Mastering the Art of Old Money Style: A Comprehensive Guide for Men

The “Old Money” aesthetic for men transcends fleeting trends; it’s a timeless style rooted in quality, understatement, and a quiet confidence. It’s not about displaying wealth ostentatiously but rather about expressing it through impeccable taste and subtle elegance. This guide will walk you through the key elements of achieving this refined look, offering detailed steps and actionable advice.

Understanding the Essence of Old Money Style

Before diving into specifics, it’s crucial to grasp the core principles of old money style. It’s characterized by:

• Quality Over Quantity: Invest in a few well-made pieces that will last for years rather than a closet full of cheap, trendy items.
• Understated Elegance: The focus is on classic cuts, subtle colors, and refined details, not flashy logos or attention-grabbing designs.
• Natural Fabrics: Embrace natural materials like cotton, linen, wool, and cashmere for their comfort, durability, and luxurious feel.
• Timelessness: The style avoids trends, prioritizing classic silhouettes and patterns that remain relevant year after year.
• Comfort and Fit: Clothes should fit impeccably, allowing for ease of movement and exuding confidence.
• Heritage and Tradition: Often, there’s an appreciation for pieces with a history, whether it’s a classic watch or a well-worn leather bag.

Building Your Old Money Wardrobe: Step-by-Step Guide

Here’s a detailed breakdown of how to curate an old money wardrobe, piece by piece:

1. The Foundation: Core Clothing Items

a. Suits and Blazers:

• The Navy Blazer: A cornerstone of old money style. Choose a classic, single-breasted blazer in navy wool, ideally with gold or silver buttons. It’s incredibly versatile and can be dressed up or down. Look for a natural shoulder, not heavily padded, and a fit that gently hugs your torso without being restrictive.
• The Gray Suit: A charcoal or medium gray suit in a fine wool is another essential. It should be well-tailored with a classic two- or three-button single-breasted cut. Avoid trendy, skinny fits, opting for a timeless, straight silhouette.
• The Tweed Blazer: For a more casual but equally refined option, consider a tweed blazer in a brown or green earthy tone. This is particularly appropriate for fall and winter. Look for details like elbow patches for an added touch of heritage.
• Fabric Considerations: Opt for wool, cashmere, and linen depending on the season. Super 100s to Super 150s wools are excellent for suits and blazers, offering a balance of durability and luxurious feel.
• Tailoring is Key: Never underestimate the importance of tailoring. A suit or blazer that fits perfectly will always look more expensive and refined than one that doesn’t. Invest in a good tailor who understands classic fits.

b. Shirts:

• The Oxford Cloth Button-Down (OCBD): This is a staple. Choose white, light blue, or pale pink for maximum versatility. The Oxford cloth is durable and slightly textured, giving it a more relaxed feel than a formal dress shirt. The collar should have a gentle roll.
• The Linen Shirt: For warmer weather, linen shirts in white, light blue, or beige are perfect. They are breathable, comfortable, and effortlessly stylish. Be aware that linen wrinkles easily, which is part of its charm.
• The Dress Shirt: For more formal occasions, opt for a classic white or light blue cotton dress shirt. Choose a high-quality fabric with a smooth finish, and ensure a perfect fit around the neck and shoulders.
• Avoid Loud Patterns: Steer clear of overly bold patterns or bright colors. Stick to solids or subtle stripes and checks.
• Collar Choice: A classic point collar or a button-down collar are the most appropriate for this style. Avoid trendy, overly wide or short collars.

c. Trousers:

• Chinos: A versatile staple, chinos in khaki, navy, olive, or gray are essential. Choose a straight or slightly tapered fit that sits comfortably on your waist and falls cleanly over your shoes. Look for a medium-weight cotton twill.
• Wool Trousers: For a more refined look, choose wool trousers in gray, navy, or charcoal. Look for a fabric with a good drape and a comfortable fit. These are suitable for both business and social settings.
• Corduroys: A great option for fall and winter, corduroy trousers in brown, tan, or green add texture and warmth. Choose a medium-wale corduroy for a classic look.
• Avoid Skinny Fits: Trousers should have a comfortable, classic fit with a straight leg or a slight taper. Avoid overly tight or skinny fits, as they are not in keeping with old money style.
• Length is Important: Trousers should break gently on your shoes, not pooling at the ankle.

d. Outerwear:

• The Trench Coat: A classic trench coat in khaki or navy is a timeless investment. Look for a well-made coat with a water-resistant fabric, a belted waist, and a traditional double-breasted design.
• The Wool Overcoat: For colder weather, a wool overcoat in navy, charcoal, or camel is essential. Choose a classic, single- or double-breasted design that falls to your knees or slightly below.
• The Barbour Jacket: For a more rugged, countryside look, a Barbour waxed jacket is a great choice. It’s durable, practical, and undeniably stylish. Choose the classic olive green color.
• Avoid Overly Trendy Styles: Steer clear of overly trendy or heavily branded outerwear. Stick to classic designs in high-quality materials.

e. Knitwear:

• Cashmere Sweaters: A cashmere sweater in navy, gray, or cream is a luxurious and versatile addition to your wardrobe. Choose a classic crewneck or v-neck design.
• Merino Wool Sweaters: Merino wool is a more affordable alternative to cashmere, offering excellent warmth and softness. Choose classic crewneck, v-neck, or cardigan styles.
• Lambswool Sweaters: A great choice for everyday wear, lambswool sweaters are warm, durable, and come in a variety of colors.
• Avoid Loud Graphics: Opt for solid colors or simple patterns like stripes or argyle. Avoid sweaters with large logos or bold graphics.

