Dressing like 'old money' isn't just about wealth; it's about sophistication, timeless elegance, and a refined style that speaks volumes without saying a word. In this guide, we’ll explore the fundamental rules and essential wardrobe items needed to create an old money look that’s both polished and professional.

Table of Contents

• How To Dress Old Money Style 👔
• Rule #6: Accessorize Wisely 🎩
• Rule #7: Confidence is Key 💪
• Basic Item #1: Suits 👔
• Basic Item #2: Dress Shirts 👕
• Basic Item #3: Blazers & Sports Jackets 🧥
• Basic Item #4: Shoes 👞
• Basic Item #5: Polo Shirts 🏌️
• Basic Item #6: Neck Ties 🎀
• Basic Item #7: Khakis 👖
• Basic Item #8: Accessories 🎩

How To Dress Old Money Style 👔

Dressing in the old money style is about more than just the clothes you wear; it’s a representation of a lifestyle steeped in tradition and sophistication. To achieve this look, one must embrace a few fundamental principles that define the essence of old money. Let's break down the key rules that will help you dress like you belong to the elite class without screaming for attention.

Rule #1: Quality over Quantity 💎

The cornerstone of an old money wardrobe is the principle of quality over quantity. It's not about having a closet full of clothes; it's about owning a few exceptional pieces that stand the test of time. Look for fabrics that feel luxurious against the skin, such as wool, cashmere, and high-quality cotton.

• Invest in fewer, high-quality items rather than a multitude of cheaper options.
• Learn to identify quality craftsmanship—check seams, stitching, and fabric weight.
• Consider thrift stores or vintage shops for timeless pieces that might have been overlooked.

Rule #2: Timeless Elegance Over Trends 🕰️

Fashion trends come and go, but timeless elegance remains. Old money style favors classic silhouettes and traditional patterns that have proven their worth over decades. Instead of jumping on the latest fashion bandwagon, invest in pieces that have a history and will continue to be relevant.

• Opt for classic styles like tailored blazers, wool trousers, and button-down shirts.
• Choose neutral colors that can be mixed and matched easily, ensuring versatility in your wardrobe.
• Remember, a well-fitted navy blazer or a crisp white shirt can be your best friends for any occasion.

Rule #3: Focus on the Fit 🎯

No matter how expensive your clothes are, if they don't fit well, they won't look good. Tailoring is essential in the old money style. A well-fitted suit or jacket can elevate your appearance significantly. Always prioritize fit when shopping for clothing.

• Invest in a good tailor who can adjust your clothes to fit your body perfectly.
• When trying on clothes, pay attention to how they feel; comfortable clothing enhances confidence.
• Remember, a suit that fits well can make you look polished and put-together.

Rule #4: Stick with a Conservative Color Palette 🎨

A conservative color palette is a hallmark of the old money aesthetic. Stick to classic colors like navy, charcoal, beige, and white. These colors are timeless, versatile, and convey a sense of sophistication.

• Over 90% of your wardrobe should consist of these classic shades.
• Incorporate subtle patterns like houndstooth or pinstripes for added depth without overwhelming your outfit.
• Remember, the goal is to create a cohesive and polished look that doesn't distract from your overall presence.

Rule #5: Maintain Your Clothing & Accessories 🧴

Taking care of your wardrobe is crucial in the old money ethos. Quality clothing can last for decades if properly maintained. This means regular cleaning, repairs, and proper storage.

• Invest in a good shoe care kit to keep your leather shoes in pristine condition.
• Learn basic sewing skills to repair loose buttons and minor tears.
• Store your clothes properly to avoid damage—use breathable garment bags for suits and jackets.

Rule #6: Accessorize Wisely 🎩

Accessorizing in the old money style is about subtlety and elegance. You want to enhance your outfit without overwhelming it. The key is to choose timeless pieces that reflect your sophistication.

• Opt for a classic leather briefcase or a well-crafted backpack. These should be functional yet stylish, suitable for both work and leisure.
• Watches should be understated. A simple, elegant timepiece can make a statement without being flashy.
• Jewelry should be minimal. Think classic cufflinks or a simple ring—nothing oversized or trendy.

