If you want to dress like a man of inherited wealth, you need more than expensive clothes.
Old money style is about tradition, heritage, and a quiet confidence that speaks through quality rather than trends.
Unlike flashy displays of luxury, old money fashion is refined, understated, and built to last.
In today’s styling guide, we will show you how to master the old money aesthetic as a young and stylish gentleman.
You’ll learn about essential wardrobe garments, footwear, and accessories from the most iconic brands, key styling principles, and see how style icons have defined this timeless look.
Whether you’re strolling through Mayfair, attending a country club gathering, or dining at a Michelin-starred restaurant, this is how you look like you belong.
What Exactly is Old Money Aesthetic
Old money fashion is a unique look based on an aesthetic that depicts inherited wealth, aristocratic heritage, and an unwavering commitment to tradition.
Unlike new money fashion, which focuses on ostentation and branding, old money fashion is understated, refined, and built on craftsmanship.
Every garment, footwear, and accessory reflects a legacy of quality and sophistication, worn not to impress but as a quiet declaration of status.
As a young man seeking to adopt the old money aesthetic, you must understand that genuine refinement is not achieved through visible luxury but through impeccable tailoring, high-quality materials, and a disciplined approach to style.
Old money men dress effortlessly, choosing garments that exude confidence, class, and social status rather than new money clothes that scream for attention.
Old Money Aesthetic Foundations
Old money men have perfected a dress code rooted in consistency, tradition, and quality.
Each garment, footwear choice, and accessory serves a purpose, and as a result, every outfit has a polished, statement vibe while retaining an understated, subtle luxury feel.
The key to mastering this aesthetic is understanding the fundamental principles that define true elegance, such as:
Highly Tailored Garments
Nothing communicates refinement like a perfectly tailored suit, blazer, or pair of trousers.
Old money men have their garments made-to-measure or bespoke, ensuring that every seam and silhouette is precise.
Brands like Huntsman, Henry Poole, and Anderson & Sheppard are the gold standard for bespoke tailoring, crafting garments that last a lifetime.
Only from Natural Fabrics
Wool, cashmere, linen, and Egyptian cotton define old money wardrobes.
These natural fibres provide superior durability, breathability, and an unmistakable touch of luxury.
Brands like Loro Piana and Brunello Cucinelli produce some of the finest cashmere and wool garments, ensuring timeless appeal and comfort.
In the Exact Old Money Colour Palette
Navy, charcoal, grey, beige, forest green, and camel dominate the old money wardrobe.
These classic old money colours create a sophisticated and versatile foundation, allowing effortless combinations without resorting to trends or flashy elements.
Without Any Logos
Old money men favour brands recognised for their heritage and craftsmanship rather than their logos.
Labels like Ralph Lauren Purple Label, Rubinacci, and Crockett & Jones create garments, tailoring, and footwear that speak through quality rather than branding.
True luxury never requires a visible label.
Old Money Wardrobe Essentials
Building your own old money capsule wardrobe requires a curated selection of garments, footwear, and accessories that reflect refinement, tradition, and stylistic longevity.
Every piece must be impeccably tailored, crafted from the finest materials, and chosen with a deep understanding of elegance.
The old money aesthetic is defined by consistency, discretion, and timeless sophistication rather than passing trends or visible branding.
Blazers and Sports Jackets
Old money men never underestimate the importance of a well-structured blazer or a soft-shouldered sports jacket.
A single-breasted navy blazer with gold or horn buttons, cut from pure wool or cashmere, is the cornerstone of a refined wardrobe.
The blazer must have a natural shoulder construction, a slightly suppressed waist, and a length that covers the seat for proper proportion.
Sports jackets provide a more relaxed yet equally sophisticated alternative.
Traditional herringbone tweed, Prince of Wales check, and houndstooth patterns add depth and texture while maintaining quiet luxury.
Neapolitan unstructured blazers from Rubinacci or Kiton offer soft drape and ease of movement, while structured jackets from Ralph Lauren Purple Label or Anderson & Sheppard create a more polished silhouette.
