9 Essential Tips on How to Dress Like Old Money: Timeless Elegance and Subtle Luxury for a Classic Wardrobe!

Wondering how to dress like old money? Our guide helps you master the look with classic, high-quality pieces that embody timeless elegance and understated luxury.

Dressing like old money is like entering a world where quality trumps quantity and style is timeless. You don't need an inheritance to achieve this look, it's all about making smart, refined choices. Opt for neutral colors, high-quality fabrics, and minimalist accessories. Select timeless pieces like blazers and tailored items, and don't underestimate the power of good grooming.

But where do you start? What are the must-have items and where can you find them? Stay tuned to unlock the secrets behind the old money aesthetic.

This post is all about how to dress like old money.

How To Dress Like Old Money

1. Understanding the Old Money Aesthetic

If you've ever been captivated by the timeless elegance of figures like Jackie-O or Paul Newman, you're already familiar with the Old Money Aesthetic, a style that draws its inspiration from generational wealth, classic style icons, and powerful family dynasties such as the Kennedys and Vanderbilts. This aesthetic is all about quality, designer pieces without flashy logos, precise tailoring, and a nod to classic American prep. It's a sophisticated elegance that never goes out of style.

The Old Money Aesthetic is a testament to the adage that less is more. It's not about flashy trends, but rather, about timeless colors like black and navy, and fabrics that speak of quality like cashmere and silk. It's about a sense of understated elegance, reflecting generational wealth without explicitly flaunting it. This aesthetic is embraced by celebrities such as Gwyneth Paltrow and Blake Lively, who symbolize its unassuming sophistication.

The Old Money Aesthetic isn't just about looking rich; it's about embodying a certain level of class, a refined style that's always in vogue. It's about understanding the value of quality over quantity, of timeless elegance over passing trends.

2. Essential Old Money Pieces

Now that you have a firm understanding of the Old Money Aesthetic, let's explore some of the essential pieces that embody this timeless look. Your wardrobe isn't complete without a high-quality white linen dress. Perfect for summer soirees, it effortlessly blends elegance with casual chic.

Next, consider lightweight wool blazers. A staple in any sophisticated wardrobe, they help achieve that understated, yet polished look that's synonymous with old money. Paired with loafers or classic pumps, you've got an ensemble that screams wealth without being flashy.

Now, let's discuss accessories. Classic straw hats are more than just sun protection; they add a touch of sophistication to any outfit. They're the perfect complement to a white linen dress, elevating your look from casual to elegant.

Your footwear is just as important. Wedge espadrilles are a must-have for a timeless look. They're casual, yet classy - perfect for a garden party or yacht trip. And don't forget loafers and classic pumps. These essential pieces are versatile, comfortable, and always in style. Remember, the key to the old money look is investing in high-quality, timeless pieces that can be worn season after season.

3. The Art of Accessorizing

Mastering the art of accessorizing is key to truly capturing the old money aesthetic, with every piece chosen for its understated elegance and timeless design. Your accessories should subtly whisper sophistication, not shout for attention.

Pearls are a perfect choice; their understated elegance makes them a classic accessory. Opt for a simple pearl necklace or a pearl-encrusted pin that adds a touch of refinement to your outfit. Leather, another high-quality material, can be incorporated through a well-crafted belt. This not only structures your outfit but adds a layer of sophistication.

A silk scarf is another must-have. It's a flexible accessory that can be draped around your neck, tied to your bag, or used as a headband. These details add a certain charm to your ensemble.

Don't forget the classic watch. It's more than a timepiece; it's a statement of taste and class. Choose one with a sleek, minimalistic design to keep up with the old money aesthetic.

4. Old Money Outfits for Men

When it comes to embodying the old money style for men, emphasis is placed on loose-fitting, tailored items that exude a classic and sophisticated vibe. The key isn't about flaunting wealth, but rather showcasing a timeless elegance.

Investing in quality pieces is crucial to achieving the old money flair. Brands like Tommy Hilfiger and Lacoste offer a range of clothing that aligns with this aesthetic. Their pieces aren't only high-quality but also feature classic designs, making them staples in an old money wardrobe.

Leather accessories, such as sturdy belts and polished shoes, are must-haves. They further enhance the sophisticated style while adding a touch of luxury. And don't forget about sunglasses. A pair of classic wayfarers can instantly elevate your look, giving off a vintage vibe that's inherent to the old money aesthetic.

Looking for inspiration? Celebrities like Shawn Mendes and Jude Law have mastered the old money style. Their fashion choices are a testament to the power of well-constructed, tailored items and a classic aesthetic. Remember, it's not about trends, but about a timeless style that signifies wealth without being ostentatious.

