In between sponsored ads for credit card debt relief programs and too-good-to-be-true claims that online surveys can help pay rent, my Instagram algorithm has recently humbled me even further through a steady stream of influencers that try and fail to imitate the iconic Old Money Aesthetic, hoping to sell me flimsy blouses that look like they came from Temu.
But there’s none of the understated elegance of fine tailoring, quality material, and muted tones that define the style. On the surface, the Old Money Aesthetic might appear plain to some, but it exudes a quiet sense of luxury. Nothing defeats old-money style sensibilities more than fast fashion pumping out polyester to fit the trend du jour. Shein and Cider sit like Scylla and Charybdis luring those who want to take part in the Gen Z-obsessed trend to their demise. If Jackie O wouldn’t touch it, neither should you.
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So, where does that leave those of us whose pockets don’t run Kennedy deep? We can shop with the old-money mindset rather than fall victim to obviously fake attempts at luxury.
Best Old Money Wardrobe Staples
- Everyday old money staple – Banana Republic Fiori Leather Belt
- The classic collar – Ralph Lauren Extended Cuff Cotton Shirt
- These business casual shorts – Steve Madden Imelda Short
- Lounge in linen – J. Crew Soleil Linen Pant
- Chunky knit crew – Traditional Aran Sweater
- Jackie O inspo – Ray-Ban Jackie OHH II Sunglasses
- Capsule wardrobe must-have – Everlane Luxe Micro-rib Turtleneck
- Best loafers – Dolce Vita Havan Loafer Mule
- Thrifted find – Prada Wool Pants
- Fall forward – Ralph Lauren Long Cashmere Dress
Everyday Old Money staple – Fiori leather belt
Three years ago, Paula from the Burlington, VT, Banana Republic gave me style advice I would carry forever. It was winter, I was nursing a breakup, it was my birthday. I walked into the store to buy a sweater dress I could crawl and hide in. Paula was in her sixties and dressed in all black, all chic. She handed me dresses from above the fitting room door. When I stepped out, I was happy—I thought my work there was done. “You’ll need to style it with a nice belt,” she told me. I did not have a nice belt. In fact, I did not own a belt at all. I told Paula this and she shook her head. “Everyone needs a nice slim belt,” she told me.
She walked away and re-emerged a few moments later with the Fiori leather belt: a black leather number with a heavy yet thin gold buckle. I put the belt on and it seemed impossible that I’d believed the look had been complete without it. Balking at the $80 price tag, I wondered if I could get an impersonator at T.J. Maxx. However, something in my soul knew Paula had my highest good in mind. I bought the belt—and not a week has gone by since when I haven’t styled it with something.
The classic collar – Ralph Lauren Extended cuff cotton shirt
Timelessness is the core essence of old money style, but quality is a close second. The Ralph Lauren extended cuff cotton shirt embodies both. The year could be 1984, 1994, or 2024, and it wouldn’t matter. This shirt works. It’s crisp and relaxed, put together and casual. Pair it with jeans and a nice slim belt, and you’re the picture of understated elegance.
Made from 100% cotton, the shirt’s magic is stored in its smallest details, like its extended barrel cuffs, point collar, shell buttons, and box-pleated back hem. Granted you don’t spill coffee down it, you will have this shirt forever.
These business casual shorts – Steve Madden Imelda short
This summer, I made it my personal mission to find a pair of shorts that were professional enough to wear to my day job as a couples counselor. Without necessarily intending it to, this quest set my compass towards the direction of old money style when I picked up the Steve Madden Imelda Shorts at a boutique in Saratoga Springs.
Made from a lightweight linen blend, these shorts sit high on the waist and the hemline falls midthigh, creating a silhouette that is loose but still tailored and polished. Its neutral ‘Field of Rye’ color and pinstripe pattern add a subtle twist to the more classically preppy khaki short. As with almost everything on this list, they style well with a pair of loafers and the Fiori belt.
Lounge in linen – J. Crew Soleil linen pant
While your trip to the Cape might require renting out an Airbnb rather than opening up the family beach house, it’s still entirely in your prerogative to lounge around in linen like you own the place. The Soleil linen pant from J. Crew is made for such an occasion. Neutral colors like White and Flax give capsule wardrobe energy, while bold red hints at old-school prep.
Chunky knit crew – Traditional Aran sweater
Chant WASP three times in the bathroom mirror — or flip through the 1980 classic The Official Preppy Handbook — and a chunky cable knit sweater might just knit itself around you.
If that doesn’t work, head over to The Irish Store for an authentic, traditional Aran sweater made from 100% merino wool. These sweaters feature a traditional honeycomb stitch and have a simple crew neck. Once again, the mark of quality is in the smallest details.
Jackie O inspo – Ray-Ban Jackie OHH II sunglasses
While the First Lady’s oversized sunglasses may have been designed by the likes of Francois Pinton, Nina Ricci, Traction, and Maison Bonnet, the rest of us can find a top-notch pair made by Ray Ban. The Jackie OHH II Sunglasses take direct inspiration from the old money style icon and are available in four different styles—including a sleek black and three different riffs on the classic tortoise shell.
Capsule wardrobe must have – Everlane Luxe micro-rib turtleneck
Getting the old money aesthetic right means building up a foundation of quality essentials that exist beyond the whims of trends. These ‘capsule’ pieces can be mixed or matched, dressed up or down, and — most importantly — kept for years to come.
Sustainability-minded Everlane makes these helpful basics, such as the Luxe Micro Rib turtleneck. Pair it with business casual shorts for a professional look, or throw it on under your crew neck cable knit on a cozy fall day.
Best loafers – Dolce Vita Havan Loafer Mule
There’s never a wrong time to wear loafers. Headed to work? Loafers. The beach? Loafers. A dinner party? You get the idea. The Dolce Vita Havan Loafers earn their keep. Whether you opt for the minimalist-minded camel suede or a more modern silver distressed leather, these loafers can pull any outfit together to make it a look.
Thrifted find – Prada wool pants
If you’re not thrifting designer online, then what are you doing? Actual rich people get rid of some pretty amazing things, and sites like Thredup exist to make sure these gems don’t end up in a landfill or long-forgotten Salvation Army basement.
The first time I thrifted a pair of Prada Pants on Thredup, I spent $97 — not much more than a pair of new pants costs at somewhere like the Gap — on a pair of pants worth over $1,000. Go snag this houndstooth pair before I do.
Fall forward – Ralph Lauren long cashmere dress
While I swear that there is no better thrift store than the Brooklyn Heights Housing Works — I once scored a similar black Ralph Lauren cashmere dress and Purple Label black bodysuit for about $100 total — The Real Real is a treasure trove of online thrifting that’s dedicated specifically to luxury fashion. This Ralph Lauren cashmere shift dress is perfect for carrying old money fashion into fall.
