10 Best Old Money Shoes in 2025
Old money style is all about timeless elegance, quality over quantity, and understated sophistication. In footwear, this means classic designs, real leather or suede materials, and impeccable craftsmanship that whispers wealth rather than shouting it.
Below, we’ve curated the ten best old money shoes from our collection — each pair capturing that heritage look without breaking the bank. You’ll find iconic loafers, boots, and more, all embodying the refined taste of generational wealth.
And importantly, we’ll show why each shoe deserves a place in a luxury wardrobe (even on a budget), with insights from fashion experts and real-world style history.
1. Old Money High Suede Loafers – Classic Slip-On Versatility
These suede loafers are a foundation of the old money aesthetic. Crafted from soft genuine cowhide suede with a sleek, low-profile silhouette, the Old Money High Suede Loafers blend comfort and elegance for everyday wear.
The design is clean and minimal, featuring durable rubber soles for flexibility.
This simplicity is exactly what makes them look “expensive” in that quiet way – there are no loud logos or gaudy hardware, just quality materials and subtle style.
Why they exude old money: Loafers have long been an “old money” favorite for their versatility. A classic penny loafer style like this effortlessly transitions from relaxed weekend attire to smart-casual business wear.
In fact, penny loafers became synonymous with Ivy League prep style as far back as the 1930s. Legend has it that college students would tuck a coin into the loafer’s front saddle slot (for payphone calls or as a good-luck token) – and thus the term “penny loafer” was born, cementing the shoe’s place in preppy tradition (the very origin of old-money fashion).
With these suede loafers, you’ll channel that heritage vibe. Try them sockless with rolled chinos in summer or paired with argyle socks and wool trousers in fall.
They’re available in a range of hues (from muted beige and fog blue to deep coffee brown), so you can opt for classic brown or black for maximum elegance, or a muted color pop (like navy or green) for weekend style.
Either way, this pair proves that understated truly means sophisticated in old-money circles.
2. Old Money Cowhide Leather Loafers – Polished Leather for a Refined Look
When it comes to looking like old money, a polished leather loafer is a must-have. The Old Money Cowhide Leather Loafers are made from genuine cow leather – you can see and feel the quality of the smooth grain.
They feature clean hand-stitched detailing and a modern low heel with contrast rubber sole. This minimalist, slip-on design can elevate casual outfits or refine a business-casual look with equal ease.
Think of these as the go-to shoes when you want to appear effortlessly put-together, whether you’re in chinos and a navy blazer or dark denim and a cardigan.
Why they exude old money: Leather loafers are “the epitome of comfort and versatility” and have been staples of wealthy wardrobes for decades.
Style guides often recommend classic penny loafers, tassel loafers, or bit loafers in black or rich brown calfskin as versatile old-money shoes that pair with everything.
This pair hits those marks with its high-quality leather and timeless silhouette. The all-day comfort (thanks to a full-grain leather insole and flexible rubber outsole) means you can wear them to the office, then straight to a dinner out – exactly the kind of unflashy luxury old-money folks appreciate.
Styling tip: Keep them shined up to a subtle gleam (nothing too patent-bright) and they’ll signal quiet luxury. Over time, the leather will develop a handsome patina.
In fact, investing in well-made leather loafers is smart for a budget-conscious gentleman aiming for a rich look – a quality pair can last years, even decades.
(Remember, cobblers can resole a good leather loafer to extend its life indefinitely. Old-money families often keep shoes in rotation for generations by maintaining them well.)
Slip these on with wool slacks and an Oxford shirt for a country club brunch, or dress down with cuffed khakis and a cashmere sweater draped over the shoulders for that elite yacht-club vibe.
3. Men’s Suede Penny Loafers – Ivy League Heritage in Soft Suede
No old money shoe list is complete without the iconic penny loafer.
Our Men’s Suede Penny Loafers take the classic design and render it in plush suede for a slightly more relaxed, but still oh-so-refined, appearance.
They feature the hallmark penny slot on the vamp (that strap across the top), a soft padded lining, and a cushioned rubber sole for comfort.
