The Gentleman's Approach to Old Money Style
The old money aesthetic for men represents a timeless approach to style that prioritizes quality, fit, and understated elegance. Unlike fashion trends that come and go, this classic way of dressing has remained relevant for generations, communicating a sense of quiet confidence and refined taste. This guide explores the essential elements of old money style for the modern gentleman, offering insights into building a wardrobe that balances tradition with contemporary relevance.
The Foundation: Quality Tailoring
At the heart of old money style lies exceptional tailoring. A well-fitted navy blazer serves as perhaps the most versatile cornerstone of this aesthetic, easily paired with everything from grey flannel trousers to quality denim for a more casual approach. Invest in at least one made-to-measure suit in a classic navy or charcoal gray—these colors offer maximum versatility and will never fall out of favor.
The importance of proper fit cannot be overstated. Even moderately priced garments can look significantly more expensive when they fit perfectly. Shoulders should align with your natural shoulder line, jacket sleeves should reveal about half an inch of shirt cuff, and trousers should break slightly over your shoes. These subtle details communicate attention to detail and respect for tradition—hallmarks of old money style.
When selecting tailored pieces, pay close attention to construction details. Full canvas construction, hand-stitched lapels, and natural shoulder lines are worth the investment, as they contribute to both the appearance and longevity of the garment. Similarly, trousers should feature quality waistbands, proper lining at stress points, and clean finishing on all seams.
For those new to tailoring, start with versatile pieces that can be worn in multiple contexts. A navy blazer with brass or horn buttons, medium gray trousers, and a blue oxford cloth button-down shirt create a foundation that works for most occasions. As your wardrobe expands, consider adding subtle variations in texture and pattern while maintaining the classic color palette.
The Essential Pieces
Beyond tailoring, several key pieces define the old money wardrobe. Oxford cloth button-down shirts in white and light blue, cashmere sweaters in neutral tones, and well-made loafers or derby shoes in brown or black leather all contribute to this timeless aesthetic. For casual settings, polo shirts, quality denim, and boat shoes or suede loafers maintain the refined approach while offering comfort.
The oxford cloth button-down shirt (often abbreviated as OCBD) deserves special mention as perhaps the most versatile item in the old money wardrobe. Originally associated with polo players who buttoned down their collars to prevent flapping during play, this shirt style has become a staple of refined casual dressing. Look for versions made from substantial cotton with proper rolling collars and mother-of-pearl buttons.
Knitwear represents another cornerstone of the old money wardrobe. Cashmere sweaters in crew neck or V-neck styles offer luxurious warmth and sophisticated appearance, while cotton cable knit sweaters provide a more casual alternative with traditional appeal. Navy, burgundy, forest green, and oatmeal are classic color choices that pair easily with the rest of the wardrobe.
For outerwear, the old money aesthetic favors classic styles with heritage appeal. A well-made trench coat in khaki, a navy peacoat, or a waxed cotton field jacket all offer protection from the elements while maintaining the refined appearance. These pieces should be selected with an eye toward longevity, as they often improve with age, developing character through years of wear.
The Details Matter
Old money style is defined as much by what it avoids as what it includes. You'll notice a distinct absence of flashy logos, trendy silhouettes, or attention-seeking details. Instead, quality is communicated through subtle elements: hand-stitched buttonholes, horn buttons, canvassed jacket construction, and superior fabrics that improve with age.
Accessories follow the same principle of understated quality. A mechanical watch with a simple leather strap, sterling silver or subtle gold cufflinks for formal occasions, and a quality leather belt that matches your shoes complete the look without drawing undue attention. These items should be selected with care, as they often become signature pieces that complement a variety of outfits.
The old money approach to watches deserves particular attention. Rather than selecting the most expensive or recognizable timepiece, this aesthetic favors understated quality—perhaps a vintage Omega or JLC with a simple leather strap, or a modern interpretation of classic designs from heritage brands. The emphasis is on craftsmanship and discretion rather than obvious displays of wealth.
