Elegant old money shoes for men, showcasing timeless style and sophistication in classic designs and premium materials.
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The 6 Best Old Money Shoes for Men

Old money style is all about timeless elegance, quiet luxury, and fine craftsmanship. Unlike fleeting trends, it values quality over quantity and sophistication over flash. When it comes to shoes, old money shoes for men are essential for a well-dressed wardrobe, reflecting effortless style and lasting appeal.

This guide will explore the best old money shoes for men, from formal Oxfords to casual white sneakers, helping you choose the right footwear for any occasion.

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Formal Old Money Shoes for Men

Men's formal old money shoes featuring black leather and black laces, exuding elegance and sophistication.

Oxford Shoes: The Old Money Essential

Oxford shoes are the epitome of old money shoes for men. They have long been considered a symbol of class, tradition, and sophistication. Oxfords originated in the early 1800s in Scotland and Ireland, gaining popularity at Oxford University hence the name. Their simple, elegant design characterized by a closed lacing system makes them a go-to for anyone seeking a refined, polished look.

Why Oxford Shoes Are Synonymous with Old Money:

  • Refined and Structured: The sleek design of Oxfords exudes formality, making them perfect for business meetings, weddings, and other upscale events.
  • Versatility: Available in various colors and finishes, from classic black to rich oxblood, Oxfords can be paired with almost any outfit, whether a formal suit or a more casual ensemble.
  • Timeless Appeal: The beauty of Oxfords is that they never go out of style. The more worn-in they get, the more character they develop, which is why they remain a staple of old money fashion.

Best Oxford Brands for Old Money Style:

  • Crockett & Jones
  • Church’s
  • Edward Green

These brands are renowned for their attention to detail, quality leather, and meticulous craftsmanship, ensuring that every pair of Oxfords looks as elegant as it feels.

Where to Buy Oxford Shoes That Look Like Old Money

Finding Oxford shoes that embody the old money style requires searching for brands that prioritize craftsmanship. Look for leather rather than synthetic materials, and choose classic colors like black, dark brown, and oxblood for the most refined look. You can find these shoes at:

  • Nordstrom: A reliable retailer for high-end men’s footwear.
  • Shoe Snob: An online store dedicated to offering luxurious leather shoes, including classic Oxfords.
  • Berluti: For the ultimate in elegance, Berluti’s Oxfords are a must-see.
Two pairs of Oxford shoes in the same color, showcasing distinct styles reminiscent of classic elegance and old money aesthetics.

Monk Strap Shoes: For A Sophisticated Touch

If you’re looking to elevate your wardrobe beyond the traditional Oxford, Monk Strap shoes offer a sophisticated and distinctive alternative. These shoes are less formal than Oxfords but still retain the refined aura associated with old money style. Characterized by a single or double buckle strap, Monk Straps were originally worn by monks in medieval Europe and have since evolved into a symbol of modern refinement.

Why Monk Strap Shoes Appeal to Old Money:

  • Subtle Distinction: The buckle closure adds an interesting touch without sacrificing the shoe’s elegant appeal.
  • Comfortable yet Stylish: Unlike Oxfords, Monk Straps are often easier to slip on and off, making them ideal for those who want both comfort and sophistication.
  • Perfect for Smart-Casual Looks: Pair them with chinos or a tailored blazer for a polished yet relaxed outfit.

Best Brands for Old Money Monk Strap Shoes:

  • John Lobb
  • Santoni
  • Berluti

Casual Old Money Shoes for Men

While formal shoes like Oxford shoes are essential for an old money wardrobe, casual footwear also plays a key role in creating a refined yet relaxed aesthetic. Here are some of the best casual old money shoes for men:

Two images showcasing a man in brown shoes and another in tan shoes, exemplifying casual old money footwear for men.

Leather Loafers: The Versatile Old Money Classic

Leather loafers are one of the most versatile shoes you can own. They strike the perfect balance between casual and formal, making them ideal for both relaxed days at the office and weekend outings. The loafer’s slip-on design ensures ease and comfort, but its sleek leather finish retains a high-end look.

Why Leather Loafers Are Timeless:

  • Effortless Elegance: Leather loafers never try too hard; their subtle sophistication adds just the right amount of class to any outfit.
  • Year-Round Wearability: Leather loafers are perfect in every season—pair them with a suit in the cooler months or dress them down with chinos or shorts in the summer.
  • Wide Range of Styles: From penny loafers to tassel loafers, there’s a style to suit every old money wardrobe.

