Princess Diana Old Money Style

Old Money outfits are a beacon of fine details, subtle luxury, and timeless elegance in the ever-changing world of fashion and seasonal trends.

‘Old Money’ echoes a heritage of wealth passed down through generations, showcased by a fashion style that values quality, tradition, refinement, and understated luxury.

In this article, I’ll introduce you to 10 Old Money outfits curated by our stylists to depict a legacy of elegance, quiet sophistication, timeless appeal, craftsmanship, and true class.

1. Classic Sloaner (with a Cape Cod Twist)

Princess Diana Old Money Style
Princess Diana’s Old Money Style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style


Lady D’s ‘Classic Sloane’ outfit impeccably illustrates the Old Money look by blending the high-society elegance characteristic of the Sloane Ranger style with touches of casual sophistication of New England’s Cape Cod aesthetic.

Start with a white turtleneck as a versatile foundation, suitable for various occasions, from casual outings to formal events, and a khaki green double-breasted blazer.

The blazer must have a structured silhouette and military-inspired color influenced by traditional British tailoring, a staple in the Sloane Ranger wardrobe.

Match it with white fitted chino pants – a nod to Preppy coastal attire associated with maritime New England locales like Cape Cod – to balance the blazer’s color.

Wear brown leather two-tone loafers, long favored in Old Money fashion as the epitome of timeless footwear and sophistication; the two-tone design is a subtle nod to the equestrian roots celebrated in Old Money circles.

Accessorize with 70s-style oversized square sunglasses for an air of retro mystery and a canvas and leather tote bag to depict a life of leisure, modernity, and luxury.

2. Riviera Chic

Claudia Schiffer Old-Money styleClaudia Schiffer Old-Money style
Claudia Schiffer’s Old-Money style

Claudia Schiffer Old-Money styleClaudia Schiffer Old-Money style

Claudia Schiffer’s Riviera-inspired outfit is built around two white, simple, and elegant pieces relevant to the leisurely, luxurious lifestyle of the Riviera: a rib knit T-shirt and an A-line skirt.

The skirt’s shape flatters the figure while depicting a polished 1960s vibe, perfect for a summer day at a seaside resort or an upscale brunch.

The outfit is complemented by white pointed-toe pumps, an artisanal toggle belt, a silk headscarf, and white oval sunglasses that conjure images of Old Hollywood glamour and Riviera luxury.

Complete the look with a small basket made of wicker with a braided pattern reminiscent of the Mediterranean pastoral chic vibe, showing that the Old Wealth style is always in harmony with nature.

3. American Preppy Explorer

Melania Trump Old-Money StyleMelania Trump Old-Money Style
Melania Trump’s Old-Money Style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Melania’s American Preppy Explorer look blends the French sophistication of BCBG style with the clean-cut of American Preppy in a look crafted for the modern woman who appreciates the legacy of Old Money fashion while embracing the spirit of adventure.

Start your outfit with a double-breasted khaki linen blazer in homage to the traditional safari jackets donned by explorers in the African bush but tailored to fit the contemporary BCBG aesthetic: sharp, sleek, and chic.

Match it with a white pleated front short-sleeve shirt, white wide-leg linen pants, and classic ballet flats ideal for the leisurely aesthetics of Old Money attire.

Accessorize with a black leather skinny belt, a gold buckle typical of BCBG’s attention to detail, and a Panama hat, the quintessential accessory for any safari-inspired ensemble.

4. BCBG Power-dressing

Amal Clooney Old Money styleAmal Clooney Old Money style
Amal Clooney’s Old Money style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Centered around Chanel’s iconic piece favored by the BCBG and Upper East Side elite, Miss Cloony’s BCBG outfit pays homage to the Parisian aristocracy and heritage-rich British countryside.

Start with a cropped tweed suit jacket and a tailored-fit tweed skirt depicting the British Country Club style influence on Old Money fashion.

The skirt’s tailored fit and modest length are hallmarks of the traditional ‘Old Money’ style, exuding a commanding elegance.

Wear black leather court shoes, a universal symbol of polished professionalism and a cornerstone in the wardrobes of women who frequent the halls of power and prestige, resonating with the Preppy emphasis on neatness and formality.

Accessorize with retro-inspired cat-eye sunglasses suggesting the classic film star elegance that has permeated upscale fashion since the ’60s and a black leather kiss lock handbag for a touch of vintage glam.

5. Nautical Preppy

Kate Middleton Old Money styleKate Middleton Old Money style
Kate Middleton’s Old Money style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Kate’s Nautical-inspired outfit is a harmonious blend of casual maritime attire and refined Preppy style, depicting a look suitable for a yachting day or a leisurely afternoon at the resort.

The centerpiece is the Breton stripe jumper – initially worn by French sailors and later a key navy attire – now a staple in the Preppy wardrobe, complemented by seafaring shorts with gold buttons reminiscent of the smart attire characteristic of the British Country Club style.

