How to Dress Like Old Money: Winter Outfits, Aesthetic, and Clothing Brands

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Introduction

The “Old Money” style is all about timeless elegance, subtlety, and sophistication. Unlike trends that come and go, the old money aesthetic exudes a refined, understated look that speaks volumes about heritage and wealth without the need for flashy logos or exaggerated designs. It’s an aesthetic that doesn’t chase trends but rather stays rooted in classic and high-quality garments. In this article, we’ll dive into what exactly defines the old money style and how you can embody this look, especially during the winter season.

What is the Old Money Aesthetic?

The old money aesthetic is grounded in a sense of tradition, often tied to wealthy families who have passed down wealth and style through generations. It’s a look that prioritizes discretion, quality, and durability, with a focus on well-made, timeless pieces.

In contrast to the “new money” style, which can be characterized by ostentation and brand-driven fashion, old money style is about investing in clothing that lasts both in terms of durability and fashion ability. Key features include:

  • High-quality materials like cashmere, wool, silk, and tweed
  • Neutral colour palettes with shades of beige, navy, grey, and forest green
  • Tailored, fitted clothing that is neither too tight nor too loose
  • Understated elegance without logos or flashy designs

Old Money Style in Winter: Key Principles

Winter fashion in the old money aesthetic sticks to the same principles of subtlety and timelessness but with an emphasis on practicality. The focus is on layering, warmth, and enduring fabrics like wool, cashmere, and leather. Here are some key principles for winter dressing:

  • Choose classic, long-lasting pieces over trendy items.
  • Prioritize fabrics like wool, tweed, and cashmere for warmth and elegance.
  • Stick to neutral tones like black, grey, camel, and navy for a sophisticated winter look.

Old Money Winter Outfits for Men

For men, winter is the perfect season to layer up in luxurious fabrics while keeping a polished, refined look. Key winter items include:

  • Outerwear Essentials: opt for wool coats, double-breasted trench coats, or peacoats in neutral shades like navy, grey, or camel. A classic camel-colored overcoat is a quintessential old money piece.
  • Layering: Pair cashmere or wool sweaters with button-down shirts for a refined but cozy look. Vests can also add a touch of sophistication when layered under a coat.
  • Trousers: Go for wool or flannel trousers that offer warmth without compromising on elegance.
  • Footwear: A polished pair of leather loafers or Oxford shoes elevates any winter outfit. For more casual looks, Chelsea boots or brogues work well.

Old Money Winter Outfits for Women

Women’s old money winter outfits are all about blending luxury with practicality. Think refined silhouettes and classic layering pieces:

  • Coats: A long wool or cashmere coat in camel or navy is an essential. Belted trench coats or capes also work for an elegant, old-school winter look.
  • Knitwear: Opt for cashmere turtlenecks, cardigans, or sweaters, all of which can be effortlessly layered over blouses or dresses.
  • Bottoms: Tailored trousers or tweed skirts offer warmth while maintaining a sharp, sophisticated silhouette.
  • Footwear: Choose from leather riding boots, classic loafers, or understated pumps for a timeless winter look.

Old Money Aesthetic for Men: Key Elements

Dressing with an old money aesthetic involves careful attention to fit and quality. For men, the style can be defined by the following:

  • Tailoring: A well-fitted blazer, suit, or sport coat made from wool or tweed should be the cornerstone of the wardrobe.
  • Materials: Cashmere sweaters, cotton button-downs, and wool trousers all add to the luxurious feel.
  • Accessories: Understated, elegant accessories like leather gloves, scarves, and watches add the finishing touches to the old money look.

Old Money Aesthetic for Women: Key Elements

For women, the old money aesthetic is defined by quiet luxury and timeless elegance:

  • Simplicity: Avoiding overtly trendy or flashy styles, sticking to classic cuts and understated designs.
  • Signature Fabrics: Tweed, cashmere, and silk are go-to materials, lending a luxurious feel to the simplest of outfits.
  • Jewellery: Pearls and delicate gold pieces are ideal for embodying the old money aesthetic. Subtle diamond studs or a fine bracelet complete the look.

How to Dress Like Old Money: General Guidelines

Want to adopt the old money look? Here are some tips to get you started:

  • Quality over Quantity: Invest in high-quality, durable pieces that will last.
  • Tailoring is Key: Make sure your clothes fit well and avoid overly loose or too-tight garments.
  • Keep it Neutral: Neutral color palettes are a hallmark of old money style—think beige, navy, grey, and white.

How to Dress Like Old Money for Women: Specific Tips

Women aiming for the old money look should focus on timeless elegance and minimalism. Here’s how:

  • Choose Luxurious Fabrics: Cashmere sweaters, silk blouses, and wool trousers are must-haves.
  • Accessorize Sparingly: A silk scarf or a structured handbag can add just the right touch of sophistication.
  • Keep Hair and Makeup Polished: The old money woman embraces natural beauty, opting for a sleek hairstyle and minimal makeup.

How to Dress Like Old Money for Men: Specific Tips

Men can channel the old money aesthetic by paying attention to the following:

  • Stick to Tailored Classics: A well-fitted wool coat or blazer is a wardrobe essential.
  • Embrace Traditional Colors: Navy, grey, and beige are timeless options for outerwear and suits.
  • Elevate with Accessories: A quality leather belt, cufflinks, or a watch can make all the difference.

Iconic Old Money Clothing Brands

Certain brands are synonymous with the old money aesthetic due to their long-standing reputation for quality and timeless design. Some of the most iconic include:

Ralph Lauren: Known for its preppy, country club style.

Brooks Brothers: A favorite for classic suits and formalwear.

Hermes: Renowned for its luxury leather goods.

Burberry: Famous for its trench coats and traditional British style.

Zegna, Loro Piana, and Max Mara etc.

Old Money Outerwear Essentials for Winter

A great coat is an investment piece that will last for years. Wool overcoats, trench coats, and peacoats are perfect for winter and fit seamlessly into the old money style. 

Footwear Choices in the Old Money Aesthetic

Footwear is just as important as clothing when creating a refined look:

  • For Men: Stick to polished Oxfords, loafers, or brogues in brown or black leather.
  • For Women: Leather riding boots or classic pumps in understated designs are ideal.

 

Common Mistakes to Avoid When Trying to Dress Like Old Money

It’s easy to miss the mark with the old money aesthetic if you:

  • Overdo logos: Avoid garments with loud logos or branding.
  • Chase trends: Stick to timeless classics instead of trendy fashion.
  • Ignore the fit: Always ensure your clothes are well-tailored for a polished look.

Conclusion

Embracing the old money aesthetic isn’t about chasing trends or flaunting wealth—it’s about mastering the art of understated luxury and investing in timeless, high-quality pieces that last a lifetime. Whether you’re looking for a classic winter wardrobe or simply want to channel elegance in your everyday look, the old money style offers an effortlessly sophisticated guide to dressing.

FAQ’s

  1. What colors define the old money aesthetic? Neutral tones such as navy, beige, grey, and black are essential to achieving the old money look.
  2. Are logos acceptable in the old money style? No, the old money style avoids flashy logos and focuses on understated elegance.
  3. What are some must-have old money winter pieces for men? A wool overcoat, cashmere sweater, and polished leather boots are essential for a refined winter wardrobe.
  4. Can I wear jewelry in the old money aesthetic? Yes, but it should be minimal and elegant, such as pearls, small diamonds, or gold pieces.
  5. Which fabrics best represent the old money aesthetic? Fabrics like wool, cashmere, silk, and tweed are staples in the old money wardrobe.
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