Where to Buy Leather Loafers for Old Money Style:

  • Gucci
  • Salvatore Ferragamo
  • Tod’s

Chelsea Boots: The Winter Season’s Favorite

As the temperatures drop, Chelsea boots become an essential part of an old money wardrobe. These boots, with their close-fitting elastic sides, offer both comfort and style, making them perfect for colder weather.

Brown and black Chelsea boots, perfect for the winter season, showcasing a stylish and versatile design

Why Chelsea Boots Are a Must-Have:

  • Understated Elegance: The sleek, minimal design of Chelsea boots adds sophistication without being flashy.
  • Versatility: They can be worn with jeans, chinos, or even suits, making them incredibly adaptable for different occasions.
  • Warmth and Comfort: The ankle-high style keeps your feet warm during the winter months without compromising on style.

Best Brands for Chelsea Boots:

  • Church’s
  • Cheaney
  • Saint Laurent

Suede Loafers: The Old Money Shoes for Summer

When the warm weather hits, suede loafers are the perfect choice for maintaining an old money look while staying cool. Suede has a more relaxed, laid-back vibe than traditional leather, but still retains that touch of luxury that’s crucial for old money style.

Black suede loafers featuring a gold buckle, embodying elegance and sophistication for a refined summer look.

Why Suede Loafers Are Ideal for Summer:

  • Breathability: Suede is lighter and more breathable than leather, making it a great option for hot weather.
  • Casual yet Polished: Pair suede loafers with a linen shirt and chinos for a refined summer look.
  • Soft and Comfortable: Suede offers a softer feel that’s perfect for all-day wear.

Where to Find Quality Suede Loafers:

  • Santon
  • Alden
  • Edward Green

White Sneakers: For the Casual Everyday Outfit

White sneakers have become a staple in modern old money style. Once reserved for athletic use, they’ve since evolved into a key part of the luxury wardrobe. When styled correctly, white sneakers can be both casual and refined, making them perfect for a relaxed yet polished look.

A woman in a black top and pants, complemented by white sneakers, showcasing a casual everyday outfit.

Why White Sneakers Are Part of the Old Money Aesthetic:

  • Sleek and Clean: A pair of simple white sneakers adds a crisp, fresh look to any outfit.
  • Versatile and Comfortable: Whether you’re pairing them with a blazer or jeans, white sneakers work for almost any occasion.
  • Understated Luxury: Look for high-end brands that offer minimalist designs with premium materials.

Best White Sneaker Brands for Old Money Style:

  • Common Projects
  • Gucci
  • Tod’s
A collection of men's branded shoes in various colors displayed against a vibrant background of red, blue, and yellow.

Which Are the Best Old Money Shoes for Men?

After discussing the top picks for both formal and casual styles, let’s recap the 12 best old money shoes for men.

Shoe TypeBest BrandsIdeal ForBest Colors/Materials
Oxford ShoesCrockett & Jones, Church’s, Edward GreenFormal occasions, business meetingsBlack, oxblood, dark brown
Monk Strap ShoesJohn Lobb, Santoni, BerlutiCasual to semi-formal looksBrown, black, dark tan
Leather LoafersGucci, Ferragamo, Tod’sVersatile, smart-casual styleTan, brown, black
Chelsea BootsChurch’s, Cheaney, Saint LaurentFall and winter styleBlack, dark brown, grey
Suede LoafersSantoni, Alden, Edward GreenSummer casual wearLight brown, navy, grey
White SneakersCommon Projects, Tod’s, GucciCasual everyday wearWhite leather

Conclusion

When it comes to old money shoes for men, the key is to focus on timeless, quality craftsmanship and versatile designs that never go out of style. Whether you’re looking for the perfect Oxford shoes, sophisticated Monk Straps, or laid-back suede loafers, each of these shoes adds a touch of elegance and refinement to your wardrobe.

Investing in these old money shoes is not just about fashion—it’s about making a statement. Choose wisely, and these shoes will serve you for years, always looking fresh and refined.

FAQs

What are the old money shoes called?

Old money shoes are typically classic styles like Oxfords, Brogues, Loafers, and Derby shoes, often made from high-quality leather.

What is the most expensive male shoe brand?

The most expensive male shoe brand is often considered to be John Lobb, with handmade luxury shoes costing thousands of dollars.

What shoes do girls like most on guys?

Girls tend to like classic, clean styles like Oxford shoes, loafers, and sleek sneakers—shoes that show sophistication and confidence.

What is trending in footwear for men?

Trending footwear for men includes chunky sneakers, minimalist designs, and sustainable or eco-friendly shoes, with a focus on comfort and style.

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