Suits and Trousers
Old-money men never chase the latest fashion trends in suits but always choose timeless, classic styles.
For example, a two-button, single-breasted wool suit in navy or charcoal grey remains the ultimate expression of quiet elegance.
Unlike the slim, overly tailored suits favoured by new money, old money suits have a balanced cut, allowing for movement and longevity.
Canali, Huntsman, and Cesare Attolini craft suits with impeccable structure, while Savile Row tailors offer the ultimate bespoke excellence.
For less formal settings, double-breasted grey flannel or navy worsted wool suits exude effortless refinement.
Peak lapels and side vents add sophistication, while subtle details such as ticket pockets or hand-sewn Milanese buttonholes indicate superior craftsmanship.
Wool flannel, cavalry twill, and high-twist wool trousers in shades of grey, beige, and brown are essential for year-round versatility.
Flat-front designs with side adjusters ensure a tailored appearance without the need for a belt, preserving clean lines.
Pleated trousers from Pini Parma and The Armoury complement heavier winter fabrics with a more classic silhouette.
Oxford Shirts and Knitwear
A refined old money wardrobe requires a selection of white and light blue Oxford shirts, crafted from Sea Island cotton or fine poplin.
Spread collars, mother-of-pearl buttons, and hand-finished cuffs elevate these wardrobe staples. Turnbull & Asser, Charvet, and Emma Willis produce shirts that balance structure and softness, making them ideal for formal and semi-formal occasions.
For layering, fine-gauge cashmere sweaters, merino wool cardigans, and lightweight turtlenecks in neutral shades such as navy, camel, and grey provide warmth without bulk.
Loro Piana and Johnstons of Elgin lead in luxury knitwear, with refined textures that complement tailored trousers and casual chinos.
Footwear
Old money footwear is always polished, well-maintained, and free from excessive detailing.
Brown penny loafers, crafted from full-grain leather or suede, offer timeless versatility and can be worn with tailored and casual ensembles.
Alden, Crockett & Jones, and John Lobb produce some of the finest examples, with Goodyear-welted soles ensuring durability.
For more formal occasions, black cap-toe Oxford shoes in smooth calf leather provide the perfect finishing touch to a refined suit. Edward Green and Gaziano & Girling offer unparalleled craftsmanship, ensuring a sleek silhouette with an impeccable shine.
For casual settings, suede chukka boots in dark brown or snuff suede maintain an air of sophistication while offering comfort.
Worn with wool trousers or well-fitted chinos, these boots embody relaxed elegance.
Brands such as Carmina, Berluti, and Drake’s create exceptional versions that easily balance formality.
Outerwear
The right outerwear is essential for maintaining a polished appearance in colder months.
A camel wool overcoat in a double-breasted cut exudes old-money elegance and pairs seamlessly with both suits and knitwear.
Iconic old money brands like Loro Piana, Burberry, and Private White V.C. produce some of the most refined options, blending warmth with classic tailoring.
For a more relaxed approach, wear navy pea coats with anchor buttons or tweed field jackets in earthy tones to create a subtle statement of inherited wealth.
Worn over a fine-gauge knit or Oxford shirt, these coats elevate even the most casual outfits.
Accessories
Old money accessories must be chosen with discretion and refinement, enhancing an outfit without overpowering it.
A vintage Rolex Datejust with a leather strap, a Cartier Tank with a gold case, or a Patek Philippe Calatrava represents the pinnacle of understated luxury.
Silk ties in regimental stripes, polka dots, or solid tones, sourced from Drake’s, Hermès, or Turnbull & Asser, add a refined touch to tailored ensembles.
Cufflinks in yellow gold or sterling silver, preferably inherited or monogrammed, provide subtle personalisation.
Leather belts in dark brown or oxblood, featuring simple gold or silver buckles, complement tailored trousers without drawing attention.
Swaine Adeney Brigg and Anderson’s produce timeless examples crafted from the finest materials.
During colder months, cashmere scarves in muted tones from Loro Piana or Johnstons of Elgin add warmth without excess.
