The Old Money Essentials for Men

In a world enamored with flash and logos, the old money aesthetic whispers where others shout. It's the cultivated elegance of generations who never had to prove anything—because their legacy already did. For the discerning gentleman, this timeless style isn’t about trends; it’s about heritage, restraint, and refinement.

Whether you’re building your wardrobe from scratch or elevating what you already own, here’s your essential guide to dressing like old money: classic, understated, and impossibly elegant.

🧥 Tailored Foundations

1. Navy Blazer (Single or Double-Breasted)
The cornerstone of any gentleman’s wardrobe. Worn with khakis or flannels, the navy blazer transitions from country club to dinner party effortlessly.

2. Grey Flannel Trousers
A go-to for cooler months. They offer quiet luxury and pair beautifully with knits or crisp shirts.

3. Cashmere Sweaters (in Earth Tones)
Think oatmeal, navy, forest green. Worn over a shirt and tie or thrown around the shoulders in spring. V-neck and crewneck are both staples.

👞 Footwear that Ages Gracefully

4. Brown Leather Loafers or Oxfords
Preferably Goodyear-welted. Brands like Edward Green, Crockett & Jones, and John Lobb are often found on the feet of men who never need to introduce themselves.

5. Suede Chukka Boots
Refined but relaxed. Ideal for weekends in the countryside or casual dinners at the club.

👔 Shirts, Ties & Subtle Sophistication

6. Oxford Cloth Button-Down Shirts (OCBDs)
White and light blue are essentials. Always well-ironed, often monogrammed in the most discreet way possible.

7. Repp Ties and Knit Ties
Classic patterns—stripes, foulards, or solids. Nothing shiny, nothing wide. The tie shouldn’t shout.

⌚ Accessories That Tell a Story

8. Vintage Watch (Not a Trophy Piece)
A slim Patek Philippe or a vintage Rolex Datejust. The goal isn’t status—it’s story.

9. Leather Belt (To Match Your Shoes)
Clean, polished, and unbranded. Often older than the car you drive.

10. Pocket Square (White Linen or Subtle Print)
Optional, but never overly styled. It should look like you just tucked it in absentmindedly—and still got it perfect.

🧳 Beyond the Closet

11. A Well-Cut Overcoat
Camel hair or navy wool. Worn winter after winter, often inherited, always admired.

12. The Barbour or Tweed Jacket
Weathered, lived-in, practical. For weekends in the country or long walks with the dog.

🪞 The Philosophy Behind the Style

Old money style isn’t just about the clothing—it’s about how it’s worn. There’s an air of nonchalance to it. Things are fitted, but never tight. Quality is paramount, but logos are avoided. You dress not to impress, but to reflect an inner confidence that has nothing to prove.

Closing Thought
In an era dominated by overconsumption and fast fashion, the old money aesthetic is a welcome return to permanence. It’s about investing in fewer, better things—and letting your presence speak louder than your labels.

Here’s to dressing like a gentleman—one heirloom at a time.