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 elevate the ensemble and exude the refined charm associated with 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.
Oxford Shoes
Distinguished by their closed lacing system, sleek silhouette, and minimalist design, Oxfords are the epitome of formal footwear.
Formal Affairs
For black-tie events or gala dinners, nothing matches the elegance of polished black Oxford shoes.
Choose shoes from high-quality calfskin leather, which develops a rich patina over time.
Outfit Idea
- Black wool tuxedo with peaked lapels
- White cotton piqué dress shirt with French cuffs
- Black silk bow tie
- Black silk cummerbund
- Black patent leather Oxford shoes
- Black silk dress socks
Styling Tips
- Avoid shoes with excessive embellishments or detailing that can detract from the classic look.
- Choose thin, waxed laces in a color matching your shoes for a cohesive appearance.
- Wear over-the-calf socks in a color similar to your trousers to create a seamless, uninterrupted line.
Recommended Brands
- Church’s, John Lobb, Edward Green
Style Icons
Daniel Craig and Prince William showcase the power of impeccably tailored suits paired with polished Oxfords.
Brogues, Loafers, and Derby Shoes
Brogues, loafers, and derby shoes are ideal for pairing with chinos or dress trousers.
Brogues’ perforated patterns add visual interest and texture to any old money-inspired outfit.
Loafers, with their slip-on design and moccasin-like construction, are the most relaxed of all.
Derby shoes have an open lacing system and a slightly more relaxed silhouette than Oxford shoes.
Business Casual
Navigating the nuances of business casual can be a sartorial challenge, but the right footwear sets the tone.
Outfit Idea
- Navy wool blazer
- Light blue cotton dress shirt
- Burgundy silk tie with a small geometric pattern
- Khaki wool dress trousers
- Dark brown leather Derby shoes
- Navy cotton dress socks
- White linen pocket square
 
Styling Tips
- Choose shoes in rich colors like oxblood, dark brown, or chocolate to add depth to your outfit.
- Ensure your trousers are well-fitted and have the appropriate length and break to complement your shoes.
- Experiment with different leather finishes, such as pebbled or suede, to add dimension to your look.
Recommended Brands
- Crockett & Jones, Carmina, Allen Edmonds
Style Icons
Matt Bomer and Prince Carl Philip of Sweden demonstrate the art of blending luxury and casualness with well-chosen footwear.
Smart Casual
For smart casual occasions, where personality and comfort intersect with formality, suede or pebbled leather loafers or brogues are the perfect choice.
Colors like navy, forest green, or burgundy inject a personal touch into your ensemble, adding visual interest and a relaxed feel to your outfit.
Outfit Idea
- Brown tweed sports coat with a subtle check or houndstooth pattern
- Light pink cotton Oxford shirt
- Navy chinos or dark blue wool pants
- Dark brown leather penny loafers
- Light brown leather belt
Styling Tips
- The texture and color of your shoes add interest and character to your outfit.
- Match the formality of your shoes with the rest of your outfit to create a cohesive look.
- Don’t be afraid to mix textures, such as suede loafers with knit ties or wool blazers.
Recommended Brands
- Alden, Tricker’s, Cheaney & Sons
Style Icons
Eddie Redmayne and Ryan Reynolds showcase the art of smart casual styling with their eclectic yet sophisticated shoe choices.
Men’s Dress Shoe Mastery with The VOU
Mastering the art of dress shoe styling is key to achieving the Old Money aesthetic.
Investing in high-quality shoes of timeless styles is the key to creating looks that exude refinement and sophistication.
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.
Dressing well is an investment in yourself, and with the right guidance and a commitment to quality, you’ll exude the sophistication and charm of the old-money aesthetic.
Find your unique style with The VOU’s fashion style analysis today, and let us be your trusted partner in your sartorial journey.
