Welcome to the realm of the “old money” aesthetic outfits – a realm where quality trumps quantity and tradition holds court.
Step into a world of timeless elegance, where sophistication is a lifestyle and style is inherited, not purchased.
You see, this isn’t just about clothes. This is about embodying an entire ethos of understated opulence, refinement, and good taste.
Buckle up, gentlemen, because we’re about to take you on a sartorial journey through the 15 quintessential ‘old money’ outfits that will make you look like you’ve just stepped off a yacht in the Hamptons.
Ready? Let’s dive in!
Table of Contents
Boardroom Boss
You’re at the head of the table, a charcoal gray pinstripe blazer commanding respect.
A crisp white shirt and silk tie speak volumes about your taste. A classy pair of black dress pants complement the getup.
While black leather brogues ground us in tradition.
Metropolitan Magnate
Imagine yourself in a bustling cityscape, figures defined by a sharp, charcoal-grey suit.
A crisp white shirt peeks out from beneath, paired with a tasteful patterned blue silk tie that whispers, not shouts, about your presence.
Polished brown derbies adorn your feet, giving a grounded, commanding air.
With this outfit, you’re not just attending important business meetings but commanding them.
Renaissance of the Roaring Twenties
You’re breathing in the sun at a summer garden party in a white linen suit.
The pastel-colored shirt adds a splash of color, or you can be more conservative and don a tan t-shirt.
Brown sneakers anchor it to the earth beautifully.
A Panama hat shades your eyes, throwing you back to an era of undeniable charm. You’re a vintage icon, reborn.
Coastal Chic Casual
Picture us strolling along the beachfront as the sun sets.
You’re in a breezy, beige linen button-up shirt, casually rolled up at the sleeves, paired with white chino pants.
A woven leather belt secures our relaxed yet refined look. On our feet, comfortable black leather sandals let us feel the cool sand.
You’ve traded in the suit for the sea – and looking stylish as ever.
The Ivy League Intellectual
While striding through grand university halls, a blue-striped polo shirt is impeccably tailored.
A navy sweater beautifully complements the shirt and speaks of deep thoughts and scholarly pursuits.
Brown leather oxfords click on the stone floors, and a classic leather briefcase carries an intellectual arsenal.
You’re not just educated – you’re a sartorial scholar.
City Stroll Sophisticate
Our tailored camel overcoat radiates urban elegance when making our way through a bustling city.
Underneath, a navy suit, a white shirt, and a red tie create a refined contrast.
Brown leather oxfords echo the city streets. In the city that never sleeps, neither does our style.
Vineyard Vignette
Surrounded by lush vineyards, raising a toast to style.
You’re in a pristine white dress shirt, the epitome of timeless elegance, tucked into smart cream shorts that capture the warmth of the summer sun.
On your head, a classic Panama hat provides shade and an extra dash of sophistication.
Blue loafers on your feet add a pop of color, mirroring the clear sky above.
You’re not just tasting the wine but basking in the rich bouquet of old money fashion.
Countryside Connoisseur
Picture yourself taking a leisurely stroll in the English countryside on a brisk autumn day.
Enveloped in the rich textures of a brown tweed sport coat, its earthy tones echoing the autumnal hues around us.
Underneath, a brown turtleneck adds a layer of cozy sophistication.
At the same time, the navy dress pants ground the outfit and add a hint of contrast.
Read more: turtleneck with blazer.
You can also accessorize your look with a metal pin that matches your brown outfit.
If you want a more perfect effect, you can make your own custom metal pins at Pins.Us.
A small, dainty metal pin can also add charm to your outfit.
Finally, brown suede loafers stride comfortably over the cobblestone paths, marrying rustic charm with refined elegance.
Maritime Elegance
Imagine standing on the deck of a yacht, the sea breeze rustling your navy blazer with gold buttons.
A crisp white Oxford shirt adds a breath of fresh air when paired with your sophisticated white dress pants.
Additionally, brown loafer shoes echo the deck beneath. You’re the captain of the sea – and of style.
Yacht Club
Basking in the sun-dappled decks of a yacht club. While effortlessly cool in a navy sweater, its color reflects the summer skies.
You’ve traded in chinos for tailored white shorts, capturing the spirit of casual elegance.
On your feet sporting a pair of loafers or boat shoes, perfectly at home on the deck.
Polo Club Chic
Picture this, stepping onto a lush polo field bathed in sunlight.
While donning a crisp white button-down tucked into tailored beige chinos, topped with a navy blue v-neck cashmere sweater draped casually over your shoulders.
Tan loafers cushion your feet, keeping them comfortable and chic. This outfit says, “You’ve arrived,” but in a subtly elegant way.
Autumnal Aristocrat
You’re wandering through falling leaves, clad in a brown suit and a turtleneck sweater in a rich autumnal hue.
The brown Oxford dress shoes crunch leaves beneath.
A wool scarf completes the warm, layered look. As the seasons change, so do you.
The Vintage Voyager
You’re exploring the open road, clad in a brown leather bomber jacket.
Underneath, an olive roll-neck sweater offers warmth, while gray dress pants complement the adventurous spirit.
Brown leather Chelsea boots tread on uncharted territory and are ready to voyage into the wild – all while keeping our style game strong.
Country Club Casual
At the club, leisurely enjoying the day in a light orange polo t-shirt and light gray shorts.
White sneakers are a nod to casual comfort, while a white leather belt weaves a narrative of relaxed refinement.
You’re playing the game of golf with style – and winning.
Weekend in the Hamptons
You’re lounging on a sun-drenched terrace, sporting a white button-down shirt and pink shorts.
The white leather loafers whisper of luxurious leisure, inviting casual conversation and carefree days.
Here in the Hamptons, it’s all about casual elegance.
Things to Consider when Dressing the Old Money Aesthetic Look
Before we bid you farewell, we want to leave you with a few golden nuggets of wisdom.
Keep these points in mind, and the old money aesthetic will be yours to command!
Quality Over Quantity
You see, less is more in the world of old money style. It’s not about owning a closet full of clothes; it’s about carefully curated pieces that stand the test of time.
Each item should be a testament to excellent craftsmanship and enduring style.
Forget fast fashion; you should be investing in the classics that will still look stylish in a decade – or even two.
Neutral Colors
When dressing old money, embrace a palette of neutrals.
Think shades of navy, gray, beige, white, and black. Muted colors not only exude a sense of timeless elegance but also give us the flexibility to mix and match with ease.
Remember, we’re not aiming for flashy but an effortlessly sophisticated look.
Brands That Scream Old Money Style
Look for brands with a rich heritage and a proven track record of quality.
With their iconic suits and Oxford shirts, Brooks Brothers have been a staple in the old money wardrobe for the wealthy man. For generations.
Ralph Lauren, known for their classic Polo shirts and preppy vibe, is another go-to choice.
Other brands like Barbour, Burberry, and J.Press encapsulate this timeless aesthetic.
By investing in these brands, you’re not just buying clothes; but buying into a tradition of elegance.
It’s Obvious, But a Proper Fit is a MUST
We cannot stress this enough – the fit is EVERYTHING.
No matter how expensive or high-quality your clothes are, the entire look falls flat if they don’t fit well.
So, let’s commit to those extra steps to ensure our clothes fit just right, whether finding a reliable tailor or spending a little more time in the fitting room.
Remember, when it comes to old money style, you’re dressing to impress, not just to cover up.
