Throughout history, several men have come to epitomise the essence of the Old Money style.
These icons have left an indelible mark on the fashion world, setting the standard for timeless elegance and sophistication.
Let’s examine some of the most influential Old Money style icons and the key elements that defined their signature looks.
| Style Icon | Signature Look |
|---|---|
| John F. Kennedy | Navy suits, oxford shirts, slim ties, wayfarers |
| Cary Grant | Tailored suits, white shirts, pocket squares, black leather shoes |
| Paul Newman | Oxford shirts, chinos, leather jackets, boots |
| Ralph Lauren | Polo shirts, cable-knit sweaters, tailored blazers, chinos |
| Steve McQueen | Tailored trousers, button-down shirts, motorcycle jackets, aviator sunglasses |
| The Duke of Windsor | Double-breasted suits, patterned ties, pocket squares, spectator shoes |
| Gianni Agnelli | Italian-tailored suits, spread-collar shirts, silk ties, leather loafers |
| Clark Gable | Double-breasted suits, white shirts, pocket squares, cufflinks |
| The Kennedy Brothers | Tailored suits, oxford shirts, classic accessories, loafers |
| John D. Rockefeller Jr. | Dark suits, white shirts, subtle accessories, classic footwear |
1. John F. Kennedy
Former U.S. President John F. Kennedy is perhaps one of the most recognisable Old Money style icons.
His Preppy, All-American look was characterised by tailored suits, often in navy or grey, paired with white shirts and slim ties.
Kennedy’s style perfectly blends East Coast sophistication and youthful charm, making him a sartorial role model for generations of men.
Signature look
Tailored Navy suits, oxford shirts, preppy ties, wayfarers
2. Cary Grant
Hollywood legend Cary Grant’s impeccable style made him an enduring fashion icon.
Known for his debonair charm and classic good looks, Grant’s Old Money wardrobe was a masterclass in understated elegance.
Grant sported well-fitted suits in various colours, from traditional navy and grey to more daring shades like burgundy and green.
His attention to detail, from the cut of his suits to the polish of his shoes, set him apart as a true style icon.
Signature look
Tailored suits, impeccable white shirts, pocket squares, black leather shoes
3. Paul Newman
Actor Paul Newman’s style perfectly blended rugged masculinity and old-money refinement.
Newman effortlessly combined classic pieces like oxford shirts and chino trousers with casual leather jackets and boots.
Newman’s style was a testament to the power of simplicity, proving that a few well-chosen pieces can create a timeless, iconic look.
Signature look
Oxford shirts, chinos, leather jackets, boots
4. Ralph Lauren
Fashion designer Ralph Lauren has built an empire on the concept of Old Money style.
Lauren’s designs draw inspiration from the lifestyle of the American Preppies and their classic Ivy League style, featuring timeless pieces like cable-knit sweaters, tailored blazers, and polo shirts.
Lauren’s designs have become synonymous with the old-money look, making him a modern-day style icon.
Signature look
Polo shirts, cable-knit sweaters, tailored Preppy blazers, chinos
5. Steve McQueen
Actor Steve McQueen’s style perfectly balanced refinement and rebellious cool.
McQueen paired classic pieces like tailored trousers and button-down shirts with rugged elements like motorcycle jackets and aviator sunglasses.
McQueen’s effortless style and devil-may-care attitude made him an icon for generations of men.
Signature look
Tailored trousers, button-down shirts, motorcycle jackets, aviator sunglasses
6. The Duke of Windsor
The Duke of Windsor, formerly King Edward VIII, was a true Old Money style icon.
Known for his impeccable taste and innovative approach to fashion, the royal popularised trends like the Windsor knot and bold patterns in menswear.
The Duke’s style perfectly blended aristocratic elegance and daring individuality.
Signature look
Double-breasted suits, patterned ties, pocket squares, spectator shoes
7. Gianni Agnelli
Italian industrialist Gianni Agnelli was a true embodiment of the Old Money style.
Known for impeccable tailoring and unique personal touches, Agnelli’s style was a perfect blend of Italian sprezzatura and classic refinement.
The industrialist wore his watch over his shirt cuff and left his tie slightly askew, adding a nonchalant charm to his otherwise polished looks.
Signature look
Italian-tailored suits, spread-collar shirts, silk ties, leather loafers, and sprezzatura – a unique personal touch
8. Clark Gable
Hollywood legend Clark Gable’s style was a perfect example of old-money elegance.
Known for his dashing good looks and debonair charm, Gable often sported well-fitted suits, white shirts, and classic accessories like pocket squares and cufflinks.
Gable’s style was a testament to the power of timeless simplicity and effortless sophistication.
Signature look
Double-breasted suits, white shirts, pocket squares, cufflinks
9. The Kennedy Brothers
In addition to John F. Kennedy, his brothers Robert and Edward were known for their impeccable old-money style.
The Kennedy brothers often sported classic preppy looks, featuring tailored suits, oxford shirts, and timeless accessories like watches and cufflinks.
Their style was a perfect blend of East Coast refinement and All-American charm.
Signature look
Tailored suits, Oxford shirts, classic Preppy style ties and belts, penny loafers
10. John D. Rockefeller Jr.
Industrialist and philanthropist John D. Rockefeller Jr. was a true Old Money style icon.
Known for a conservative and traditional approach to fashion, Rockefeller sported dark, well-fitted suits, paired with white shirts and subtle accessories.
Rockefeller’s style was a testament to the power of understated elegance and the importance of quality craftsmanship.
Signature look
Dark navy suits and overcoats, white or light pink shirts, black Oxford shoes
Beyond Old-Money Fashion Icons
Before you go, here’s one of the best-kept secrets in men’s styling circles, a secret that only a few expert image consultants know or are willing to share.
First and foremost, professional styling requires knowing your unique body shape and seasonal colour palette, as the main factors in choosing perfectly fitting clothes in colours that complement your skin, eyes, and hair.
Only then you can be styled by occasion, location, season, and time of day, with garments, footwear, and accessories from heritage fashion brands that depict an old-money style gentleman of high confidence and success.
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1. Find Your Body Shape
Different garments flatter different physiques, so knowing your body shape is the first step in dressing like a confident man – free body shape quiz for men.
Once you know your unique body shape, take the second free quiz to discover your unique colour palette.
2. Find Your Unique Colour Palette
Remember, fashion comes in various colours, but not every hue complements your natural colour.
Take our free seasonal colour quiz for men to find the most suitable colours for you.
3. Find Your Ideal Fashion Style
By now, you should already know your body shape and unique colour palette; the next step is to discover your ideal personal fashion style.
The fastest and simplest way is to take our free fashion style quiz for men; it includes your ideal style, outfit ideas, relevant fashion brands, and much more.
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Remember, owning luxury clothes isn’t enough; to look stylish, confident, and successful, you must first know your body shape and colour palette and only then style by occasion, location, season, and time of day.
Contact us today and save headaches, time, and money; the first styling assessment is on us!
It’s time to show the world the confident and successful you, a gentleman of exquisite fashion taste.