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Fastest Way to Build Your Own Personal Old Money Style – Gent’s Guide

In the world of men’s fashion, where trends come and go, originality reigns supreme and the true Old Money style is unique to each individual.

The essence of the Old Money style, a look that transcends fleeting trends and embodies effortless elegance, is about expressing your personality, confidence, and status through your clothing choices.

The Old Money aesthetic isn’t about flashy logos or following the latest fads but about dressing your body shape with the right clothes and colors in a way that complements your age and personality.

It’s a style that whispers sophistication, not shouts it.

Consider Your Body Shape

Understanding your body shape is crucial to dressing well.

The most expensive clothes won’t look good if they don’t fit properly.

In fact, ill-fitting clothes can accentuate your flaws rather than camouflage them.

The key to dressing for your body shape is to create balance and proportion.

This means choosing clothes that highlight your assets and downplay your flaws. Here’s how to dress for different body shapes:

Large Men

If you’re a larger man, avoid baggy clothes as they can make you look bigger.

Instead, opt for well-fitted clothes in dark colors like black, navy, brown, and grey.

Vertical patterns and pinstripes can help elongate your silhouette.

Choose relaxed-fit trousers and single-breasted jackets, and avoid turtlenecks in favor of V-neck jumpers and T-shirts.

Thin Men

If you’re a thin man, avoid very tight-fitted clothes and head-to-toe dark colors.

Light colors like white, cream, and pastels can add bulk to your upper body.

A contrast between dark pants and a light top can break up the “beanpole” look.

Horizontal stripes can also create the illusion of width, as can a double-breasted jacket.

Short Men

If you’re a shorter man, avoid stark color contrasts between your top and bottom half.

Instead, choose colors from the same family to create a fluid, elongated look.

For example, pair blue denim jeans with a dark blue top or khaki shorts with neutral, earthy colors.

Avoid large prints and opt for thin vertical stripes.

Steer clear of heavy twill fabric for jackets, and ensure your pants are tailored with a plain hem and no cuff or tapering.

Tall Men

If you’re a tall man, avoid both oversized and tight-fitting clothing.

Contrasting colors can help break up your long line, so pair different colored shirts and pants.

Straight-legged trousers and jeans, coupled with wide belts, can help balance your proportions.

Double-breasted jackets with wide ties can also work well.

Choose the Right Colors

The colors you wear can significantly impact your overall appearance.

The right colors can make you look healthier and more vibrant, while the wrong colors can wash you out.

Understanding Your Skin Tone

The first step to choosing the right colors is understanding your skin tone. There are three main categories: warm, cool, and neutral.

  • Warm: If you have warm undertones, your skin will have a yellow or golden hue. You’ll likely look best in earthy tones like brown, olive green, camel, and ivory.
  • Cool: If you have cool undertones, your skin will have a pink or blue hue. You’ll likely look best in cooler colors like grey, pale blue, navy, green, and khaki.
  • Neutral: If you have neutral undertones, your skin won’t have a yellow or pink hue, so you’re lucky to be able to wear a wide range of colors.

Choosing Colors for Your Wardrobe

Once you understand your skin tone, you can build a wardrobe that complements it.

Here are some general guidelines:

  • Dark Skin: Men with dark skin often look best in bright colors and shades of white. Sapphire blue, ruby red, and bold colors like orange and green can also be good choices.
  • Olive to Medium Skin: Men with olive to medium skin tones often look best in earthy tones like brown, olive green, camel, and ivory.
  • Light Skin: Light-skinned men often look best in cooler colors like grey, pale blue, navy, green, and khaki.

By choosing the right colors and incorporating them into your wardrobe in a thoughtful way, you can achieve a look that is both sophisticated and uniquely you.

The General Old Money Palette

The Old Money style favors a classic and understated color palette.

This means sticking to neutral colors like navy, grey, brown, and white and incorporating subtle pops of color through accessories like ties and pocket squares.

These colors are not only timeless and elegant, but they’re also incredibly versatile.

They can be easily mixed and matched to create a variety of looks, making them a practical choice for any wardrobe.

Find Your Fit

The Old Money style emphasizes well-fitted clothes tailored to your body shape.

This means avoiding anything too baggy or too tight. Your clothes should skim your body without clinging to it.

A well-fitted suit is a cornerstone of the Old Money wardrobe.

The jacket should hug your shoulders without being too tight, and the trousers should fall straight from the hips without being too baggy.

Remember, the goal is to create a balanced and proportionate look.

By understanding your body shape and choosing clothes that flatter it, you can achieve a stylish, sophisticated, timeless, and effortless look.

Size Does Matter – Know Your Exact Measurements

Knowing your exact measurements is crucial for buying clothes that fit well.

Whether shopping online, browsing the sales rack, or ordering clothes from overseas, having your measurements on hand will save you time and money.

Here’s how to measure yourself correctly:

  • Chest: Wrap the tape measure under your armpits and around the fullest part of your chest and shoulder blades.
  • Neck: Measure around the base of your neck, a few centimeters below your Adam’s apple.
  • Sleeve: Hold your arm straight out from your side and measure from your shoulder to your wrist joint.
  • Waist: Wrap the tape measure around your torso where you normally wear a belt.
  • Inseam: Measure from the crotch to the ankle bone.
  • Outer seam: Measure from the top of your waistband to the bottom of your ankle.
  • Foot: Measure the length and width of your foot while wearing socks.

Record your measurements in centimeters and inches, as different countries use different sizing systems.

