How To Dress Old Money? | The Guide to Nailing the Expensive and Elegant Look

If you're looking to exude an air of old money, you've come to the right place. It's important to note that achieving an expensive and elegant look is not solely about the clothes you wear; it's about how you carry yourself. As a stylist, I will provide recommendations on fashion choices that will help you implement these tips into your everyday life. As a mindset coach and psychologist, I will also offer advice on how to not only LOOK old money, but FEEL it - because ultimately, mindset is key. To further assist you in your journey, I have created a free video guide entitled "The Old Money Mindset: A Guide to Achieving an Expensive and Elegant Look" that you can download :)


Allow me to share a bit about my background and why I am qualified to speak on this topic. Although I don't come from an old money family myself, it's something that I aspire to build for my own family. To be considered old money, one must have at least seven generations of wealth, a feat that is nearly impossible for me given that my family experienced dispossession during the Soviet era. However, my parents were able to build something new, and they possess a Jewish-Old-Money mindset that I also share. It's this unique perspective that allows me to offer valuable insights into the world of old money style and mentality.

#1. Quality Over Quantity

One of the key elements of dressing with an old money vibe is prioritizing quality over quantity. This means investing in timeless pieces made from natural fabrics like wool, silk, and cashmere. Stick to classic, neutral colors that never go out of style, and avoid trendy, flashy pieces that will quickly look dated.


Building a capsule wardrobe of versatile pieces is a great way to achieve an old money look. Choose high-quality, well-made items that can be mixed and matched, rather than fast fashion that will fall apart after a few wears. Keep in mind that investing in high-quality items doesn't necessarily mean spending a lot of money. You can often find classic, well-made pieces at vintage shops or consignment stores, or during sales at high-end retailers.


By prioritizing quality and classic choices, you can create a wardrobe that exudes an air of elegance and sophistication, without relying on trendy or flashy pieces that quickly go out of style. Natural fabrics like wool, silk, and cashmere are not only luxurious to the touch, but they also have a timeless quality that reflects the old money mentality of valuing quality over ostentatious displays of wealth.


While dressing with an old money vibe involves prioritizing quality and classic choices, it doesn't mean you have to have a boring style. Classic items can come in different cuts, and it's important to find pieces that fit your personal style and make you feel confident.


Choosing well-made items in neutral colors like black, white, beige, and navy can provide a timeless base for your wardrobe, but don't be afraid to add pops of color or unique accessories to make your look your own. You can also experiment with different textures, like a wool blazer or a silk scarf, to add interest and depth to your outfits.


The key is to strike a balance between classic pieces and personal style, so that you look timeless but not outdated. By investing in high-quality items made from natural fabrics, you can create a wardrobe that will last you for years to come, while still expressing your unique personality and taste.

#2. Top Notch Details

To achieve an old money look, it's important to pay attention to the details of your outfit, including the hardware on your accessories and the buttons on your clothing. These small details may seem insignificant, but they can make a big difference in the overall impression of your outfit.


When choosing accessories like handbags, belts, and shoes, look for items with high-quality hardware, such as gold or silver-tone clasps and buckles. Avoid items with flashy logos or too much bling, as these can detract from an overall polished look. Instead, opt for simple, classic designs that will stand the test of time.


It's also important to pay attention to the patterns and fabrics in your outfit. When wearing multiple patterns, make sure they complement each other and don't clash. Stick to classic patterns like stripes, plaids, and houndstooth, and avoid overly trendy prints that may look dated in a few years.


When it comes to fabrics, focus on natural materials like cotton, wool, silk, and cashmere. These materials not only look and feel luxurious, but they also age well and can last for years with proper care. Look for items with high-quality stitching and finishes, as well as linings that are well-constructed and designed to last.


By paying attention to these small details and investing in high-quality, well-made pieces, you can achieve an old money look that exudes sophistication and elegance.