The silhouette is streamlined and dressy enough for suits, yet comfortable enough for daily wear. In Camel Brown or Chocolate suede, these loafers evoke that campus casual luxury — picture a young JFK strolling through Harvard Yard in the 1950s.
Why they exude old money: Penny loafers literally originated as an Ivy League prep staple, and they’ve remained a symbol of East Coast old-money style ever since.
Style experts note that classic penny loafers strike a perfect balance between casual and formal, making them suitable for office meetings, country club gatherings, even weddings.
The suede material here adds a “summer charm” to the loafers, which fashion writers say is ideal for warm-weather elegance. In summer, you can pair these with linen trousers or tailored shorts and a blazer, channeling a vintage Riviera vibe.
In cooler months, suede penny loafers complement grey flannel pants or cords – just add a tweed sport coat for that scholarly look.
Fun fact: The nickname “penny loafer” came from those prep school students who slid pennies into the shoe’s slot in the mid-20th century, supposedly for emergency phone call money (a payphone call cost a dime back then, but the lore stuck with pennies).
It’s a tradition that underscores how deeply these loafers are tied to old-money culture and practicality. When you wear them, you’re tapping into that heritage. And unlike ostentatious designer sneakers, these shoes quietly say “I’ve belonged here for generations.”
4. Old Money Moccasin Loafers – Casual Driving Shoes with Timeless Appeal
For off-duty days or leisurely outings, the Old Money Moccasin Loafers are the perfect choice. These loafers combine a sleek slip-on design with the classic moccasin stitching around the toe, giving them a relaxed yet sophisticated character.
They’re crafted with a breathable faux-leather upper (so they’re lightweight) and a low-profile rubber sole that’s both flexible and durable. Think of these as the weekend shoe of an old-money lifestyle: comfortable enough for running errands or driving the convertible, but stylish enough for a casual lunch at the club.
Why they exude old money: Moccasin-style loafers (often known as driving shoes or driving mocs) have been popular among the jet-set and prep set alike since at least the 1960s.
Icons like Gianni Agnelli (the Italian industrialist known for his impeccable style) sported suede driving loafers with everything from suits to denim, epitomizing laid-back luxury.
Our version captures that vibe. The signature moc-toe stitching harks back to hand-sewn Native American moccasins, which luxury brands adopted for their casual loafers – a design that old-money enthusiasts favor for its artisanal feel.
These loafers also embody the practical frugality of true old money: they’re unpretentious and built for comfort.
The rubber sole has a gentle grip (great for driving or walking on deck) and the shoe molds to your foot over time. Style them with rolled-up chinos or well-worn jeans and a tucked-in polo.
Or for a very East Coast summer look, wear pastel chinos, a thin cable-knit sweater over your shoulders, and these moccasins in a muted color (say, khaki or navy).
You’ll look like you stepped off a Nantucket sailboat. Lightweight, flexible, and classic, this pair proves that you don’t need loud designer sneakers to show you have old-money taste – sometimes a simple pair of well-made mocs says it all.
5. Luxury Suede Loafers – Bit Loafer Style with a Gold-Tone Touch
When you want a dressier loafer that still whispers class, the Luxury Suede Loafers are the answer. These shoes feature a sleek suede upper and a low-profile heel, but their standout detail is the gold-tone buckle (bit) adornment across the vamp.
That detail takes inspiration from the famous Gucci horsebit loafers – a staple of aristocratic style since the 1950s – but here it’s done in a subtle, tasteful way.
The buckle adds a refined finish suitable for weddings, cocktail hours, or dinners at the country club. Inside, you have a breathable cushioned insole, and the slip-on design makes them as convenient as they are elegant.
Why they exude old money: Bit loafers (loafers with a metal bar or buckle) are “an Old Money favorite” alongside penny loafers and tassel loafers.
They’ve been associated with European royalty and Hollywood gentlemen alike – think of photographs of the Duke of Windsor or Italian counts wearing loafers with a subtle snaffle-bit ornament.
The gold-tone hardware on our Luxury Suede Loafers signals luxury in an understated manner. It’s not a logo; it’s a piece of functional style hardware that catches the light just enough to look luxurious without screaming.
