1. Owning a Cadillac
Back in the mid-20th century, rolling down the street in a shiny Cadillac was more than just transportation—it was a status symbol, according to Hylton Jorssen from GM Authority. These cars represented luxury, success, and American manufacturing at its finest. If you had a Cadillac in your driveway, people assumed you’d climbed the ladder. It was the dream car of business moguls, entertainers, and even presidents.
Cadillac’s design and performance set it apart, and owning one was seen as proof you’d arrived financially. During the 1950s and 60s especially, a Cadillac meant you weren’t just working—you were winning. It was aspirational, often appearing in movies as a symbol of wealth. Even today, older generations still see it as a gold standard.
2. Wearing a Rolex
A Rolex wasn’t just a watch—it was a wrist-bound announcement that you’d made it, according to Kimanzi Constable from Business Insider. Known for its precision and price tag, it became a favorite among CEOs, athletes, and Hollywood stars. The company leaned into the idea that success and Rolex went hand in hand. Getting your first Rolex was a major milestone, like joining an exclusive club.
The brand’s history of being associated with achievement dates back to the 1920s, when it became the first wristwatch certified as a chronometer. Later, it was worn by figures like Paul Newman and James Bond, cementing its place in pop culture. If someone flashed a Rolex, it often meant they’d reached a new level. It was as much about what it symbolized as what it actually did.
3. Having a House with a White Picket Fence
For decades, the white picket fence was the visual shorthand for the American Dream, according to Michael Dolan from Smithsonian Magazine. It meant stability, homeownership, and the ability to provide a safe, idealized life for your family. Post-World War II, as suburbs grew and GI Bill benefits kicked in, this symbol became widespread. It was a sign that you’d traded in the struggle for peace and permanence.
Owning your own piece of land was a dramatic shift from renting in the city. It meant you had a steady job, good credit, and long-term plans. The fence wasn’t just decorative—it framed your success. Even today, it’s often used in ads and films to represent an ideal life.
4. Being a Member of the Country Club
Country clubs were once the ultimate social gatekeepers. Getting accepted wasn’t just about paying dues—it meant you’d reached a certain level of respect and wealth. It offered not only golf and cocktails but a curated community of other “made it” folks. It was less about recreation and more about validation.
Through much of the 20th century, these clubs were seen as the pinnacle of suburban affluence. Some had waitlists years long, and being invited in was a major personal and professional milestone. Deals were made on golf courses, and reputations were cemented over brunches. If you belonged to a country club, you weren’t just successful—you were accepted.
5. Sending Your Kids to Private School
Private education was often seen as a privilege for the well-to-do. If you could afford to send your children to elite prep schools, it was assumed you had both means and priorities straight. These schools often came with high tuition, exclusive networks, and Ivy League pipelines. It wasn’t just about academics—it was about legacy.
In many communities, private school enrollment was a quiet way of signaling wealth. Parents saw it as an investment in generational success, according to Kasia Delgado from The I Paper. And for many, the sacrifice was worth it to maintain a certain social standing. It meant you were doing well enough to give your kids an advantage others couldn’t.
6. Flying First Class
Before airlines became more egalitarian (and crowded), flying first class was a rare luxury. It meant you’d succeeded enough to skip the lines, enjoy real food, and stretch your legs. In the 60s and 70s especially, first-class passengers were treated like royalty, complete with champagne and silverware. The experience was less about travel and more about status.
Business travelers and celebrities were often photographed boarding in style. For the average person, it was an unattainable dream, adding to its mystique. If you regularly flew first class, it showed you had not only money but importance. You weren’t just going places—you were going there in style.
7. Having a Live-In Maid or Housekeeper
Hiring full-time help was once a major benchmark of affluence. It meant your home life ran smoothly while you focused on careers or social obligations. Especially in the early-to-mid 20th century, live-in domestic workers were common among upper-middle-class families. It showed that you could afford not just a big home, but help to maintain it.