If your weight fluctuates, it’s a good idea to re-measure yourself before each shopping trip.

The Importance of Tailoring

No matter how expensive your clothes are, they won’t look good if they don’t fit well.

Tailoring is essential for achieving a polished and put-together look.

Have your clothes adjusted to fit your body perfectly, and you’ll instantly look more stylish and sophisticated.

Dress for Your Age

As we age, our style should evolve with us.

Dressing too young can make you look immature while dressing too old can make you look out of touch.

The key is to find a balance that reflects your age and personality.


In your twenties, you’re still experimenting with your style.

This is the time to try new things and see what works for you.

However, it’s also important to start investing in quality pieces that will last.

A tailored blazer and a good quality dress shirt are good starting points.


By the time you reach your thirties, you should have a good sense of your personal style.

This is the time to refine your wardrobe and focus on quality over quantity.

Invest in well-made clothes that fit you well and avoid anything too trendy.


In your forties, it’s important to balance dressing too young and dressing too old.

Stick to reputable brands in simple colors and classic cuts. Invest in a high-quality trench coat.

Fifties and Beyond

In your fifties and beyond, prioritize smart-casual attire in dark or earthy hues.

Avoid sneakers, flashy jewelry, and overly revealing swimwear.

A tailored trench coat is a timeless investment.

Style Icons for Inspiration

Throughout the ages, there have been numerous style icons who have exemplified dressing for their age.

  • In your twenties, look to Zac Efron and Tinie Tempah for inspiration.
  • In your thirties, David Beckham and Ryan Gosling are great examples.
  • For your forties, consider Daniel Craig and Brad Pitt.
  • And in your fifties and beyond, George Clooney and Steve McQueen are timeless icons.

By observing these style icons and adapting their choices to your taste, you can develop a personal style that is both age-appropriate and uniquely you.

Remember, the goal is to look and feel your best at every age.

Add a Touch of Personality

While the Old Money style is known for its understated elegance, that doesn’t mean you can’t inject a bit of personality into your wardrobe.

You can do this by incorporating subtle patterns like stripes and checks or by adding a pop of color through your accessories.

For example, you could pair a navy suit with a light blue shirt and a patterned tie, or you could wear a white shirt with chinos and a colorful pocket square.

The key is to keep it subtle and sophisticated.

Remember, the goal is to create a look that is both stylish and timeless.

Key Styling Tips

Developing your own style is a process of experimentation and refinement.

It’s about trying different things, seeing what works, and gradually honing your choices. Here are some key tips to guide you:

  • Quality Over Quantity – Invest in high-quality, timeless garments from heritage brands. A few well-made pieces will serve you better than a closet full of trendy and cheap clothes and shoes.
  • Don’t Overdo It – Keep it simple and avoid over-accessorizing. Well-chosen accessories can elevate your look, but too many can make you look cluttered.
  • Comfort is Key – Always prioritize comfort. No matter how stylish an outfit is, it will show if you don’t feel comfortable in it.
  • Experiment – Don’t be afraid to try new things. Step outside your comfort zone and experiment with different styles, colors, and patterns.
  • Be Yourself –  The most important aspect of developing your style is staying true to yourself. Don’t try to be someone you’re not. Your clothes should reflect your personality and make you feel comfortable and confident.

Key Shopping Tips

For many men, shopping for clothes can be a daunting task.

However, with a little planning and preparation, it can be a breeze.

Here are some tips to make your shopping experience more efficient and enjoyable:

  • Do Your Research – Before you hit the shops, browse fashion magazines and websites to get an idea of what’s in style. This will help you narrow down your choices and avoid aimless wandering.
  • Know Your Measurements – Having your measurements on hand will help you choose clothes that fit well and save time in the fitting room.
  • Shop at Off-Peak Times – Avoid peak shopping times like weekends and evenings. Early mornings or weekdays are usually less crowded.
  • Make a List and Set a Budget – Decide what you need to buy and how much you’re willing to spend before you go shopping. This will help you stay focused and avoid impulse buys.
  • Dress for the Occasion – Wear clothes that are easy to change in and out of, like a T-shirt and slip-on shoes.
  • Ask for Help – Don’t be afraid to ask sales assistants for help. They can advise on fit, style, and what’s currently in stock.

The Art of Accessorizing

Accessories can elevate your look from ordinary to extraordinary. However, the Old Money style emphasizes quality over quantity.

A few well-chosen accessories, such as a classic watch, a pair of cufflinks, or a leather belt, can add a touch of personality and sophistication to your outfit.

Avoid over-accessorizing and opt for timeless pieces that will complement your wardrobe for years to come.

The Importance of Grooming

The Old Money style isn’t just about clothes.

Grooming plays a significant role in achieving a polished and sophisticated look.

This includes maintaining a well-groomed haircut, keeping your beard or mustache neat and trimmed, and caring for your skin.

Investing in quality grooming products and developing a regular grooming routine is crucial for maintaining a well-put-together appearance.

The Old Money Attitude

The Old Money style is more than just a way of dressing; it’s a way of life.

It’s about being respectful, polite, and well-mannered.

It’s about carrying yourself with confidence and grace and making a positive impression on those around you.

By adopting the old-money attitude, you can elevate your style and achieve a level of sophistication beyond fashion.

As the saying goes, “confidence is the ultimate accessory.”

The way you carry yourself can make or break your look.

Stand tall, make eye contact, and speak with conviction.

A confident demeanor can elevate even the simplest outfit and make you stand out from the crowd.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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