Worn with a wool overcoat or a tailored blazer, these old money scarves reinforce the elegance of a well-assembled wardrobe.
Old Money Style Icons & Their Influence
Throughout history, certain men have exemplified the old money aesthetic through impeccable wardrobes, signature styling, and an elegant approach to fashion.
These men did not follow trends but instead defined a standard of dressing that remains relevant today.
Their legacy influences young men seeking to cultivate a wardrobe rooted in refinement, tradition, and quiet sophistication.
Cary Grant
Cary Grant remains one of the most referenced old money style icons, known for his impeccable tailoring, neutral colour palette, and unwavering commitment to classic menswear.
Every garment in Cary Grant’s wardrobe was meticulously chosen, fitting flawlessly without looking over-styled.
Grant’s signature look revolved around navy and charcoal single-breasted suits, crisp white or light blue dress shirts, and dark silk ties.
His preference for lightly structured shoulders, high armholes, and suppressed waists gave his suits a refined yet natural silhouette.
Rather than following trends, he focused on timeless designs with minimal detailing, ensuring his outfits always looked appropriate and sophisticated.
For casual settings, Grant preferred cream-coloured flannel trousers, navy blazers, and cashmere sweaters.
His eveningwear was equally distinguished, with midnight blue dinner jackets, patent leather Oxford shoes, and silk bow ties, all tailored to perfection.
By mastering the balance between structure and ease, Grant embodied effortless old money refinement.
Gianni Agnelli
Gianni Agnelli, the Italian industrialist and Fiat heir, personified old money elegance with a distinctive flair.
Unlike many of his aristocratic contemporaries, Agnelli introduced an air of sprezzatura—a studied nonchalance that made even the most tailored ensembles look natural and lived-in.
Agnelli’s wardrobe featured double-breasted navy blazers, wide-lapel grey flannel suits, and pleated wool trousers in earthy tones.
His ability to combine formality with an effortless attitude set him apart. He famously wore his wristwatch over his shirt cuff, left his tie slightly askew, and paired his bespoke suits with rugged hiking boots or driving shoes instead of traditional Oxfords.
Unlike rigid British tailoring, Agnelli preferred Neapolitan-style jackets with soft shoulders, unstructured construction, and a natural drape.
Brands such as Caraceni, Rubinacci, and Kiton tailored Agnelli’s suits, ensuring a perfect Italian style, elegance and comfort.
His use of silk knit ties, high-waisted trousers, and unbuttoned shirt collars under jackets created an effortless aristocratic look that continues to inspire modern interpretations of old money style.
Duke of Windsor
The Duke of Windsor, formerly King Edward VIII, was a trailblazer in men’s fashion, revolutionising the way aristocrats dressed.
While most of his contemporaries adhered to strict formal dress codes, the Duke introduced softer, more comfortable tailoring, subtly altering the course of old money style.
His personal wardrobe included Prince of Wales check suits, double-breasted blazers, and Fair Isle knitwear.
He pioneered the use of tapered trousers with high waists and forward pleats, eliminating the bagginess common in early 20th-century tailoring.
The Duke also popularised brown suede loafers and spectator shoes, proving that casual footwear could still be sophisticated.
His mastery of pattern mixing, particularly striped ties with plaid suits and checked blazers with solid wool trousers, redefined the aristocratic approach to dressing.
He frequently wore Ascot ties, silk pocket squares, and pinned collars, ensuring every detail of his outfit exuded refinement.
Tailors such as Scholte, Anderson & Sheppard, and Huntsman crafted his garments, setting new sartorial standards for high society.
Aristotle Onassis
Aristotle Onassis, the Greek shipping magnate, brought Mediterranean glamour to the old money aesthetic.
Unlike the reserved British aristocrats, Onassis favoured cream linen suits, open-collared shirts, and aviator sunglasses, blending refinement with an effortless summer elegance.
Onassis’s wardrobe was built around single and double-breasted linen jackets, silk shirts in neutral tones, and tailored wool trousers.
He loved pairing navy blazers with white trousers for a Riviera-inspired look, epitomising relaxed yet polished dressing.