Domestic workers handled everything from childcare to cleaning and cooking. Their presence meant you had discretionary income and time. In many ways, it was a quiet symbol of having “made it” because it wasn’t just about wealth—it was about convenience and delegation. It signified a shift from survival mode to lifestyle curation.
8. Owning a Second Home
A vacation house wasn’t just about leisure—it was a visible badge of financial freedom. Whether it was a beach cottage or a cabin in the woods, a second home meant you had extra income to spend. You weren’t just working for weekends—you were investing in luxury. This was especially prominent in the boom years after WWII and again in the 1980s.
People saw these homes as retreats and future retirement nests. They also became tools for entertaining, networking, and even bragging rights. If you invited friends to your lake house, it was a subtle flex. It told the world you had enough to share—and then some.
9. Being Featured in the Local Newspaper
Before the internet, local media held real social power. If your business opening, community service, or milestone birthday made the paper, it meant you were someone of note. The local newspaper was the town’s public square, and being in it often meant respect and success. It was a tangible moment of recognition in a world before social media likes.
Weddings, graduations, promotions—these moments were validated by print. Clipping the article and framing it was common. It wasn’t fame on a national level, but it was meaningful where you lived. For many, it marked the moment their efforts were truly seen.
10. Wearing a Fur Coat
Long before fur became controversial, it was the go-to symbol of luxury and high fashion. A mink or sable coat represented sophistication and serious financial means. Often gifted on anniversaries or big milestones, it was a once-in-a-lifetime purchase. It wasn’t just about warmth—it was about prestige.
In the 1950s and 60s especially, fur coats were a staple in the wardrobes of upper-class women. Wearing one to church, the opera, or even the grocery store was a quiet proclamation of status. It meant your household income had reached a level where indulgence was allowed. Today, while fur has fallen out of fashion, its symbolism still lingers in memory.
11. Having a Personal Secretary
Before digital calendars and virtual assistants, having a human secretary meant you’d reached executive status. It signified a role so important you couldn’t manage your time or correspondence alone. This was especially true in the mid-to-late 20th century when corporate culture was booming. Your secretary was often the gatekeeper to your world.
This role wasn’t just functional—it was a marker of rank in an office hierarchy. Walking into an office where someone else took your calls and managed your day showed authority. It meant you’d moved from worker to boss. For many, this milestone symbolized a significant career leap.
12. Having a Wall of Family Portraits
This might sound simple, but elaborate, professionally done portraits signaled more than just sentimentality. They meant you had the money to commission a photographer and the home space to display them. These weren’t just snapshots—they were styled, framed, and sometimes even painted. It was a cultural cue that your family mattered and that you could afford to preserve that legacy.
From oil paintings in wealthy homes to Sears studio shoots in the suburbs, the portrait wall became a staple. It showed roots, stability, and a touch of vanity. Often displayed in foyers or living rooms, these portraits were both personal and performative. They told guests: we are proud, stable, and established.
13. Installing a Backyard Pool
A swimming pool wasn’t always standard fare—it used to be a major luxury. In the 1950s and 60s, installing one meant you had disposable income and time for leisure. Pools required maintenance, space, and insurance, so owning one wasn’t just about fun. It was about showing you could afford ongoing costs.
Having a pool also made your home a neighborhood hotspot. It turned birthdays into events and weekends into mini-vacations. Kids loved it, neighbors envied it, and real estate agents marketed it. A pool meant you’d made it to a level where fun and status could mix.
14. Owning a Color TV
When color televisions first hit the market in the 1950s, they were eye-wateringly expensive. So, having one in your living room wasn’t just about watching TV—it was about broadcasting your economic standing. By the late 60s and 70s, color TVs became more widespread, but early adopters were often seen as trendsetters. The shift from black-and-white to color mirrored a leap in lifestyle.
For many families, it was the first major tech investment. Gatherings around the TV became more immersive and exciting. If you had a color set, it was a conversation piece as much as a screen. It meant you were keeping up with the times—and doing well enough to afford to.