According to fashion writers, such loafers “effortlessly transition” from formal to smart-casual events. Indeed, you can pair these with a navy suit for a summer wedding (sockless loafers with a suit is a power move of the wealthy), or dress them down with tailored beige trousers and a blazer for business-casual Fridays.
The black and beige color options cover your bases – black suede with a gold bit looks great with grey flannel or a tuxedo alternative, while a light beige suede with gold bit can complement white jeans or pastel pants in spring.
As with all old-money style pieces, the key is moderation: these loafers have just enough flair to be noticed by those “in the know,” yet they remain classic in shape.
The combination of soft suede and metal bit is a nod to decades of luxury footwear tradition. Slip these on, and you instantly elevate your look to heir-apparent status.
6. Old Money Leather Oxford Shoes – The Formal Essential
Every gentleman aiming for an old-money wardrobe needs a pair of classic Oxford shoes. The Old Money Leather Oxford Shoes deliver exactly that: a distinguished, cap-toe oxford crafted from genuine cow leather in a glossy finish.
They feature a closed lacing system and a sleek, pointed toe that means business (and class).
The lining and insole are made of breathable pigskin leather for comfort – a hallmark of high-quality dress shoes. In plain terms, this is the shoe you wear with your sharpest navy suit, your tuxedo, or any time you need to exude quiet power and tradition.
Why they exude old money: Oxfords are often called “an old-money essential” for formal occasions.
They represent the pinnacle of timeless men’s footwear – think of investment bankers on Wall Street, English bankers in the City, and generations of wealthy patriarchs all sporting well-shined black or chocolate-brown Oxfords.
As the Times of India notes, an Oxford shoe in black or dark brown embodies “timeless elegance” and pairs perfectly with suits and boardroom attire.
Our Oxfords check all those boxes. They use high-grade leather that holds a shine (so keep a good polish on them), and the profile is traditional yet not outdated.
The beauty of a quality Oxford like this is its longevity. Properly cared for, these shoes can literally last decades – the leather will mold to your feet, and they can be resoled multiple times. (As a savvy style rule: replace the soles before they wear out completely, and you’ll never have to replace the shoes themselves. Many old-money families have their shoes maintained by cobblers season after season, rather than buying new pairs frequently.)
In terms of styling, a black pair is your go-to for formal events: black Oxfords with a charcoal or navy suit is as classic as it gets.
A brown pair offers a bit more versatility for day events or sport coats. For a casual spin, some aristocrats even wear dark suede Oxfords with tweed suits to country gatherings – a polished yet relaxed vibe.
Whether you’re attending a gala, a job interview, or a holiday service at an exclusive club, these Oxfords ensure you look like you belong.
7. Old Money Chelsea Boots – Sleek Boots for All-Weather Elegance
Old-money style isn’t confined to loafers and lace-ups – a pair of Chelsea boots is another footwear staple that adds a sophisticated twist.
The Old Money Chelsea Boots are ankle-high boots available in either a glossy finish or a matte beige, with that signature slim British silhouette.
They feature elastic side panels and a rear pull-tab, making them effortless to slip on and off (Chelsea boots were originally designed in the Victorian era for easy wear, after all).
With a pointed toe and a sturdy non-slip rubber sole, these boots manage to look elegant yet practical – perfect for navigating rainy city streets or country estate lawns without sacrificing style.
Why they exude old money: Chelsea boots have been beloved by everyone from English royalty to rock stars, but in an old-money wardrobe they serve as a versatile bridge between formal and casual.
A well-made Chelsea boot in black can seamlessly replace dress shoes on a damp day – pair with a tailored suit and you still look immaculate, but your feet stay dry. In fact, fashion guides highlight Chelsea boots as “an excellent option for adding a modern twist to Old Money style”, noting their comfort and ability to pair with suits as well as casual outfits.
Our Chelsea Boots embody that: the waterproof upper (in the glossy black variant) keeps you prepared for weather, and the sleek design complements both trousers and jeans.