One of his signature touches was his choice of bold accessories, including gold-rimmed Cartier aviators, silk scarves worn loosely around the neck, and handmade leather sandals or Belgian loafers.
This approach to styling was rooted in luxury but never ostentatious, ensuring that every outfit conveyed effortless wealth rather than forced extravagance.
Ralph Lauren
Ralph Lauren is not just a designer but a living embodiment of the American old-money aesthetic.
Although he built his fortune rather than inheriting wealth, Lauren mastered the nuances of aristocratic dressing, creating a brand that epitomises East Coast elegance.
His personal wardrobe mirrors the ideals of classic American wealth, blending Savile Row tailoring with Ivy League sportswear.
Lauren loves to wear navy blazers with brass buttons, cream cable-knit cashmere sweaters, and pleated flannel trousers.
His preference for suede driving shoes, leather duffle bags, and knitted silk ties reinforces American aristocracy’s relaxed yet luxurious style.
Ralph Lauren’s influence extends beyond his own wardrobe. In his Ralph Lauren Purple Label and Polo Ralph Lauren collections, he blends the British Sloane Ranger style with American Preppy, ensuring the old money style remains accessible yet aspirational.
How to Wear Old Money Style Without Looking Like You’re Trying
The key to old-money fashion is effortless elegance, so avoid over-styling or wearing head-to-toe branded designer clothes.
Mixing old heritage brands with newer artisans like The Armoury or Pini Parma keeps the look authentic.
Invest in alterations— even an off-the-rack blazer can look bespoke if it fits perfectly.
The Importance of Proportion and Fit
Achieving a refined appearance hinges on wearing clothing that complements your unique body shape.
Proper fit ensures comfort and exudes confidence, both hallmarks of the old money style.
Dress for Your Exact Body Shape: Understanding your body shape is crucial. Men body shapes fall into six core categories such as: triangle or pear, inverted triangle, rectangle or straight, oval or apple, trapezoid, or hourglass. Each shape has a specific silhouette that enhances your natural proportions when dressed correctly.
Wear Tailored Clothing: Invest in tailoring to ensure garments fit impeccably. For instance, men with a trapezoid body shape benefit from slim-fitted clothes and fitted blazers, while men with a rectangle shape should opt for structured tailoring and layered looks to add dimension.
Avoiding Modern Pitfalls That Dilute Old Money Style
To preserve the authenticity of the old money aesthetic, be mindful of contemporary fashion missteps:
Avoid Overly Trendy Clothes: Steer clear of fleeting fashion trends that can undermine the timelessness of your look. Instead, focus on classic pieces that have stood the test of time.
Subtle Branding: Eschew garments with conspicuous logos or branding. Old money style is characterized by understatement; the quality of your clothing should speak for itself without overt brand displays.
Mindful Accessorizing: Limit the use of flashy accessories. Opt for minimalistic, high-quality pieces that complement your outfit without drawing excessive attention.
Incorporate Luxury but Without Excess
Luxury in the old money context is about quality and subtlety rather than ostentation:
Choose Quality Fabrics: Select garments from superior materials like cashmere, fine wool, and high-grade cotton. These fabrics look better and last longer, embodying the old money preference for durability.
Invest in Timeless Pieces: Prioritize classic items such as a well-fitted navy blazer, tailored trousers, and quality leather shoes. These staples form the foundation of a versatile wardrobe that exudes quiet luxury.
Pay Attention to Details: Focus on the finer details, such as mother-of-pearl buttons, hand-stitched seams, and custom-tailoring. These subtle elements enhance the overall quality and appearance of your attire.
Final Thoughts
Creating your own old money style is less about embarking on a financial investment and more about cultivating an eye for timeless elegance and quality.
By understanding your body shape, avoiding modern fashion pitfalls, and incorporating luxury in a restrained manner, you can develop a capsule wardrobe that reflects heritage, taste, and refinement.
It is an approach ensuring that, whether you’re attending a formal event or enjoying a casual day out, you project the understated sophistication synonymous with true old money gentlemen.