The Only Old Money Style Guide You Need This Winter

As winter slowly crawls in, welcome timeless elegance the old money way. Discover the art of refined fashion, blending classic sophistication with modern warmth. From luxurious fabrics to iconic accessories, redefine your winter wardrobe with lasting style and grace.

Man Wearing a Camel Overcoat with Suit and Brown Leather Shoes Outfit

Trends can often be difficult to wear, particularly if they don’t seamlessly fit your unique proportions. Yet, as winter approaches and the clothing layers emerge, there is a golden opportunity to level up your wardrobe with the Old Money style.

What is Old Money Winter Style?

To begin taking advantage of this style, we need to understand the basics. Old Money Winter Style is all about looking refined, elegant, subtle, and classy mainly through wearing clothes containing excellent craftsmanship and simplicity.

Blame it on the crypto bubble or hit television shows, but many people around the world are leaping into the trend of Old Money.

TV shows like Succession, which wrapped up earlier this year after 4 seasons, have showcased how the ultra-wealthy suppress flashy clothing items like logos, and bright colors, and people were quick to notice.

To dress old money style, there are three primary principles:

  1. Stick to a basic color palette – Camel, gray, navy, black
  2. Invest in good quality pieces – Tweed, cashmere, pure wool
  3. Minimal Logos/designs – Simplicity = exclusivity
Succession' Season 3 Scene
Scene From the TV Series, Succession (Season 3)

The emphasis is quality over quantity. Think of brands like Polo Ralph Lauren, Loro Piana, Brunello Cucinelli, and Hermes, the four best old-money brands in my opinion.

Each piece will cost you more than your average clothing item, but the quality and versatility of these brands provide limitless styling options.

Essentials for the Old Money Winter Wardrobe

Man's Wardrobe

Winter brings a fresh chance to revamp your wardrobe. Whether you’re reusing from last season, or ready for a fresh shopping spree, we’ll help you find the essentials to look old money this winter.

1. Outerwear With a Timeless Appeal

Invest in outerwear that doesn’t just keep you cozy but tells a story with each thread. Options include classic wool coats, tweed jackets (embracing the English countryside), and perhaps a chic cape adorned with faux fur.

As we mentioned earlier, stick to neutral tones like navy, camel, or black to enhance versatility.

This is crucial as it’s a hero piece to your winter style look, meaning it must match other items in your wardrobe.

Outerwear, including jackets and coats, establishes the salient feature of your look during winter, so choose wisely.

Our pick:

Trench coat: An icon of military origin embraced by old-money enthusiasts worldwide.

With clean lines and a slim silhouette, you must pay attention to the length and quality of its fabric.

Choose a mid-thigh length and a water-resistant material for a combination of style and practicality.

2. Luxurious Knitwear for Cozy Elegance 

Elevate your wardrobe with a finer piece of cashmere or merino wool. Whether it’s a cable-knit sweater, a turtleneck, or a V-neck, opt for simplicity with simple patterns.

3. Tailored Trousers

Build the foundations of your outfit with well-fitted wool trousers. These classics can seamlessly pair with button-down shirts or turtleneck sweaters, offering a polished and sophisticated look. 

Chinos are also extremely versatile winter outfit options. Matching effortlessly with a clean polo shirt or a dress shirt, they allow for a mix of comfort and style, perfect for any smart-casual occasion. 

Mix it up with Khaki, black, or beige tones and match your polo shirt and a pair of polished loafers to complete a stylish, but warm old-money look.

4. The Dress Shirt: A Staple for All Winter Wardrobes

In the world of old money, particularly in winter, dress shirts play a very central role. They’re the cornerstone of classic style and a reflection of an individual’s taste.

Ensure you choose great quality such as Egyptian cotton, oxford, and linen for comfort, breathability, and longevity. Tailored fits are almost always better as they shape your body and erase a baggy look.

Old Money Outfit Including Light Blue Shirt and White Pants

5. Shoes

Every detail matters, and being the cold season, enclosed shoes are the obvious choice. A pair of Oxford shoes are non-negotiable for formal occasions.

They feature a closed lacing system and come in different materials and patterns but stick to black and brown leather if you are looking for a clean and versatile pair.

For a more casual, comfortable option, loafers are the old-money staple. Classic penny loafers or tassel loafers are both excellent choices to pair with any outfit and will also keep your feet warm.

6. Winter Accessories for the Extra Touch

Complete your money winter style look with scarves, leather gloves, berets, or elegant fedoras. These accessories not only keep you from getting the chills but also add a finishing touch to old-world charm for your winter attire.

When it comes to accessories you need to understand the art of understatement. Opt for accessories that radiate elegance without screaming for attention.

