The art of looking wealthy without effort: the holy grail of the Old Money aesthetic.
The 5 core competencies of old money are as following:
Timelessness, Understatement, Heritage, Quality & Discretion.
To embody this image, you must let go of any desire to follow fleeting fashion trends. Your wardrobe should be a capsule of timeless pieces that carry you season to season, year after year. This style isn’t about showmanship. It’s about the implication of status, one you have been born with. As if you come from a long legacy of wealth, perhaps you are even a legacy at an Ivy League.
Popularized by Ralph Lauren in the 1960s, the American interpretation of British prep exploded in popularity on and off the runway. Lauren’s use of tweeds, oxfords, penny loafers and tortoiseshell glasses evoked a bookish look—a kind of intellectualism that hadn’t been coveted before.
Tom Ford (during his time at Gucci), Coco Chanel and The Row showcase the range within this style: trench coats, cable-knit sweaters, high heels and scarves wrapped in quintessential Jackie O fashion; polos, khakis and blazers — all coming together with subtle power that convey the inner confidence we usually associate with those who embody this look, or indeed have their roots in generations of wealth.
The perfectly worn-in sweater that hints it could have been passed down, or inherited. Suedes and leathers that have gracefully aged in the sun, the effortless cashmere tied in a knot and draped over one’s shoulders. Each of these elements reflects a zen detachment from fleeting trends, embodying a practical elegance that only grows richer with time, like the patina of heirloom silver. The pieces operate in a highly functional way, all having impressive lifespans that keep them looking timeless over the years. The Old Money wardrobe is not disposable. This is key. As we’ve said before, Old Money is the master of implication. The exclusivity lies in the knowledge itself, a silent symbol that if you know, you know.
Jacqueline Kennedy Onassis is the epitome of this aesthetic.



The elegance through minimalism she exuded is highly coveted and replicated all over the world, proof that can be found in the Pillbox hats and sheath dresses worn today. From her tailored suits, pearls, and signature oversized sunnies, she is the favorite child of polish and refinement. Even at her most casual, she appeared to be effortlessly chic; her confidence was warmly felt and her style pulled people towards her like a magnet.
In summary, lets circle back to the core competencies we discussed in the beginning:
Timelessness: Invest in pieces meant to last a lifetime, transcendent of trends.
Understatement: Avoid logos and ostentatious displays at all costs. Money talks, wealth whispers.
Heritage: Shop for classic brands and heirloom pieces that echo tradition. Take care that your pieces will last the test of time through their classic stylization.
Quality: Prioritize craftsmanship, tailoring and textiles. Buy used, thrifted, whatever you like; simply take it to a tailor to have it fit to your body.
Discretion: Keep your elegance quiet, subtle. The less attention you demand, the more your legacy will be cemented.
A final request: always maintain your composure, slip on your loafers and grab your boat keys. Tonight, we toast to the luxury of being effortlessly unseen.
With great personal aesthetic,
Alexandra Diana, The A List
LOVE!