Old Money Summer: What the Elite Wear on Vacation

When summer arrives, Old Money gentlemen don’t abandon elegance for flip-flops and flashy logos. Instead, they retreat to coastal estates, countryside villas, or historic resorts with a wardrobe rooted in timelessness, quality, and understatement. From Portofino to The Hamptons, their style whispers legacy and ease.

This is your definitive guide to dressing like a true Old Money man on vacation—refined, relaxed, and effortlessly elite.

1. Linen Done Right: The Vacation Fabric of Old Money

No fabric says summer sophistication like linen. Breathable and timeless, linen garments are staples in Old Money wardrobes.

Key Pieces:

  • Linen Button-Down Shirts:Old Money Style Men In crisp white, sky blue, or muted stripe. Worn slightly loose, sleeves often rolled.

  • Linen Trousers: Tailored but relaxed. Always hemmed, never dragging.

  • Linen Suits: For summer weddings or dinners at private clubs—pair with suede loafers or leather espadrilles.

Tip: Embrace the wrinkles. Perfectly pressed linen looks forced; natural creases signal authenticity.

2. Polo Shirts with Pedigree

The Old Money polo is not the overly tight, brand-plastered version seen on social media. Instead, it’s a well-made, often faded staple from a heritage label.

Ideal Characteristics:

  • Muted tones: Cream, dusty navy, moss green

  • Soft collars: No stiff, plasticky materials

  • Subtle branding: Preferably none

Tucked into tailored shorts or worn under lightweight sweaters, the polo is your go-to for golf clubs, yacht decks, or countryside strolls.

3. Swimwear That Doesn’t Shout

Forget board shorts and flashy patterns. Old Money swimwear is tailored, subtle, and often monochromatic.

Look For:

  • Mid-thigh cut: Refined and flattering

  • Neutral tones or classic stripes

  • Elastic waist with drawstring—not logo-heavy brands

Top choices include Orlebar Brown, Vilebrequin (in solid colors), or classic Ralph Lauren swim trunks. After the beach, throw on a linen shirt or cotton popover and you’re instantly resort-ready.

4. Footwear: From Yacht to Café in Style

Summer footwear for Old Money men is about comfort and quiet refinement.

Summer Essentials:

  • Espadrilles: In suede or canvas, in colors like navy, cream, or tobacco

  • Leather Loafers: Soft, broken-in, and never overly polished

  • Boat Shoes: Worn naturally, not styled for Instagram

  • Driving Shoes: Perfect for countryside drives and lazy afternoons

Sandals? Only leather slides. Never rubber flip-flops—not even poolside.

5. The Power of Accessories—Worn Lightly

Old Money accessories serve a function but never steal the show.

Must-Haves:

  • Panama Hat or Straw Fedora: Protects from the sun and elevates any look

  • Woven Leather Belt: Classic, understated

  • Tortoiseshell Sunglasses: Preferably Persol or vintage Ray-Ban Clubmasters

  • Canvas or Leather Weekender Bag: Monogrammed? Only on the inside.

Jewelry is minimal—perhaps a family heirloom watch or signet ring. No gaudy chains or oversized logos.

6. Outerwear for Breezy Evenings

Cool summer nights on the coast call for lightweight layers with pedigree.

Timeless Summer Jackets:

  • Cotton Harrington Jacket in navy or khaki

  • Unstructured Linen Blazer for formal dinners or museum visits

  • Cable Knit Sweater or Cardigan casually thrown over shoulders (not tied, just draped)

Remember: style is not about trying hard. It’s about appearing naturally elevated—even when the wind picks up.

7. The Old Money Vacation Color Palette

You’ll never see an Old Money gentleman in neon or shouty prints. The vacation wardrobe stays within a muted, timeless palette:

  • Ivory, Sand, Stone

  • Navy, Olive, Sky Blue

  • Dusty Pink or Muted Coral (sparingly)

  • Earthy Browns and Grays

This restrained palette reflects stability, longevity, and effortless blending with the surroundings—whether it’s a Tuscan vineyard or a coastal marina.

8. Grooming & Posture: The Finishing Touches

Old Money elegance on vacation extends beyond fabric. It’s in the way a man carries himself, even when barefoot on a yacht deck.

  • Hair trimmed and styled naturally

  • Skin protected by discreet SPF, not tinted lotions

  • Posture straight, gestures subtle

  • Never loud, always present

Simplicity isn’t laziness—it’s intentional excellence. That’s the Old Money code.

Conclusion: Dress Like You Belong

Vacationing in Old Money style isn’t about playing dress-up—it’s about channeling a heritage of discernment and restraint. You won’t find these men chasing trends, because they were raised in environments where what you wear should reflect who you are—not what you’re trying to prove.

So whether you’re heading to Capri, Montauk, or Provence, pack with intention. Linen, loafers, and legacy are all you need.

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