2. The Details: Accessories and Finishing Touches

a. Shoes:

• Leather Oxfords: A pair of well-made leather oxfords in black or dark brown is an absolute must. Choose a classic cap-toe or wingtip design.
• Leather Loafers: Leather loafers in brown or burgundy are another essential. They are versatile and can be dressed up or down. Choose penny loafers or tassel loafers.
• Suede Boots: Suede chukka boots or Chelsea boots in brown or tan are great for casual wear and add a touch of sophistication.
• Avoid Sneakers: While a pair of clean white minimalist sneakers can be acceptable in very casual settings, they are not generally part of the core old money style. Prioritize leather footwear.
• Quality Matters: Invest in high-quality leather shoes that will last for years. Take good care of your shoes and polish them regularly.

b. Belts:

• Leather Belts: Choose a high-quality leather belt in black or brown that matches your shoes. The buckle should be simple and understated, without any overly flashy designs.
• Width: The belt should be of an appropriate width for your trousers, not too wide or too narrow.
• Avoid Overly Casual Belts: Avoid overly casual canvas or fabric belts. Prioritize leather.

c. Watches:

• Classic Timepieces: Choose a classic watch with a leather strap or a metal bracelet. Simple, elegant designs are preferred. Brands like Rolex, Omega, and Patek Philippe are the benchmarks, but there are many excellent options at different price points.
• Avoid Overly Large Watches: Choose a watch that is proportionate to your wrist size. Avoid overly large or bulky watches.
• Subtlety is Key: The watch should be a subtle expression of your taste, not an ostentatious display of wealth.

d. Ties and Pocket Squares:

• Silk Ties: Choose silk ties in classic patterns like stripes, polka dots, or solid colors. Avoid overly trendy or bold designs. Navy, burgundy, and gray are excellent choices.
• Pocket Squares: A linen or silk pocket square adds a touch of sophistication. Choose simple patterns like solid colors, paisleys, or subtle geometrics.
• How to Wear Them: The tie and pocket square should complement each other but not match exactly. A puff or straight fold is typically preferred for pocket squares, avoiding overly complicated folds.
• Material Considerations: Stick to high quality silk and linen fabrics.

e. Other Accessories:

• Sunglasses: Choose classic sunglasses in styles like aviators, wayfarers, or tortoiseshell frames.
• Hats: For colder weather, consider a classic wool or cashmere hat. Avoid overly trendy or attention-grabbing hats. A baseball cap can be acceptable in some casual situations but generally is not in line with classic old money style.
• Socks: Choose socks in solid colors that match your trousers. Avoid overly loud or patterned socks. Over the calf socks are preferred to keep your legs covered when sitting.
• Wallets & Bags: Select a quality leather wallet and briefcase or bag that will improve with age. Avoid overly branded items.

3. Grooming and Demeanor: The Final Touches

a. Grooming:

• Well-Groomed Hair: Keep your hair neatly trimmed and styled. Avoid overly trendy or elaborate hairstyles.
• Clean Shave or Well-Maintained Beard: If you choose to have facial hair, keep it neatly trimmed and groomed.
• Basic Skincare: Take care of your skin with a simple skincare routine. Focus on keeping your skin clean and hydrated.
• Subtle Fragrance: Choose a classic and understated fragrance. Avoid overly strong or overpowering scents.

b. Demeanor:

• Confidence, Not Arrogance: Old money style is about quiet confidence, not ostentatious displays of wealth.
• Good Manners: Practice good manners and etiquette. Treat everyone with respect.
• Subtlety is Key: The style is about effortless elegance, not showing off. Avoid the need to draw attention to your outfit.
• Invest in Personal Growth: Develop a keen interest in the world and the arts. Pursue your education and maintain intellectual curiosity.

Key Takeaways and Final Thoughts

Achieving old money style is a journey, not a destination. It requires patience, careful planning, and an investment in quality. Here are some key takeaways:

• Start with the Essentials: Build a wardrobe based on the core items discussed above. Focus on quality and fit.
• Invest Wisely: Prioritize quality over quantity. It’s better to have a few well-made pieces than a closet full of cheap, trendy items.
• Don’t Chase Trends: Old money style is about timelessness. Avoid trendy pieces that will quickly go out of style.
• Pay Attention to Details: The small details, like the fit of your clothes and the quality of your accessories, can make a big difference.
• Be Authentic: The most important thing is to develop your own personal style and wear your clothes with confidence. It’s about presenting the best version of yourself, grounded in quality and taste.

By following these guidelines, you can cultivate a wardrobe that embodies the timeless elegance and understated confidence of the old money aesthetic. Remember, it’s not just about the clothes you wear, but how you wear them and how you carry yourself. It is a journey of developing taste and embracing heritage. It is a constant refinement of your personal expression.