mind:
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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.
Style with The VOU
Knowing the look of nautical preppy fashion and purchasing expensive beach brands is one thing.
But knowing how to match them according to your seasonal colour and body shape…well, that’s a different thing.
True fashion mastery lies in knowing and matching your body shape/type with your seasonal colour – skin, eye, and hair colours.
It requires understanding how to shop and pair the most ideal garments, footwear, and accessories from the most relevant, heritage brands.
This is paramount to being able to dress correctly by body shape, occasion, location, time of the day, and lifestyle.
Find Your Body Shape
Different garments flatter different physiques so discover your body shape now by taking our free body shape quiz for men.
Identify Your Best Colors
Fashion comes in a wide range of colours, but not every hue will complement your natural colouring so find out your ideal colours with our free seasonal colour quiz for men.
Then, learn how to dress by occasion, location, season, and even time of the day.
Dress for the Occasion
Understanding how to choose and style garments from relevant heritage brands, and style them by occasion, season, location, and body shape is crucial.
From casual weekends to formal events, each occasion requires a unique approach to styling.
To save time, headaches, and even money, get in touch with The VOU’s expert stylists now.
Get Expert Styling Advice
Take our comprehensive fashion style analysis for men, and let our expert stylists guide you in selecting and curating items of maximum impact in a wardrobe that communicates success and confidence.
Remember, owning luxury brands isn’t enough. To look stylish, confident, wealthy, and successful you must match your body shape, colour palette, season, occasion, location, time of the day, to perfection.
With these tools and expert guidance, you’ll not just wear the brand—you’ll master it, creating a wardrobe that truly reflects a unique fashion taste and many achievements.