For styling, consider the black leather Chelsea with a grey suit or slacks – it gives a slight edge while still looking classic. The glossy beige option, on the other hand, looks amazing with earth-tone chinos, cords, or even dark denim, bringing a country manor flair.
Chelsea boots also have a bit of equestrian heritage (originally made for horseback riding), which ties into aristocratic leisure activities.
Wearing these, you might feel inspired to hop into a Range Rover for a weekend in the Cotswolds – or at least you’ll look the part. Plus, Chelseas are seasonless: polished up, they work in fall/winter, and in suede or matte finishes they carry into spring.
They’re the kind of boots an old-money family’s son would wear from university lectures straight to a weekend shooting party. In short, these boots are a modern classic that rounds out your footwear rotation with a touch of rakish refinement.
8. Stitch Sole Canvas Espadrilles – Laid-Back Luxury for Summer
Old-money style isn’t all formality – when summer arrives or you’re vacationing in the Hamptons or the Riviera, you’ll want a pair of shoes that are relaxed yet still tasteful. Enter the Stitch Sole Canvas Espadrilles.
These casual slip-ons feature breathable canvas uppers with traditional jute-inspired stitching along the sole edges.
They are lightweight and easy to kick on and off, with a fabric insole that keeps your feet cool.
Essentially, they’re the perfect summer loafers: effortlessly chic and “ideal for relaxed outings and mild weather wear”.
Why they exude old money: Espadrilles have a long history in European resort towns. Think of 1950s photographs of JFK on the Amalfi coast, or Picasso in the French Riviera – often they’re in simple canvas espadrilles.
The old-money approach to casual footwear is all about embracing local classics (like espadrilles in the Mediterranean or boat shoes in New England) rather than flashy new trends. Our espadrilles combine a “casual silhouette with traditional stitched jute soles,” exactly the kind of authenticity that signals heritage style.
Fashion commentators note that such shoes ensure breathability and comfort throughout the day, which is key when you value practical quality.
Wear these with rolled linen trousers, tailored shorts, or even light seersucker pants – basically any casual warm-weather outfit gets a boost of elegance with espadrilles instead of flip-flops or sneakers.
The black or navy pair can even be matched with an unstructured summer suit for a beachfront dinner (a move the truly stylish have pulled off on Capri and Martha’s Vineyard alike). One thing to love: the stitched rope sole detail is not only aesthetic but also a nod to hand-crafted tradition.
When you choose shoes like these, you’re subtly aligning with a legacy of leisure and refinement. And unlike cheap sandals, a well-made espadrille like this will last across summers – just don’t forget to keep them dry and clean for longevity.
Slip them on for your next coastal getaway or backyard garden party, and enjoy the compliments on your “European” style savvy.
9. Montclair Loafer – Two-Tone Statement of Sophistication
For those occasions when you want your footwear to make a slightly bolder statement (while still staying in the realm of classic style), the Montclair Loafer is the answer.
This design offers a refined take on the penny loafer with a two-tone color scheme – a nod to vintage spectator shoes – blending black and white (or brown and white) for a dressier look.
The Montclair is made with a sleek PU leather upper, featuring a cushioned insole and sturdy rubber sole for comfort and durability.
Essentially, it’s a dress loafer that stands out quietly: the color contrast is sharp but the silhouette remains traditional and elegant.
Why they exude old money: Two-tone loafers (sometimes called spectator loafers or co-respondent shoes) have an interesting place in fashion history.
They were popular among the well-heeled in the 1920s and 1930s for sporting events and dances – imagine Great Gatsby-era aristocrats wearing black-and-white shoes to summer garden parties.
The Montclair captures that throwback glamour. While classic solid-color loafers are more common, a true old-money wardrobe often includes a few unique pieces with character. A gentleman might wear two-tone loafers to a celebratory event or when he’s feeling a bit daring but still wants to look proper. The key is that the two-tone is executed in a tasteful pattern (here, it’s mostly one color with accents of the other, keeping it sophisticated rather than flashy).
Our Montclair Loafer is designed “for weddings, office wear, and formal events,” adding a timeless touch to any outfit. The black-and-white version, for example, pairs beautifully with a tuxedo or a black suit and white shirt – it adds personality to formalwear.
