How to Dress Old Money: A Comprehensive Guide to Timeless Elegance

When it comes to style, “old money” fashion represents a sophisticated, understated aesthetic that has withstood the test of time. This style isn’t just about expensive clothes; it embodies a lifestyle marked by tradition, class, and an appreciation for quality over flashiness. In this article, we’ll explore how to dress in an “old money” style, from wardrobe essentials to grooming tips, all while embracing a mindset that transcends trends.

Understanding Old Money Style

Before we delve into the specifics of dressing “old money,” it’s crucial to understand what this term means. Old money refers to families or individuals who have been wealthy for several generations. Their style often reflects a certain restraint and understated elegance that shuns ostentation in favor of classic, timeless pieces.

Old money style is characterized by:

  • Quality over Quantity: Investing in fewer, high-quality pieces instead of a vast wardrobe filled with trendy items.
  • Subdued Colors and Patterns: Earthy tones, pastels, and classic patterns like houndstooth, plaid, or pinstripes dominate the old money palette.
  • Tailored Fit: Garments should fit impeccably, emphasizing the wearer’s shape without being overly tight or loose.
  • Classic Accessories: Jewelry and accessories are often understated, including pearls, leather belts, and elegant watches.

Wardrobe Essentials for Old Money Style

Building an old money wardrobe starts with key pieces that embody timeless style and quality. Here’s a breakdown of the essentials you’ll want to include in your closet.

1. Tailored Suits

A well-fitted suit is the cornerstone of old money style for both men and women. Look for classic cuts in neutral colors like navy, charcoal, or beige.

  • Fabric: Opt for high-quality materials such as wool, cashmere, or tweed. These fabrics not only look sophisticated but also last for years.
  • Fit: Make sure the suit is tailored to your body. A skilled tailor can make all the difference, ensuring that your suit enhances your silhouette.

2. Classic Dresses and Skirts

For women, classic dresses and skirts are vital components of an old money wardrobe.

  • Styles: A-line dresses, shift dresses, and pencil skirts are timeless choices. Look for pieces that cinch at the waist and fall just below the knee.
  • Colors: Stick to muted colors and classic patterns like stripes or florals that are not overly loud or attention-seeking.

3. Crisp White Shirts

A collection of well-made, crisp white shirts is essential for both men and women. These can be paired with almost anything and instantly elevate an outfit.

  • Material: Choose high-quality cotton or linen for breathability and comfort.
  • Fit: Look for a tailored fit that complements your body shape. For women, a button-down or fitted blouse works wonders.

4. Cashmere Sweaters

Cashmere sweaters are a luxurious addition to your wardrobe, perfect for layering or wearing alone.

  • Styles: Opt for crew necks or V-necks in neutral tones like gray, beige, or navy.
  • Care: Cashmere requires gentle care, so always hand wash or use a delicate cycle when cleaning.

5. Chinos and Tailored Trousers

Chinos or tailored trousers are versatile pieces that can be dressed up or down.

  • Colors: Stick to earthy tones like khaki, olive, or navy.
  • Fit: Make sure they’re tailored to your body, falling neatly at your ankles without excessive bunching.

6. Footwear

Old money style often emphasizes quality footwear that is both stylish and comfortable.

  • Men’s Shoes: Invest in leather loafers, brogues, or oxfords in classic colors like black or brown.
  • Women’s Shoes: Classic pumps, ballet flats, or ankle boots in leather or suede work well.

7. Outerwear

Investing in quality outerwear is essential for an old money wardrobe.

  • Coats: Look for tailored trench coats or wool overcoats in classic colors.
  • Jackets: A tailored blazer can elevate any outfit, whether it’s paired with trousers or a skirt.

Accessories: The Finishing Touches

Accessories play a pivotal role in defining old money style. The key is to choose items that enhance your look without overwhelming it.

1. Scarves

A luxurious cashmere or silk scarf can add a touch of elegance to your outfit.

  • Colors: Choose scarves in classic patterns like houndstooth or simple stripes.
  • Draping: Wear them casually draped around your neck or tied elegantly for a polished look.

2. Handbags

Quality handbags should be functional and stylish.

  • Materials: Opt for leather or suede in neutral colors. Brands like Hermès or Gucci are classic choices, but prioritize quality over brand names.
  • Styles: A structured tote or a classic clutch can elevate any outfit.

3. Jewelry

Old money style leans towards understated elegance in jewelry.