Match with white canvas sneakers, relevant in the wardrobes of affluent coastal communities, and accessorize with small hoop earrings, a subtle but timeless piece of jewelry that offers a hint of sophistication without overpowering the outfit’s relaxed, coastal vibe.

6. Modern Equestrian

Zendaya Old Money styleZendaya Old Money style
Zendaya’s Old Money style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Zendaya’s outfit channels the Equestrian style, a look core to the Old Money aesthetic thanks to its embodiment of tradition, heritage, and silent wealth.

Start with a wool houndstooth double-breasted blazer with gold buttons and waistcoat over a ruffle collar blouse in a look that blends the heritage of equestrian attire with the prestige of military-inspired attire.

Inspired by the English aristocracy’s countryside horse riding, hunting, and outdoor activities, this aesthetic is paramount in the wardrobes of country homes and private clubs.

Pair with black dress pants reflecting the sartorial sharpness and practical elegance characteristic of the Ivy League style and black leather pumps, a staple in Old Money fashion.

Accessorize with a neck scarf with a brooch featuring a family crest for a final touch of finesse characteristic of Old Money fashion.

7. Urban Preppy

Karlie Kloss Old Money StyleKarlie Kloss Old Money Style
Karlie Kloss’s Old Money style

Karlie Kloss Old MoneyKarlie Kloss Old Money

Karlie’s Old Money outfit is a contemporary take on the classic Preppy style, tailored for the city environment.

Start with a nautical-look double-breasted striped blazer reminding of the leisurely coastal lifestyles and a black turtleneck sweater, a staple in the Preppy and BCBG wardrobes but adapted here for an urban setting.

Pairing with straight-cropped jeans and pointed-toe ballet flats will create a blend of formality and practicality, characteristic of Old Money attire.

Completed with small hoop earrings representative of BCBG styling and a black leather tote bag, another common theme in Old Money fashion.

8. Countryside Attire

Kelsey Merritt Old Money styleKelsey Merritt Old Money style
Kelsey Merritt’s Old Money style (image courtesy @kelseymerritt)

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Kelsey’s outfit blends the essence of countryside elegance with elements characteristic of the classic equestrian style.

Start with a white Oxford button-down shirt, a Preppy symbol of classic sophistication, and traditional white chino pants, ideal for countryside settings, where comfort meets style.

Layer with a cable knit sweater, and cinch the waist with skinny leather to create a heritage-inspired look as much at home in a country lodge as at an upscale outdoor gathering.

Solidify the countryside theme with Wellington boots to embody the rural chic associated with the affluent at leisure and a leather hobo bag fitting for leisurely afternoons at a countryside estate.

9. Country Club Casual

Edita Vilkeviciute Old Money styleEdita Vilkeviciute Old Money style
Edita Vilkeviciute’s Old Money style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

By blending traditional Preppy attire with modern athleisure, Edita’s Old Money outfit is a trendy interpretation of the classic country club casual style.

Start with a V-neck tennis top and tennis shorts, indicative of the sporty yet elegant apparel of the tennis courts and golf courses of upscale country clubs.

Wear a single-breasted blazer over the sporty base to lend an air of formality and transform the outfit into a look ready for the social spaces of a country club.

Accessorized with a horse-bit buckle leather belt to add an equestrian flair, layered gold bracelets for a subtle display of luxury, and white sneakers with striped crew socks, in line with the neat, clean-cut aesthetic of country club fashion.

10. Nautical BCBG

Ivanka Trump Old Money styleIvanka Trump Old Money style
Ivanka Trump’s Old Money style

10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style10 Old Money Outfit Ideas to Dress in a Timeless Quiet-Luxury Style

Ivanka’s outfit is a charming fusion of BCBG style with Nautical aesthetics in a refined look for the discerning woman.

Start with a white round-neck blouse and a double-breasted light-blue blazer in a nautical color palette, formal silhouette, and belted waist to pay homage to the coastal influences of the Preppy style.

Match it with sky blue pumps to complement the blazer’s hue and continue the maritime theme, and white chino pants to maintain the relaxed feel, characteristic of leisure wear in high-end resort towns and yachting clubs.

Accessorize with a pearl brooch, jewelry emblematic of Old Money’s timeless taste, and a white leather tote bag to create an outfit perfect for an upscale seaside brunch or an afternoon aboard a luxury yacht.

About Old Money Style

Rooted in the aristocratic lifestyles of the elite, Old Money outfits offer a glimpse into a legacy of timeless fashion and understated, minimalist luxury.

The Old Money dressing style draws from the aesthetics of Preppy style (Ivy League) with its college blazers, Oxford shirts, and classic loafers and the leisurely elegance of Country Club style through tailored trousers, soft knits, and chic outerwear.

It also shares connections with the British Sloane Ranger style via houndstooth prints, tweed jackets, riding boots, and the French BCBG (Bon Chic, Bon Genre) style‘s garments of discreet luxury.

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After years of managing hundreds of fashion brands from London’s office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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