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How to Choose and Style Old Money Dress Shoes By Occasion

With a focus on timeless traditional styles and exquisite quality of craftsmanship, the old money aesthetic has an understated elegance and sophistication.

However, wearing the correct dress shoes is paramount to ooze the refined charm of the Old Money style.

As seasoned stylists with years of experience helping gentlemen master the art of dressing well, we’re here to show you the best dress shoes for each occasion.

1. Formal Events

For formal occasions such as black-tie events like gala dinners, nothing matches the elegance of polished black Oxford shoes.

Oxford Shoes

Distinguished by a closed lacing system, sleek silhouette, and minimalist design, Oxford shoes are the epitome of formal footwear and a must-have in Old Money looks.

Opt for high-quality calfskin leather, which develops a rich patina over time, adding character to your shoes.

Old Money style Oxford dress shoes
Oxford Shoes

Outfit Idea and Styling Tips for Oxford Shoes

Formal event? Nothing compares to the timeless elegance of a well-tailored black wool tuxedo with peaked lapels.

Old Money style Oxford dress shoes outfit idea

Pair this with a crisp white cotton piqué dress shirt featuring sophisticated French cuffs, and complete the look with a black silk bow tie and cummerbund.

Your choice of footwear is crucial – opt for polished black patent leather Oxford shoes, and remember to select thin, waxed laces that match the color of your shoes for a cohesive appearance.

Old Money style Oxford dress shoes outfit idea

To ensure a seamless, uninterrupted line, choose black silk dress socks that extend over the calf in a color similar to your trousers.

Old Money style Oxford dress shoes outfit idea

Avoid any excess embellishments or detailing on your shoes, as this can detract from the classic, refined look you aim to achieve.

Remember, the key to mastering the Old Money aesthetic is understated elegance.

Church’s, John Lobb, Edward Green, Crockett & Jones, and Gaziano & Girling are renowned for their exceptional craftsmanship and timeless designs.

Style Icons

Daniel Craig and Prince William showcase the power of impeccably tailored suits paired with polished Oxfords, demonstrating that simplicity is the ultimate sophistication.

2. Business-casual Events

Navigating the nuances of business casual can be a sartorial challenge, but the right footwear sets the tone. Opt for shoes that strike a balance between professionalism and comfort.

Brogues and Loafers

Paired with chinos or dress trousers, Brogues and Loafer style shoes are best for business casual meetings.

Brogues’ perforated patterns add visual interest and texture to any business casual outfit and create an old-money feel.

The intricate detailing showcases the craftsmanship and adds a touch of sophistication to your ensemble.

Business casual Old Money style Brogues shoes

On the other hand, Loafers’ slip-on design and moccasin-like construction make them ideal for Preppy-inspired business casual attire.

They offer a relaxed yet polished look, perfect for transitioning from the office to after-work events.

Business casual Old Money style Loafers

Outfit Idea and Styling Tips for Loafers

For business-casual events, a brown tweed sports coat with a subtle check or houndstooth pattern is a fantastic choice.

Old Money Style dress loafers

Pair the coat with a light pink cotton Oxford shirt, navy chinos or dark blue wool pants, and brown leather penny loafers.

Remember, the texture and color of your shoes can add interest and character to your outfit, so don’t be afraid to mix textures, such as suede loafers with knit ties or wool blazers.

Old Money Style dress loafers

Just be sure to match the formality of your shoes with the rest of your outfit to create a cohesive look.

Complete this ensemble with a light brown leather belt for a polished and fresh Old Money appearance.

Consider adding a pocket square or a subtle patterned sock to inject a touch of personality into your outfit.

Alden, Tricker’s, Cheaney & Sons, and Carmina offer a wide range of brogues and loafers that combine style, comfort, and durability.

Style Icons

Eddie Redmayne and Ryan Reynolds showcase the art of smart casual styling with their eclectic yet sophisticated shoe choices, proving that attention to detail can elevate any outfit.

3. Smart-casual Events

Suede or pebbled leather derby shoes are perfect for smart casual events, where personality and comfort intersect with formality.

Colors like navy, forest green, or burgundy inject a personal touch into your ensemble, adding visual interest and a relaxed feel to your outfit.

Don’t be afraid to experiment with different textures and colors to create a unique look that reflects your personal style.

Derby Shoes

The shoes’ open lacing system makes Derbies a slightly more relaxed footwear than the classic Oxfords.

The shoe’s versatility allows them to be dressed up or down, depending on the occasion.

Business casual Old Money style derby shoes
Derby Shoes

Outfit Idea and Styling Tips for Derby Shoes

When dressing for a smart-casual occasion, start with a navy wool blazer and a light blue cotton dress shirt.

Add a touch of color and pattern with a burgundy silk tie featuring a small geometric design.

Old Money Style dress Derby shoes

Match with dark brown leather Derby shoes and well-fitted chinos that complement your shoes.

Old Money Style dress Derby shoes

Don’t be afraid to experiment with different leather finishes, such as pebbled or suede, to add dimension to your look.

For a polished, sophisticated appearance, complete the outfit with navy cotton dress socks and a white linen pocket square.

To complete the Old Money aesthetic, consider adding a braided leather belt or a vintage-inspired watch.

Crockett & Jones, Carmina, Allen Edmonds, and Meermin offer a wide selection of derby shoes in various colors and finishes, catering to different tastes and budgets.

Style Icons

Prince Carl Philip of Sweden and Matt Bomer demonstrate the art of blending luxury and casualness with well-chosen footwear, showcasing how the right pair of shoes can tie an entire outfit together.

Men’s Dress Shoe Mastery with The VOU

Mastering the art of dress shoe styling is key to achieving the Old Money aesthetic.

At The VOU, our expert stylists are dedicated to helping you navigate the world of classic footwear and ensure that you always step out in style.

Whether you’re attending a formal gala, a business meeting, or a relaxed social gathering, we’ll guide you in selecting the perfect pair of dress shoes to complement your ensemble.

Find your unique style with The VOU’s fashion style analysis today, and let us be your trusted partner in your sartorial journey.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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