#3. Subtle High End Clothes

If you're looking to invest in high-quality clothing to achieve an old-money look, there are a number of brands that offer understated, classic styles that exude sophistication and elegance. These brands are known for their attention to detail, use of high-quality materials, and impeccable tailoring.


One such brand is Ralph Lauren, known for its timeless American style and classic designs. Other brands that offer high-end, classic clothing include Brooks Brothers, Burberry, Loro Piana, Brunello Cucinelli, Goyard, and Bally. These brands offer a range of clothing items, from blazers and trousers to dresses and accessories, all designed with a focus on quality, comfort, and sophistication.


When choosing high-end clothing brands, it's important to consider not just the price tag, but also the quality of the materials and the construction of the garment. Look for items with high-quality stitching, finishes, and linings, and consider investing in pieces that will stand the test of time.


I recommend to my clients to pick good quality clothes and invest in high-end bags, belts, watches, shoes, and accessories. Because these items actually create the whole difference. Here are some items I'd pick if the task was to create an old-money vibe.


Remember, achieving an old money look isn't just about the clothes you wear, but also about how you carry yourself and your attitude towards money and wealth. By investing in high-quality, classic clothing and taking care to choose items that complement your personal style, you can exude confidence and sophistication that will make you feel like a true member of the old-money elite.

#4. Investment Pieces for Generation to Last

Investing in items that can last for generations is an important aspect of achieving an old-money look. While high-quality clothing and accessories are certainly a part of this, there are other investment pieces to consider as well. Rather than investing in trendy bags or other fleeting fashion items, consider investing in something truly special that will hold sentimental or monetary value for years to come. This could mean passing down a family heirloom such as a golden ring with a gemstone, investing in an art piece, or purchasing a piece of furniture that will become a cherished family possession. By investing in timeless, high-quality items, you can create a legacy that will endure for generations to come.

#5. Confidence

One of the most important aspects of achieving an old-money look is confidence. No matter how expensive your clothing or accessories may be, if you don't feel confident and comfortable in them, the look will fall flat. Confidence comes from within and is not something that can be bought or worn. However, by investing in high-quality, classic pieces and paying attention to details, you can boost your confidence and feel great in your outfit. Remember that the way you carry yourself is just as important as the clothes you wear, so stand tall, make eye contact, and exude an air of quiet confidence. When you feel good in your own skin, it will show in everything you do.


Here are some tips I do to feel confident myself and hope they're going to help you too:


  • Speaking slowly: Speaking deliberately and at a measured pace can help you appear more thoughtful and confident.
  • Positive self-talk: Practice positive self-talk and focus on your strengths rather than your weaknesses.
  • Dressing for success: Wearing clothes that make you feel good and confident can have a big impact on your overall demeanor.
  • Maintaining good posture: Standing up straight and maintaining good posture can help you feel more confident and assertive.
  • Setting small goals: Setting achievable goals and accomplishing them can help you feel more confident in your abilities.
  • Learning new skills: Learning new skills and challenging yourself can help you feel more confident and accomplished.
  • Taking care of yourself: Taking care of your physical and mental health can help you feel more confident in yourself.
  • Surrounding yourself with positivity: Surround yourself with positive people and uplifting environments that support your growth and well-being.
  • Embracing failure: Embracing failure as an opportunity to learn and grow can help you develop resilience and confidence.
  • Celebrating successes: Take time to celebrate your successes, no matter how small they may be. This can help you build confidence and momentum towards achieving your goals.

#6. Good Manners & Etiquette

Good manners and etiquette are essential parts of projecting an old-money persona. This means being polite and respectful in social situations, knowing how to conduct yourself at the dinner table, and being aware of social cues and expectations. It's also about showing gratitude and appreciation, whether it's thanking someone for their time or sending a handwritten note of thanks. Dressing appropriately for the occasion is also key, like avoiding high heels for a winter hike or not wearing a tuxedo to a casual gathering. It's also important to avoid speaking too loudly or interrupting others in conversation. As someone who is passionate about building an old-money image for myself and my family, I have learned firsthand the importance of good manners and etiquette in creating an air of sophistication and elegance.