Even items that might seem inconsequential receive careful consideration in the old money wardrobe. Handkerchiefs in white linen or cotton, umbrellas with wooden handles and quality frames, and leather portfolios or briefcases all contribute to the overall impression of refined taste. These details may seem minor individually, but collectively they create a coherent aesthetic that communicates attention to quality and tradition.
The Color Palette and Patterns
The old money color palette for men tends toward the classic and understated. Navy, gray, khaki, white, and burgundy form the foundation, creating a cohesive wardrobe where pieces can be easily combined. This approach to color not only simplifies dressing but also ensures that investments in quality pieces will remain relevant regardless of seasonal trends.
When patterns are incorporated, they tend toward the traditional. Subtle pinstripes or chalk stripes for suits, regimental stripes for ties, tattersall checks for casual shirts, and argyle for knitwear all have historical associations with upper-class pursuits and institutions. These patterns should be incorporated thoughtfully, with attention to scale and proportion to maintain the overall sense of refinement.
The approach to combining patterns follows traditional rules that ensure harmony rather than discord. When wearing multiple patterns, vary the scale—perhaps a subtle pinstripe suit with a wider striped tie, or a tattersall shirt with a solid knit tie. This creates visual interest while maintaining the cohesive, intentional appearance that characterizes old money style.
Seasonal adjustments to the color palette maintain the classic approach while acknowledging practical considerations. Summer might bring lighter blues, stone, and cream, while fall and winter welcome deeper tones like olive, burgundy, and charcoal. Throughout these seasonal shifts, the emphasis remains on versatility and cohesion rather than trend-driven color choices.
Casual Elegance
While much of old money style focuses on tailored clothing, casual settings require their own approach to refined dressing. The key is maintaining the principles of quality and understatement while adapting to more relaxed contexts. This might mean well-fitted chinos or quality denim paired with an oxford shirt or polo, perhaps with a cashmere sweater or unstructured sport coat depending on the occasion.
Weekend wear in the old money tradition emphasizes comfort without sacrificing refinement. Quality denim in straight or slim (but not skinny) cuts, paired with oxford cloth button-downs or well-made polo shirts, creates a casual look that maintains the overall aesthetic. Footwear might include suede loafers, boat shoes, or quality sneakers from heritage brands—all selected for their combination of comfort and classic design.
Even in the most casual settings, attention to fit and quality remains paramount. T-shirts should be made from substantial cotton with clean finishing, shorts should hit just above the knee in classic styles, and sweats or athletic wear should be reserved for actual athletic pursuits rather than everyday casual wear. This disciplined approach to casual dressing distinguishes old money style from more relaxed or trend-driven aesthetics.
The concept of appropriate dressing—selecting attire suited to the specific context—is central to old money style. This means understanding the subtle gradations between different levels of formality and having the wardrobe versatility to respond appropriately. A Sunday brunch might call for chinos and an OCBD with loafers, while a country weekend might incorporate more rugged elements like waxed cotton jackets or heritage knitwear.
Investing Wisely
Building an old money wardrobe represents a significant investment, but one that pays dividends over time through longevity and versatility. For those beginning this journey, focus first on foundational pieces that offer maximum versatility: a navy blazer, gray flannel trousers, oxford cloth button-downs in white and blue, and quality leather shoes in classic styles.
Understanding where to allocate resources is crucial. Invest most heavily in items where quality is immediately apparent and longevity is essential—tailored jackets, outerwear, shoes, and accessories like watches. Items closer to the skin, like shirts and knitwear, can be replaced more frequently and might warrant a more moderate investment, though quality should never be compromised entirely.
Maintenance forms an essential component of the old money approach to clothing. Learning proper care techniques—how to polish shoes, store knitwear, or maintain tailored clothing—extends the life of investments while preserving their appearance. This attention to maintenance reflects the broader value placed on stewardship and preservation rather than constant replacement.
The old money approach to style offers more than aesthetic benefits; it represents a more sustainable and satisfying relationship with clothing. By investing in quality pieces that transcend trends, maintaining them properly, and developing a personal style rooted in classic principles, men can create wardrobes that serve them well for decades while communicating a sense of refined taste and quiet confidence.