Rule #7: Confidence is Key 💪

Confidence in your style comes from knowing your wardrobe inside and out. Practice wearing your outfits until you feel completely at ease. When you know you look good, it shows.

• Wear your chosen pieces regularly. This will help you become familiar with how they fit and feel.
• Receive compliments and use them to build your confidence. Understand what works for you and why.
• Remember, your clothing should enhance your presence, not distract from it. Feel like a million bucks in what you wear.

Basic Item #1: Suits 👔

A suit is the cornerstone of any old money wardrobe. It should fit well and be made from high-quality materials. Look for suits that are versatile enough to wear on various occasions.

• Start with classic colors: charcoal, navy, and medium gray. These are timeless and can be mixed with various shirts and ties.
• Choose a suit that has a comfortable fit. It should allow for movement without being overly structured.
• Consider a subtle pattern, like herringbone, for added interest while maintaining versatility.

Basic Item #2: Dress Shirts 👕

Dress shirts are essential for creating a polished look. You should have a variety of colors and styles to pair with your suits.

• Stick with classic colors like white and light blue. These will work well with almost any suit.
• Experiment with collar styles. Button-down collars are great for casual settings, while spread collars are ideal for more formal occasions.
• Don’t shy away from subtle patterns, like thin stripes. They add a layer of sophistication without being overpowering.

Basic Item #3: Blazers & Sports Jackets 🧥

Blazers and sports jackets should be staples in your wardrobe. They provide a more relaxed yet stylish alternative to a full suit.

• Invest in a navy blazer. It's versatile and can be dressed up or down depending on the occasion.
• Look for breathable materials, especially for warmer months. Lightweight fabrics will keep you comfortable.
• Pair blazers with chinos or tailored trousers for a refined, casual look.

Basic Item #4: Shoes 👞

Quality footwear is crucial in completing your old money look. Each pair should be versatile and complement your suits and casual wear.

• Invest in classic Oxfords. They are timeless and suitable for formal occasions.
• Consider brogues for a slightly more casual vibe. They add character without sacrificing elegance.
• Loafers are also a great addition. They can be dressed up or down, making them perfect for various settings.

Basic Item #5: Polo Shirts 🏌️

Polo shirts are a versatile addition to the old money wardrobe. They strike the perfect balance between casual and refined, making them suitable for various occasions, from brunch to casual Fridays at the office.

• Choose high-quality fabrics like Pima cotton or merino wool for a luxurious feel.
• Stick to classic colors such as white, navy, and light pastels. These colors will complement your existing wardrobe.
• Avoid overly bright patterns or logos; the key is to keep it understated and elegant.

Basic Item #6: Neck Ties 🎀

Neck ties remain a staple in the old money aesthetic. They add a touch of sophistication to any outfit, making them essential for formal occasions and professional settings.

• Opt for classic styles like regimental stripes or subtle paisleys. These patterns convey tradition without being overly flashy.
• Stick to muted colors. A navy tie or a deep burgundy can elevate your ensemble while keeping it timeless.
• Invest in a few high-quality ties. A well-made tie can last for years and adds a polished touch to your look.

Basic Item #7: Khakis 👖

Khakis, or chinos, are an essential part of the old money wardrobe. They offer a smart-casual option that can be dressed up or down depending on the occasion.

• Choose a tailored fit that flatters your body shape. A well-fitting pair of khakis can make a world of difference.
• Stick to neutral colors like beige, olive, and navy. These colors can easily be paired with various tops.
• Consider different fabrics, such as twill or moleskin, for added texture and sophistication.

Basic Item #8: Accessories 🎩

Accessories can enhance your old money style, but they must be chosen wisely. The right pieces can complete your look without overwhelming it.

• Invest in a classic leather belt that matches your shoes. This creates a cohesive look.
• A pocket square is a subtle way to add personality to your outfit. Opt for a simple white linen square for timeless elegance.
• When it comes to watches, choose understated designs over flashy brands. A classic watch can be a statement piece without being ostentatious.