5. Old Money Outfits for Women

Just as men have their own unique approach to the old money aesthetic, women too can embrace this timeless style, taking cues from fashion-savvy celebrities like Sophia Richie and Victoria Beckham. For Old Money outfit ideas, consider pairing a boyfriend blazer with riding boots for a classic, understated elegance.

Another key to mastering this aesthetic is investing in quality over quantity. Focus on classic pieces that offer versatility and longevity. A crisp white blouse, for instance, exudes timeless elegance, especially when paired with a trench coat. The combination is a testament to the Old Money principle of timeless styles.

Neutral colors are another staple of this aesthetic. Think beige, navy, cream, and black. These hues create a sophisticated palette that transcends seasons and trends.

Incorporating retro prints like stripes, polka dots, and houndstooth also adds an old-school charm to your Old Money look.

Last, but not least, timeless accessories can make or break your outfit. Look for pieces that exude understated elegance, like a simple pearl necklace or a classic leather handbag. These add the finishing touches to your outfit, further emphasizing the Old Money ethos of quality over quantity.

6. Special Occasions: Old Money Dressing

Dressing for special occasions calls for a different level of attention to detail. For men, this means opting for impeccably tailored suits or tuxedos. Your tuxedo or dark suit should be a testament to your sophistication and display the artistry of impeccable tailoring. Pair it with a crisp white dress shirt with French cuffs, tasteful cufflinks, a silk bow tie or necktie, and a pocket square to further elevate your look.

Women, on the other hand, should choose elegant evening gowns or cocktail dresses in rich fabrics. These choices should reflect a timeless elegance synonymous with the old money aesthetic. Color palettes should lean towards classic hues that exude a sense of understated luxury. Complete your ensemble with tasteful heels, elegant jewelry, and a chic clutch for that extra touch of class.

7. Navigating Brands and Shopping

To achieve the classic old money look, you'll need to navigate a myriad of brands known for their timeless style and superior quality. These brands, such as Ralph Lauren, Hermès, and Brooks Brothers, offer the key wardrobe staples that define the old money aesthetic.

Shopping for these items can be an art in itself. Here are four strategies to help you find the right pieces:

1.         Check out upscale department stores like Bloomingdale's, Nordstrom, and Saks Fifth Avenue. They often curate collections that align with the old money style.

2.         Dive into heritage brands such as Burberry, Gucci, and Chanel. These brands have a long history of creating classic and sophisticated pieces.

3.         Don't overlook online retailers. Platforms like Net-a-Porter, Matches Fashion, and Mr. Porter offer a wide selection of high-end fashion.

4.         Invest in key wardrobe staples. Renowned designers like Tory Burch and Michael Kors design pieces that blend seamlessly into an old money wardrobe.

8. Old Money Hairstyles Guide

Stepping into the world of Old Money hairstyles, you'll find that classic cuts, well-groomed facial hair for men, and elegant updos or timeless chignons for women are the hallmark of this refined and understated aesthetic. For you, as a man, a clean-cut side parting or slicked-back hair speaks volumes about your personal style, exuding an air of sophistication and subtle power. Keeping your facial hair well-groomed is essential to complete this polished look.

In contrast, women have a plethora of options from free-flowing waves to elegant updos and timeless chignons. These classic hairstyles aren't only effortlessly chic but also serve as an epitome of understated elegance. The addition of sophisticated hair accessories such as pearl-encrusted pins or refined hairbands can further elevate your hairstyle, adding a touch of Old Money charm to your overall ensemble.

Regardless of your gender, remember, your hair choice should reflect your personal style, embodying the understated elegance that's synonymous with the Old Money aesthetic. It's about achieving a perfect balance between refinement and modesty, where less is indeed more.

9. Beyond Wardrobe: The Old Money Mindset

Embracing the Old Money mindset goes beyond simply dressing the part; it's about valuing quality over quantity in all aspects of your life. It's about incorporating timeless elegance and sophistication into your daily routines and interactions. This mindset isn't just about appearances, it's about embodying a set of values and principles.

To truly embrace this, consider these four key points:

1.         Prioritize education, etiquette, and refined social skills. The old money class places a high value on cultural refinement and knowledge.

2.         Invest in experiences and personal growth rather than material possessions. This shows a preference for quality over quantity.

3.         Uphold traditions and family heritage. This emphasizes the importance of generational wealth and the preservation thereof.

4.         Embody timeless elegance and sophistication. This isn't just about dress but also behaviour, communication, and overall demeanor.

This post was all about how to dress like old money.