The Old Money Winter Shoe Guide for Men

Welcome to this winter’s style update. This season, we’re focusing on the best old-money shoes - timeless, high-quality, and built to last.

Old-money style isn’t about flashy logos. It’s about quiet confidence, heritage brands, and classic craftsmanship that looks even better with age.

What Makes a Shoe “Old Money”?

Old-money footwear has a few key traits:

• Quality leather - looks better the more you wear it.

• Classic shapes - like loafers, brogues, and Chelsea boots.

• Neutral colours - black, brown, tan, or oxblood.

• No loud branding - the craftsmanship speaks for itself.

• Durability - they last through many winters.

Best Winter Shoe Picks

1. Red Wing 3190 Chelsea Boots

A true heritage choice. Tough American leather, sleek silhouette - ideal for city winters.

2. Barbour Patton Chelsea Boots

Classic British style. Perfect with wool trousers and a tailored coat.

3. Blundstone 566 Thermal Boots

Warm, waterproof, and minimal. Great for cold, practical days.

4. Timberland Larchmont Chelsea Boots

Smart yet rugged. Ideal for weekends or casual winter outings.

5. Old Money Leather Dress Shoes

Perfect for formal events or dinners. Understated, polished, timeless.

How to Style Them

• City Days:
  Go for dark Chelsea boots with wool trousers and a camel overcoat.

• Casual Weekends:
  Pair Blundstones or Timberlands with chinos, a cashmere sweater, and a pea coat.

• Evenings or Events:
  Swap to leather dress shoes with tailored trousers and a blazer.

Final Tip

If you want your style to feel truly “old money,” buy fewer, better shoes.
Keep them clean, polish them regularly, and they’ll serve you beautifully for years.