You don't need to overwhelm yourself but taking everyday actions can greatly impact your life. Here are some suggestions:


  • Dressing appropriately for the occasion: This means choosing clothes that are suitable for the event or setting. For example, wearing formal attire to a wedding, or dressing in business attire for a job interview. It also means considering the weather, time of day, and cultural norms. By dressing appropriately, you show that you respect the occasion and the people around you.
  • Sitting up straight at the table, eating with a closed mouth: Good posture and table manners convey a sense of respect for the meal and the company. By sitting up straight and keeping your mouth closed while chewing, you show that you are attentive and mindful of your surroundings. This makes others feel more comfortable and at ease around you.
  • Putting away your phone during social interactions: When you're in a social setting, it's important to be fully present and engaged with the people around you. By putting away your phone, you signal that you are giving your full attention to the conversation. This shows that you value the person and the interaction and that you are not easily distracted.
  • Maintaining eye contact when someone talks to you: Eye contact is a powerful way to communicate that you are listening and engaged with the person speaking. It shows that you are interested in what they have to say and that you respect them enough to give them your full attention.
  • Practicing common courtesies, such as saying "please" and "thank you": These small gestures go a long way in demonstrating respect and appreciation for others. Saying "please" and "thank you" shows that you value the other person and are grateful for their time and effort.
  • Maintaining good hygiene, including clean clothes: Good hygiene is a basic requirement for social interaction. By keeping clean and wearing clean clothes, you show that you respect yourself and those around you. This also demonstrates that you take pride in your appearance and take care of yourself.
  • Showing gratitude and respect to others: This includes being polite, showing kindness, and expressing appreciation for others. By being respectful and courteous, you show that you value other people's feelings and opinions. This creates a positive environment where everyone feels valued and respected.

#7. Politness & Kindness

Politeness and kindness are essential elements of projecting an old-money vibe. It's important to be courteous and respectful toward others, whether it's towards family members, friends, acquaintances, or strangers. Some simple ways to show politeness and kindness include:

  • Saying "please" and "thank you" regularly.
  • Holding doors open for others.
  • Offering your seat to someone in need, such as the elderly or pregnant women.
  • Listening actively and engaging in thoughtful conversation.
  • Being mindful of your tone and body language when communicating with others.
  • Being punctual and reliable.
  • Complimenting others sincerely.
  • Showing empathy and compassion towards others.
  • Volunteering and giving back to your community.

Small acts of kindness can go a long way in creating a positive impression on those around you, and it's a reflection of your character as a person. By incorporating these simple actions into your daily routine, you can become a kinder and more polite individual.


It's important to not only be polite and kind but also to be deliberate in choosing who you spend your time with. Old-money individuals often have a close circle of trusted friends and acquaintances, and they prioritize building meaningful connections with those who share their values and interests. They understand that their social circle reflects on their own reputation and brand, and they are intentional in cultivating relationships that align with their personal and professional goals. Being deliberate in your social interactions can also help you to avoid drama and unnecessary conflicts, which is a hallmark of a refined and sophisticated person.

#8. Limited Use of Color

When it comes to creating a luxurious and sophisticated wardrobe, it's important to have a limited use of color. This doesn't mean that you have to stick to only black and white, but rather be intentional with your color choices. Neutral colors such as navy, beige, grey, and white are timeless and elegant choices that can be easily mixed and matched. Light and pastel colors can also be associated with luxury, but it's important to choose high-quality fabrics to avoid a cheap and flimsy look.


That being said, it doesn't mean that you can't wear colors at all. You can add pops of color through accessories or color blocking, but it's important to have a cohesive look. When incorporating colors into your wardrobe, consider your skin tone and natural coloring. Certain colors can enhance your natural beauty, while others can make you look washed out or overly flashy. Knowing your color type can help you make better choices when it comes to selecting clothing items and accessories. Overall, limited use of color can give your wardrobe a polished and refined look that exudes luxury and sophistication.