  • Materials: Gold or silver in simple designs works best. Pearls are a classic choice for women.
  • Styles: Avoid flashy pieces; instead, choose timeless designs that complement your outfit.

4. Watches

A classic watch adds sophistication and practicality.

  • Design: Look for leather straps and simple dials. Brands like Rolex or Patek Philippe represent timeless craftsmanship without being overly ostentatious.

Grooming and Personal Care

Dressing in old money style isn’t just about clothing; personal grooming plays a significant role as well.

1. Hair

Maintain a clean, polished hairstyle that reflects understated elegance.

  • Men: A classic haircut that is neat and well-groomed works best. Avoid overly trendy styles.
  • Women: Consider a simple yet elegant hairstyle, like a low bun or soft waves.

2. Skin Care

Healthy skin is the foundation of looking polished.

  • Routine: Invest in a good skincare routine that includes cleansing, moisturizing, and sun protection.
  • Makeup: For women, opt for natural makeup that enhances your features without being too heavy or dramatic.

3. Fragrance

Choose a subtle, classic fragrance that reflects your personality without overwhelming those around you.

  • Notes: Opt for light floral or woody scents that provide a refreshing touch without being overpowering.

Building an Old Money Wardrobe on a Budget

Dressing in old money style doesn’t have to break the bank. Here are some tips for building your wardrobe without overspending.

1. Thrifting and Vintage Shops

Explore thrift stores and vintage shops for hidden gems. Many classic pieces can be found at a fraction of the retail price.

  • Quality Check: Always inspect the fabric and condition before buying.
  • Alterations: A tailor can help you customize any piece to achieve the perfect fit.

2. Capsule Wardrobe

Consider creating a capsule wardrobe, which consists of versatile pieces that can be mixed and matched.

  • Key Pieces: Invest in timeless staples that can be worn in various combinations.
  • Seasonal Changes: Update your capsule wardrobe with a few seasonal pieces each year to keep it fresh.

3. Quality over Quantity

Focus on investing in a few high-quality pieces rather than a large number of trendy items.

  • Research: Learn about brands known for their craftsmanship and sustainability.
  • Sales: Keep an eye out for sales or outlet stores where you can find quality items at reduced prices.

Dressing for Various Occasions

Understanding how to adapt your old money style for different occasions is essential. Here are some tips for various settings.

1. Casual Settings

Even in casual settings, maintaining an air of sophistication is key.

  • Outfit Ideas: Pair a cashmere sweater with tailored chinos or a classic pair of jeans. Complete the look with loafers or elegant flats.
  • Accessories: Keep accessories minimal, perhaps with a classic watch and a simple scarf.

2. Business Attire

For professional settings, ensure your outfit conveys authority and confidence.

  • Men’s Attire: Opt for a tailored suit in a neutral color, paired with a crisp white shirt and leather shoes.
  • Women’s Attire: A tailored blazer over a fitted dress or blouse and skirt combination is both professional and chic.

3. Formal Events

Formal occasions demand an elevated approach to your old money style.

  • Men’s Attire: Consider a tuxedo or dark suit with a silk tie. A classic watch adds a refined touch.
  • Women’s Attire: A floor-length gown or a sophisticated cocktail dress paired with elegant heels and understated jewelry is ideal.

Cultural Considerations in Old Money Fashion

Understanding the cultural context of old money fashion is vital for embodying this style authentically.

1. Global Influences

Old money style varies across cultures. For example, British old money might emphasize tailored tweed jackets and wellington boots, while American old money may lean towards preppy styles like polo shirts and loafers.

2. Tradition and Heritage

Respecting tradition is a key component of old money style. Many families pass down heirloom pieces, whether it’s a classic watch or a vintage handbag.

  • Incorporating Heirlooms: Wearing family heirlooms not only adds character to your outfit but also connects you to your history.

3. Social Etiquette

Old money isn’t just about what you wear; it’s about how you carry yourself. Good manners, humility, and a genuine attitude are just as important as your wardrobe.

Conclusion

Dressing in an old money style is not merely about fashion; it reflects a way of life steeped in tradition, quality, and understated elegance. By focusing on timeless pieces, high-quality fabrics, and a polished appearance, you can embody the essence of old money. Remember, it’s not about how much you spend but about the style, craftsmanship, and sophistication you choose to embrace.

Embrace the old money aesthetic by investing in your wardrobe wisely, prioritizing fit and quality, and adopting a lifestyle that values tradition over trends. With these tips and insights, you’ll be well on your way to mastering the art of old money style.