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Going Broke To Look Rich: The Old Money “Aesthetic”

Old Money Aesthetic

$3000 Outfits – Old Money = No Money

In the ever-changing fashion world, the old money aesthetic is one of the more desperate and misguided. Despite this, so-called “style experts” still push it. Men chasing this old money style often try to be something they’re not, and it shows.

Especially to women. We all might want to look like George Clooney, but dressing like him won’t make it happen. If you want to buy new clothes and reboot your style, classic colors, and affordable, high-quality pieces are a good place to start. In this article, I will provide simple tips for achieving an aesthetic look. You can find your best personal style without looking like these old money guys.

If you like what you read here, check out these expert style tips:

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  5. The Proper Cloth Hopsack Jacket: A Distinct Wardrobe Advantage

Fake “Elegance”

Young model in old money fashion

Nice Clothes On A Rich (Boring) Kid

If you think the old money dressing is the peak of classic style, think again. True elegance isn’t about copying the wardrobes of the so-called aristocrats. It’s about finding a style that’s genuine, accessible, and reflects who you are. Today, those with real wealth prefer a “stealth wealth” look—high-quality fabrics and neutral colors without flaunting their riches. The average guy, like me, can be stylish without copying a particular style.  A more classic look with clothes that fit will always be fashionable for confident, interesting men.

The Myth of “Old Money”

Praised for its timelessness, old money fashion misunderstands genuine style. It’s a throwback to the 1930s elite or polished Ralph Lauren ads. While it tries to evoke nostalgia, it often misses the mark. Fashion constantly evolves, influenced by cultural, economic, and social changes. What once signified wealth can now look outdated. The “classic style” adapts over time, focusing on simple, timeless pieces that prioritize comfort and reflect your identity.

You Can’t Hide Being Broke

Adopting the old money aesthetic can be incredibly expensive. This trend suggests that to be respected or seen as successful, you must wear high-end brands and bespoke pieces. This is financially unrealistic for most and perpetuates a false narrative about success. Clothes don’t make the man; the man makes the man.

Best Summer Suits for warm weather. Collage of Cotton and Wool Blend suit with a Taupe Suit made of Tropical 130s wool

Simple. Classic. Timeless.

High-end brands linked to this aesthetic can quickly drain your finances. This strategy diverts money, requires significant personal and professional investments, and ties self-worth to material possessions. Timeless elegance and sophistication aren’t about the cost of your wardrobe. They’re found in the thoughtfulness and fit of your clothing choices.

A well-tailored blazer and a quality Oxford shirt can look better and be more affordable than trying to imitate old money fashion. On the other hand, slightly baggy clothes that taste good can be a good look.

The Ralph Lauren Mirage

Ralph Lauren and similar brands promote an idealized old money look. Too many try to imitate this style. A style of leisure and affluence is not as accessible or practical as it seems. Trying to copy this look will appear forced and uncomfortable for most guys. True elegance and style aren’t about brand names or price tags but finding clothes that fit well and suit your personal taste and lifestyle. Your clothes will not carry you in a conversation with a woman.  She is not worth your time if she is interested in you because of your expensive outfit.

Gold Digger attracted to Old Money

Old Money Style? It will BACKFIRE

Embracing Your True Style

Fashion should be an extension of your identity, not a disguise. Instead of adopting an old money aesthetic for its perceived sophistication, think about how your wardrobe can reflect your personal story and style. Fashion highlights individual strengths. Choose well-fitted clothing that flatters your physique and fits your “person.” This approach fosters confidence without relying on the appearance of inherited wealth or status symbols.

Genuine Style

Classic Style White T-Shirt and Jeans

The Easy Button – A White T-Shirt

Social media often drowns out genuine style advice with its glossy images and fleeting trends. Instead, seek inspiration from timeless style icons or consult a trusted stylist or tailor. This thoughtful approach focuses on what truly resonates with you, rather than what’s temporarily popular. By doing so, you can create a distinctive, lasting style.

Be Authentic

Embrace a timeless style that reflects who you are. Start with basics like a sharp white shirt or a well-tailored suit with leather shoes. Timeless accessories like pocket squares or a classic watch can add a personal touch. This approach emphasizes quality and fit over brand names and price tags, creating a sophisticated look that is truly yours.

Look Good. Save Money.

Twillory Blue Plaid Performance Jacket and Twillory White Performance Dress ShirtYou don’t need expensive labels to look polished. Prioritize classic pieces that offer versatility and durability. Invest in good tailoring, care for your clothes, and explore second-hand stores for unique finds. This thoughtful approach ensures your wardrobe reflects your style without straining your finances. A clean, white T-shirt always looks good when paired with jeans and a nice pair of leather or nubuck shoes. 

Conclusion: Redefining Elegance

True elegance transcends superficial wealth and outdated aesthetics. It’s about embracing authenticity and simplicity. Cultivate a wardrobe that reflects your personal journey and growth. By focusing on genuine style, you create a look that is grounded, genuine, and true to yourself. This is the future of elegance for the modern man.