#9. Education & Taste

Having education and taste are essential for creating a luxurious and sophisticated lifestyle. In my family, we made education a top priority because it's the only thing that can't be taken away from us. It's not just about attending prestigious schools or having a degree, but rather about having an open mind and being curious about the world around us.

A well-rounded education can include reading books, traveling, attending cultural events, and having discussions with people from different backgrounds and perspectives. Taste, on the other hand, refers to having a refined sense of style, art, music, and design. It's about having an eye for quality and beauty, and being able to appreciate the finer things in life.

Developing taste takes time and effort, but it's a worthwhile investment in creating a luxurious and fulfilling life. By having education and taste, we can make informed choices when it comes to fashion, interior design, travel, and entertainment. We can also cultivate our own personal style, and express ourselves in a way that reflects our unique personalities and values.


Here are some examples of how to cultivate education and taste:

  • Reading books on a variety of topics, including history, literature, art, and philosophy
  • Visiting museums, galleries, and cultural events
  • Listening to a variety of music genres and attending concerts and shows
  • Traveling to different countries and immersing oneself in the local culture
  • Exploring different cuisines and learning about food and wine pairings
  • Collecting art or other objects that have personal meaning and value


By continuing to learn and explore the world around us, we can develop our education and taste, and create a luxurious and fulfilling lifestyle that reflects our unique perspectives and values.

#10. Prioritize experiences and relationships over material possessions

One final point to cultivate an old-money vibe is to prioritize experiences and relationships over material possessions. Old-money families are known for valuing tradition, heritage, and family legacy. They understand those material possessions come and go, but experiences and relationships are what truly matter in life.


This means that instead of spending money on expensive cars, designer clothing, or lavish homes, old-money individuals may choose to invest in experiences like travel, education, or cultural events. They may also prioritize building and maintaining relationships with family, friends, and community members.


By focusing on experiences and relationships, old-money individuals are able to create a sense of purpose and fulfillment that goes beyond material possessions. They are also able to pass on these values to future generations, creating a lasting legacy of culture, tradition, and wisdom.

It's important to remember that while cultivating an old-money lifestyle can bring a sense of sophistication and elegance, it's ultimately about creating a life that brings happiness and fulfillment. It's essential to ask yourself what your ultimate goals are and what you want to pass on to future generations.


The pillars of good manners, education, taste, and financial management can all help to create a life that aligns with your values and goals. By prioritizing these aspects, you can achieve success not only in material terms, but also in personal growth and relationships.


At the end of the day, it's crucial to find joy and satisfaction in your life. Whether that's through pursuing a passion, spending time with loved ones, or making a positive impact on your community, it's important to stay true to your values and strive towards the life you truly desire.


So, while following the principles of an old-money lifestyle can bring a sense of refinement and elegance, it's essential to keep in mind that these are simply tools to help achieve a fulfilling life. By prioritizing your own happiness and staying true to yourself, you can create a life that reflects your unique personality and values.

Free Video Masterclass + PDF Guide "Old Money Mindset: A Guide to Achieving an Expensive and Elegant Look" 

If you're someone who is interested in embracing the Old Money mindset and lifestyle, then I highly recommend tuning into my upcoming FREE masterclass titled "Old Money Mindset: A Guide to Achieving an Expensive and Elegant Look." In this free masterclass, I share valuable tips and insights on how to achieve a luxurious and sophisticated look without spending a fortune.


By joining me for this masterclass, you'll learn how to cultivate good manners, confidence, and etiquette, as well as tips on dressing appropriately for different occasions, developing your taste and education, and much more. It's the perfect opportunity to take your style and lifestyle to the next level and start living the Old Money way.


So mark your calendars for May 9th, when this masterclass will be available for you to watch. And don't forget to click the button below to sign up and get access to a small PDF that goes along with the masterclass. I can't wait to share this journey with you toward a more elegant and luxurious life.

Watch Free Masterclass & Get PDF Guide