The brown-and-white pair can complement a tan or cream suit in summer, or even dress up dark denim and a blazer for a high-low style mix. Importantly, these loafers also feature modern comfort (the cushioned insole, etc.), so unlike genuine vintage spectators, you can wear them all day without aching feet.
When you don the Montclairs, you’re embracing a bit of sartorial history.
It shows you’re confident in your style – much like old-money individuals who aren’t slaves to basic trends and can pull off something different because they know it’s rooted in classic design.
If you’re assembling a truly complete shoe collection, this pair is that cherry on top for special occasions. It’s old money meets subtle dandy flair – in the best possible way.
10. Classic Suede Slip-On Boots – Timeless Suede Ankle Boots for Smart-Casual Style
Rounding out our list is the Classic Suede Slip-On Boots, a pair of ankle boots that combine rugged appeal with tailored elegance. These boots are made of soft cow suede and designed in a Chelsea-boot silhouette (yes, elastic side gore panels and all).
They have a slightly pointed toe and a clean profile, which means they toe the line between dressy and casual. In fact, they’re described as “suitable for both smart and casual wear,” and feature a textured rubber sole for grip in cooler seasons.
Available in versatile colors like light brown, dark brown, beige, or deep green, these boots can replace your dress shoes on a crisp fall day or finish off a weekend ensemble with ease.
Why they exude old money: Suede boots, especially in a Chelsea or slip-on style, have been a favorite of style icons from the Duke of Windsor to modern royalty.
They convey a sense of country casual meets city polish. An old-money wardrobe often includes well-worn suede ankle boots for country weekends – paired with corduroy trousers and quilted jackets – as well as a cleaner pair reserved for informal dinners or outdoor events.
The Classic Suede Boots fit that heritage perfectly. They feature the elastic side panels and pull-tab that make them effortless (originating from boots made for Queen Victoria, and later adopted by the mod scene – talk about cross-class appeal!).
And with their minimalist design, they avoid any trendiness; these could easily be vintage boots from a 1970s Ralph Lauren ad, and they’ll still look just as good decades from now.
Styling suggestions: Try the dark green suede pair with grey wool slacks and a tweed blazer for a sophisticated twist. Or pull on the light brown boots with slim dark jeans and a navy sport coat for a dinner out – a combination that says you have taste but don’t need to shout about it.
Because these boots have a textured sole, they’re also practical: you won’t be caught slipping on wet pavement or grassy lawns.
It’s that blend of form and function that quietly signals an old money mentality (why have separate “dress” and “field” boots when one can do both?).
Keep the suede brushed and occasionally treat it with a suede protector spray, and these boots will age beautifully. Over time, a bit of scuff and patina on suede only adds character – something money truly can’t buy, but careful wear can achieve.
In conclusion, building an old-money shoe collection is about choosing quality classic styles that have stood the test of time. Each of the above pairs fits into that philosophy: from the all-purpose leather loafers and the Ivy League penny loafers to the durable Oxfords and the laid-back espadrilles, you have options for every occasion.
The common thread is that none of these shoes are garish or overly trendy. Instead, they rely on fine materials, proven designs, and solid craftsmanship.
As one style guide reminds us, the old-money look means paying attention to details and maintenance – keep your shoes clean and well-conditioned, and they’ll serve you for years.
In fact, investing in these classic shoes is not only a way to look the part of generational wealth, but also a smart long-term strategy (a resolable leather loafer or Goodyear-welt Oxford will outlast dozens of cheap shoes).
By picking up a selection of these “old money” shoes, you’ll be equipped for any setting with confidence.
Whether you’re dressing up for a formal event in Oxfords, enjoying a summer getaway in espadrilles, or running errands in comfy moccasins, you’ll embody that elusive mix of ease and elegance. Remember, true luxury is understated.
With the right shoes on your feet, you can step into any room and quietly let your style do the talking.
Enjoy the comfort, durability, and timeless appeal of these footwear classics – they prove that looking rich (without actually spending a fortune) is completely attainable with a bit of savvy choice. Here’s to walking your path with the confidence and grace of old money!
