The 6 Best Old Money Shoes for Men - Oxfords, Monk Straps, Chelsea Boots and Suede Loafers

The 6 Best Old Money Shoes for Men

Are you ready to elevate your footwear game with timeless sophistication? In The 6 Best Old Money Shoes for Men, we dive into the epitome of classic elegance. This guide is your ticket to mastering the art of old money style from the ground up.


We’ll explore iconic shoe styles like oxfords, monk straps, loafers, and Chelsea boots, dissecting their timeless appeal and revealing insider tips on how to effortlessly incorporate them into your wardrobe. Get ready to step into a world where every stride exudes refinement and charm.

Which are the best Old Money Shoes for Men?

1. Oxford Shoes: The Old Money Essentials

The Oxford shoe stands as a cornerstone in the Old Money wardrobe, embodying timeless elegance. Opt for black calf leather to seamlessly pair with your suit for a timeless look on formal occasions. Alternatively, introduce versatility with dark brown leather for a refined twist. For more casual events, embrace dark brown or black suede Oxfords, offering a relaxed yet polished look when paired with chinos or less formal attire.

2. Monk Strap Shoes: For A Sophisticated Touch

A pair of monk strap shoes will elevate your Old Money footwear collection, ideal for both formal and semi-formal events. Their distinct buckle closures exude style, adding a sophisticated touch to any ensemble. Like Oxford shoes, opt for classic black or dark brown hues in calf leather or suede for versatility. Whether paired with a suit for business affairs or dressed down with chinos for social gatherings, monk strap shoes effortlessly blend timeless charm with modern flair.

3. Leather Loafers: The Versatile Old Money Classics

Leather loafers epitomize comfort and versatility in the Old Money wardrobe. Ideal for various occasions, they seamlessly transition from formal suiting to smart-casual ensembles. Essential additions include the classic penny loafer and the sophisticated tassel loafer, each offering distinct style nuances. Whether paired with a tailored suit for formal gatherings or matched with chinos for a relaxed elegance, leather loafers embody the timeless charm and adaptability synonymous with Old Money sophistication.

4. Chelsea Boots: The Winter Season's Favorite

The Chelsea boots represent another important element of the Old Money style. They offer both everyday practicality and timeless elegance, and will be a favourite for the fall, winter, and spring seasons. Versatile enough to complement a variety of casual and semi-formal ensembles, owning them in both leather and suede will allow you to match them effortlessly with different outfits. Opting for classic colours like black and dark brown ensures seamless integration into the Old Money wardrobe.

5. Suede Loafers: The Old Money Shoes for Summer

The Suede Loafers are a masterpiece for the summers. It’s elegant and refined yet breathes well and will seamlessly match with light summer ensembles like chinos, linen, or blazers. These loafers will be both your everyday shoes for the summer, to your go-to companion for semi-formal summer occasions. Notably, suede loafers offer a larger flexibility in colour choices than other Old Money shoe styles. This allows for experimentation with suede loafers in colours such as navy, light beige, or light blue options that harmonize with the overall attire without overpowering it.

6. White Sneakers: For The Casual Everyday Outfit

White sneakers serve as a staple in the most casual Old Money style ensembles. However, when choosing sneakers, it’s crucial to opt for a clean design in white leather to maintain a refined aesthetic. These sneakers effortlessly complement everyday outfits, lending a touch of relaxed sophistication to your look.

FAQ - Frequently Asked Questions

What brands are best for Old Money Shoes?

The key when choosing a brand for your Old Money shoes is to choose a brand with timeless and sophisticated designs and high-quality materials. Classic Old Money brands that fulfill these values are for example:


  1. Loro Piana
  2. Myrqvist
  3. Morjas
  4. Velasca
  5. Aurélien

Which colors are best for Old Money shoes?

When selecting colours for Old Money shoes, adhere to tradition. Opt for black or dark brown leather for formal occasions, ensuring a classic and sophisticated appearance. For casual gatherings, embrace suede in black or dark brown, exuding relaxed refinement. In the summer, lighter-colored suede loafers in beige, navy, and light blue complement the season’s attire impeccably. Reserve sneakers for the most casual Old Money ensembles, favoring a pristine white design for a polished finish.

What are the best Old Money shoes for summer?

Choose suede loafers or clean white sneakers for more casual summer gatherings. For formal events under the sun’s warm embrace, elevate your style with classic Oxfords or leather loafers, ensuring a polished and distinguished appearance.

What are the best Old Money shoes for winter?

For formal events, choose the enduring elegance of Oxfords or Leather Loafers, exuding refined charm and grace. For the everyday and less formal gatherings, embrace the versatility of Chelsea boots. For casual outings amidst the winter frost, opt for the pristine allure of clean white sneakers, adding a touch of contemporary flair to your ensemble while maintaining the essence of classic refinement.

Want to learn more about the Old Money Style for Men?

Check out our guides The Ultimate Guide to Old Money Style for Men or The 12 Best Old Money Brands for Men more inspiration and fashion advice in the Old Money Style.