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“Old Money” Style: Fall Edition

Let’s Breakdown The “Old Money” Look

This fall, the “old money” aesthetic is making waves, drawing from styles that focus on class, timelessness, and quality over flash. This look is inspired by traditional, understated luxury—think neutral tones, classic cuts, and quality fabrics.

Below, discover five staple pieces every gentleman needs to achieve that quintessential “old money” look for the fall season, complete with proper styling tips and shopping suggestions.

Now that we have a grasp of some of the core elements involved with this classic and current trending “look”, let’s get into 5 statement pieces that will bring this look together, without overdoing it.

The “Core 4” Old Money Fall Pieces

1. The Heritage Tweed Blazer

The tweed blazer is an essential piece in an “old money” wardrobe. With its rich texture, classic fit, and durable material, a quality tweed blazer can make a statement on its own or as part of a layered ensemble. — so let’s break it down.

How to Wear It:

• Dressed Up: Wear with wool trousers and a clean dress shirt for a sharp look that’s not too formal.

• Casual Refinement: Pair with dark denim and a cable-knit sweater for a more laid-back, yet polished style.

Where to get Yours:

• Brooks Brothers: Known for traditional, high-quality blazers in classic patterns.

• J.Press: Offers a wide range of tweed blazers that exude Ivy League charm.

2. Cable-Knit Sweater: The Cozy Essential

A thick, cable-knit sweater in neutral shades like cream, navy, or gray is perfect for cooler temperatures. This piece is versatile and brings a sense of luxury and heritage that’s key to the “old money” aesthetic.

How to Wear It:

• Classic Look: Layer over a crisp white button-down and wear with tailored trousers.

• Smart Casual: Combine with chinos or corduroys and loafers for a sophisticated yet comfortable outfit.

Where to Buy:

• Ralph Lauren: Known for quality knits with timeless designs.

• L.L. Bean: Offers durable, affordable cable-knit sweaters with a heritage feel.

3. Tailored Wool Trousers

A well-fitted pair of wool trousers in neutral tones is a classic piece that provides both warmth and a taoilored silhouette. Opt for classic cuts that taper slightly at the ankle for a sleek look that’s not too fitted. (no skinny pants)

How to Wear It:

• Dressed Up: Pair with a tweed blazer and leather loafers for a complementary, formal look.

• Everyday Wear: Combine with a cashmere sweater and ankle boots for a more relaxed take.

Where to Buy:

• Paul Stuart: Known for luxurious, well-tailored pants that capture timeless elegance.

• Uniqlo: Offers affordable yet stylish wool-blend trousers in classic fits.

4. Leather Loafers: Timeless Footwear

Leather loafers are versatile, sophisticated, and comfortable, making them ideal for both casual and formal occasions. The “old money” style favors classic penny or tassel loafers in deep brown or black.

How to Wear It:

• Formal Occasions: Pair with wool trousers and a blazer for a sharp look.

• Weekend Wearing: Wear with dark jeans and a sweater for a polished yet casual outfit.

Where to Buy:

• Gucci: Known for their iconic loafers that exude timeless style.

• Allen Edmonds: Provides high-quality leather loafers with a traditional look and feel.

Let’s Bring This Look Together

Styling Tips for an “Old Money” Fall Wardrobe

Combining these timeless pieces will create numerous outfits that reflect the “old money” aesthetic.

For a complete look, start with wool trousers, layer on a cable-knit sweater, and top with a tweed blazer.

Finish the ensemble with leather loafers and a clean and subtle wristwatch for a look that turns heads.

The beauty of these pieces is in their versatility.

Each item can be paired with other fall wardrobe essentials for a look that’s both classic and masculine. When building this wardrobe, prioritize quality and fit to achieve the effortless aesthetic of the “old money” style.

Final Thoughts: Invest in Timeless Elegance

The “old money” aesthetic is more than a trend—it’s an investment in timeless pieces that will serve you for years to come.

Choosing quality over quantity and focusing on classic styles ensures that your wardrobe remains classy and versatile, no matter the season.

💡 Quick Tip: Explore the brands mentioned above for further inspiration. Their websites often feature styled looks that can help you envision these items in action. Whether you’re new to this style or looking to upgrade your existing wardrobe, these staples will help you embody classic fall menswear for a truly high-class look.

✏️ Note: For additional styling ideas and visuals, consider browsing these brands online, where they showcase season-specific looks featuring these staple pieces.

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