More options include cuff links, a brown leather wallet, and a classic timepiece. Check our classy watch guide article to get some ideas.

Style Inspiration for Each Winter Occasion

1. For the Cold Mornings

As the cold unfolds in the early hours of the morning, choose clothing that cocoons you in warmth. Wrap yourself in the luxury of a cashmere turtleneck sweater paired with wool pants and ankle boots. 

Additionally, cardigans are a great option when paired with black wool pants and boots.

2. For the Office

Woolen professionalism embraces tailored wool trousers paired with a classic button-down shirt for a polished look. 

For the corporate workers whose style choice is suited, ensure your collection has camel, gray, black, and navy. Also, consider subtle patterns like pinstripes to add more depth to your suit.

Patrick Adams and Gabriel Macht in Suits

With those 5 pairs, you can create over 75 suit pairings. To include the old money trend, throw on a turtleneck under your suits, or swap your boots for loafers for the more casual days. Take a leaf out of James Bond’s style book, who’s rocked the turtleneck for the last 6 decades.

For the less casual workers, a simple quarter zip sweater, in tan or navy, is the perfect complement to your work outfit.

3. For the Snow

Being winter, there will likely be snow. To adhere to the old-money winter trend, you need to take advantage, as you’ll be able to have more layers. 

More Layers = More options to showcase your style.

Embrace equestrian vibes with a Barbour jacket, pants, and tall boots for a day in the grand outdoors. For the boots, make sure you stick with leather.

4. For Dinner

From ballet to a formal dinner at home, showcase the timeless look with a tailored tuxedo ensemble. For most occasions, stick with black, as it exudes the highest sophistication, especially when fine dining. This pairs well with leather gloves for a refined touch.

Alternatively, opt for a crispy dress shirt, white or blue work best. Pair these with long-fitting pants and brown/tan loafers for an ultra-classy look.

Final Tips for Your Winter Wardrobe

1. Layering

One of the most crucial aspects of looking “old money” this winter is layering. It’s not merely about piling on clothes but a careful orchestration of textures, fabrics, colors, and styles. 

Begin your outfits with a well-fitted base, perhaps a tailored shirt or turtleneck as we mentioned earlier. Build outward on this with a vest, cardigan, or classic wool coat, and ensure you strike a harmonious balance of class and warmth.

The result? A refined, cozy look that stands the test of winter’s chill with timeless charm.

2. Vintage

Princess Diana Old Money Outfit, 1994

A core principle of the “old money” look is vintage clothing. Stemming from traditional cultures, the trend optimizes craftsmanship and detailing of bygone eras that stand out in a sea of contemporary outfits. 

Whether it’s a well-preserved tweed jacket, a classic trench coach, or a pair of distinguished leather gloves, vintage finds add a layer of authenticity to your wardrobe.

3. Inspirations

Many people embody this trend in their day-to-day clothing attire, particularly in the winter season. These icons not only navigate the chilly weather with grace but redefine class with every appearance.

Daniel Day-Lewis: The Oscar-winning actor boasts a quiet, yet unmistakable, refinement in his winter outfits, often seen donning tailored coats and classic accessories. 

Cate Blanchett: A standout for looking “old money”, Blanchett’s winter looks are a masterclass in balancing comfort and style, showcasing the power of well-chosen outerwear and subtle accessories. 

Eddie Redmayne: With a love for tailored suits and classic overcoats, Redmayne effortlessly captures the essence of old money style, offering a blueprint for winter sophistication. 

Grace Kelly: While a historical figure, the eternal style of the former Princess of Monaco remains a perennial inspiration. Her winter wardrobe, characterized by luxurious fabrics and impeccable tailoring, epitomizes enduring elegance. 

Tom Hanks: Known for his versatile style, Hanks often embraces old money charm in his winter attire, favoring tailored jackets, neutral tones, and sophisticated layers. 

Remembering the Old Money Fundamentals This Winter

Remember, less is more when it comes to the old money style. Though you will likely have many layers, be sure not to overcomplicate the look.

Keep minimum branding and steer clear of loud logos and you’re halfway there to harmonizing this aesthetic. 

Whether it’s a formal dinner, snow outing, morning walk, workday, or simply a cold morning, the old-money winter style provides a canvas for crafting a look that stands the test of time. With careful blends of classic pieces paired with modern touches, each outfit becomes a reflection of a time that once was.


The Only Old Money Style Guide You Need This Winter
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The Only Old Money Style Guide You Need This Winter
As winter comes, welcome timeless elegance with old money style. From luxurious fabrics to iconic accessories, redefine your winter wardrobe with this style.
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Midway Gentleman
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