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What is old money style? (Plus, how you can achieve the look)

Adopt Grandpa Core with Old Money Style

Man in newsboy hat and overcoat
Ismael Abdal Naby / Pexels

There is a new trend hitting the style industry that a surprising amount of young people are driving. While the war between Gen Z and Baby Boomers rages on in social issue and economic discussions, a bridge is being built with their clothing. Grandpa core is beginning to land with the youngest group entering the work world as they adopt pleated pants, suspenders, double-breasted jackets, and loafers. While they may rage against the elites online, Gen Z is adopting the old money aesthetic in an attempt to take it for themselves and change the narrative.

Old money style screams class, sophistication, and luxury. While trends may be full of pieces that adhere to the newest looks that go in and out of style, the old-money look sticks to classic pieces that never age out. It invests in basic pieces that may seem boring and plain but combine together to elevate every ensemble to the likes of JFK, Jay Gatsby, and countless others who defined our style in the 20th Century.

What to get for your own old money aesthetic

Man in newsboy hat and overcoat
Ismael Abdal Naby / Pexels

Recreating your own old money style is more than just borrowing your great-grandfather’s clothes. There is an art to taking what is old and making it new. At its highest example, vintage looks are refreshing and sophisticated. At their lowest attempts, they look old and unoriginal. Creating your own vintage looks while remaining new and updated is about putting a modern twist on the styles of old. Taking a new age ensemble and adding a newsboy cap to give it an old money aesthetic, or going all out with a double-breasted blazer and newsboy hat, but adding a pair of modern tailored dark wash jeans is key to creating the perfect old money style of today. Here are the individual pieces you can grab right now to transport your style back to the heyday of the 20th-century man, all while making you a 21st-century style icon.

Baker boy cap from &Sons Trading

The baker boy cap or newsboy cap is the kind of old-school upgrade that can take any ensemble and give it the rare distinction of old-world refinement. When paired with a suit and overcoat, you will bring back the days of the Peaky Blinders. When added to the modern t-shirt and jeans, you upgrade to a more elevated basic that takes a classic look and makes it trendy.

Double-breasted blazer from Southern Gents

When heading out the door, you will often look in the mirror and think of what is missing. Three out of four times, it is a blazer. We may preach a kind of elevated look that can sometimes feel overdone for the lovers of the ultra-casual, but there is something that just feels better about wearing a blazer. You can feel the eyes admiring your elegance. You notice people treating you differently, maybe even with an air of importance. You don’t have to do it for those reasons, but S. Gents’ double-breasted looks put a 2024 twist on the old-money look.

Fisherman’s cable-knit sweater from Aran Sweater Market

You may not be the kind of person who notices when a movie or TV show sets off a trend in the menswear industry, but we are. And when Chris Evans wore the cable-knit sweater in Knives Out, he created a storm of people looking for something similar. When you are putting together looks for your old-money aesthetic, the fisherman’s sweater is a must-have to really capture that 20th-century feel.

Side-buckled pleated trousers from Todd Snyder

Your regular chinos and dress pants are fine. We love a good dress pant. But if you really want to adopt the grandpa core look and give your wardrobe an aura of refined elegance, opt for something with a little more class. The sophisticated look of a pair of side-buckled trousers with pleats will take you from 2024 Manhattan to 1932 England. Wear them as Baby Boomers did with penny loafers, or add your own modern look by donning a pair of dress chelsea boots.

Where to find inspiration for your old money style

Mad Men in an office
Courtesy of AMC

Inspiration can be found all over for how to dress like a dapper mid-century gentleman. You can go with fictional men from movies and TV or real-life inspirations from politics and celebrity fame. If your grandfather or great-grandfather were masters of sartorial excellence, then you may not have to go outside of your family tree. But if you do, here is a handful of people to help inspire your new venture into old money style.

Mad Men

The drama on AMC created a buzz around mid-century society as it was for the ad men of the day. Don Draper was far from a role model in many ways, but his ability to wear his suits with pleated pants and his weekend polos is a source of divine inspiration. Remember way back in season one when he laid one of the best quotes ever on us? “You’re born alone, and you die alone, and this world just drops a bunch of rules on top of you to make you forget those facts. But I never forget. I’m living like there’s no tomorrow because there isn’t one.” Your style is yours and yours alone; wear it like you’re the only one who does.

Peaky Blinders

Thomas Shelby may not pay for his suits, but they are definitely worth more than his price. He made the subtle use of patterns like pinstripes and the fabrics like tweed their own personality. Not to mention his penchant for recreating trends (he almost single-handedly brought back the undercut). If you want to know how to wear that baker boy hat or newsboy hat, he can teach you. As if you need another excuse to binge the series again.


Ok, maybe we should add someone who is generally seen as a good man to the list. John F. Kennedy was someone who displayed the peak of style, elegance, and sophistication. He could wear a suit with the best of them, for sure, but his use of casual and preppy style, a stalwart of the old-money aesthetic, was above reproach. The nautical angle of that New Englander style is the perfect time to use that navy blazer or fisherman’s sweater.

Steve McQueen

You can’t look for mid-century style icons without bringing up Steve McQueen. He is a go-to for many angles of style that scream old money. But the most applicable pieces you can learn from him are his cardigan sweaters (perfect for pairing over those weekend polos) and his sunglasses (the perfect finishing touch on any vintage look).

There you have it, grandpa core explained. Just remember that the above inspirations are just that. Make this look your own with some of these pieces, and never forget that the goal is to emulate, not imitate. Let your personality shine through.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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