Look Expensive The “Old Money” Way: A Lookbook

The way the internet understands the old money aesthetic is primarily based on their looks; after all, it is a fashion trend more than a lifestyle trend. Fascinations with aesthetics of, academia, old money, silent luxury, coastal grandmother, and the recent addition of “stealth wealth.” Old money is heavily based on preserving traditions, prestigious legacy, and a lineage of ideals that are only applicable to individuals coming from generational wealth. Stealth wealth, on the other hand, includes the Nouveau Riche or newly rich people who are not born wealthy but managed to get rich in their life; think Mark Zuckerburg or Steve Jobs and others. Their brand is preserved by looking relatable and grounded; but when you look closely, their way of looking rich is by wearing regular-looking clothes which cost a fortune and cannot be purchased by the common man.

As Gen Z is beginning to enter the workforce; they are met with the reality of the world at a much harsh speed. With the constant downfall of the economy, Gen Z is forced to let go of their maximalist and creative capacities to focus on the practicality of life. Clothing that is easy to pair, easy on the eye, functional to their day-to-day needs, and resembles the looks of high society style. Overall simplicity and the comfortable yet professional appeal of the old money are what attracted the younger generations to this style. These styles include blazers in shades of beige, gray, and off-white.

Look #1: Classic

The first and foremost rule of dressing up as someone who comes from generational wealth is by sticking to the classics. A classic silhouette, an ol timely charm patterns, and materials. Old money styling is all about timelessness and traditional styles. And nothing is as classic as a simple midi-length shirt dress with block heels. This is perfect for any universal occasion. Wear it to work, brunch, dates, the beach, and movies and you will never look overdressed or underdressed. Classic silhouettes take out the element of “appropriateness” since they are perfect for every single occasion at any time of the day.

Look #2: Modest

As suggested, old money is about preservation and classic styling. Which involves modesty as an unspoken rule of the style. Skirts and dresses hemlines rarely, or preferably never cross the knees. This paves for a more sophisticated and polished style without adding too much effort. Modest clothing is generally also synonymous with minimalist style where the importance is laid on the comfort of the clothing rather than having to constantly adjust your clothes while sitting or walking. Modest clothing has also become a popular phenomenon against the light of Y2K mini skirts. This is also a great style inspiration for people working in work sectors with strict dress codes.

Look #3: Monochrome

Minimalism loves simple outfits that don't take much time to put together. In the case of old money looks; looking put together is essential and one way to do so is by wearing a monochrome look. Commonly we see people wearing monochromatic black outfits to ensure that they look put together throughout the day and avoid getting their clothes looking messy or dirty in the process; however, in the world of old money looks; the monochromatic looks are generally of light colors- like beige, off-white and ivory. This is because the actual rich don't work or run around in public transport like we do; nor do they do their laundry. But feel free to experiment with the color palette of your preference as this is just a style guide.

Look #4: Relaxed

How would you feel if you did not have to worry about your money ever running out or your job? Relax right? That is exactly what is also reflected in the elite style; they want to stay comfortable because they are comfortable. But finding clothes that feel comfortable does not mean you see them in sweatpants everywhere. In fact, in many communities, sweatpants are looked down upon and not even considered loungewear. For a 24/7 relaxed fit, invest in linen pants and shirts. Flats that don't come with embellishments, because while they look better, they may just look tacky when the embellishments start falling off. Invest in capris or shorts but pair them with shirts and structured outwear companions. And don't forget your accessories, they can make or break your look.

Look #5: Simple

Simplicity is luxury and a well-made outfit looks best when it's simple. Putting together many accessories or logo-manic clothing shows that you are insecure about your wealth. When in reality you dress for functionality and dealing with too many accessories or ridiculous embroideries defeats the purpose of looking professional and chic. Reserve your outfit with 1-2 pieces of jewelry like simple earrings or a dainty necklace are the most opted choices for dressing up simply. This makes you look more put together and effortless, since you are just mix-matching the already simpler, solid-colored, and structured pieces in your wardrobe.

Look #6: Tailored

Ever wondered how even the most basic blazers and shirt-trouser combinations look so perfect and ethereal on some people? Especially when you see shows like Succession and how despite looking simple, the characters manage to look put together and “clean”. It’s primarily because the majority of celebrities and rich people, in general, get their clothes custom-made to fit them perfectly. When you wear tailored clothes, all the awkward bumps and foldings get fixed to suit you. Not all of us can afford to have all tailor-made clothes, but a simple hand stitch to tuck in awkward loose sides of a blazer, trouser, or dress can immensely change how you look in even store-bought clothes.

Look #7: Professional

So a majority of the clothes that the old money aesthetic is associated with are typical professional clothes that we grew up thinking were only limited to the workspace. Even for casual or vacation looks, this look rarely encourages casual street-style clothing. Meaning basically that looking clean, poise, and professional at all times is essential. So the easiest way to look professional immediately even when you are just going out with a few friends is to include a cardigan and loafers. It gives the perfect business casual look without looking stuffy.

Look #8: Refined

Timelessness and quality are preferred over trendy and fast fashion pieces which in turn make a person look put together and refined. Refined is at the core of old money or silent luxury style; which means carefully picking out what you want to include in your wardrobe. Not all expensive pieces are good quality but spending time to consider what you want to buy and what suits you and your lifestyle better will save you from ending up with a wardrobe full of clothes that you don't like. Avoid trendy or flashy pieces of clothing and accessories and invest in clothes that are durable and look refined.

Look #9: Powerful

In the 1980s, when preppy style became popular amongst the general upper and middle class of America, everyone was dressing for professional success. Men in suits had been a common sight in the professional atmosphere, but women who had started getting more career opportunities and leadership roles ditched the secretary skirts for pantsuits. It was the era of power dressing. Similarly, now, the casual office dress code has been locked outside the office premises with everyone from university students and young working professionals adapting to dress “for the role”. Including a darker color palette, stiletto heels, structured handbags, and business casual attire is the new power dressing. This is also in response to the old money style or 80s preppy style where looking for wealth ensures that you are also welcoming more professional success.

Look #10: Relaxed

You would be surprised how relaxed you look and feel when you don't have to constantly adjust how you look or how uncomfortable tight pants or mini skirts are. The idea is when you are comfortable you can focus on other aspects of your life more efficiently. And sticking to classics that are tailored to look appropriate for every occasion, you tend to be more relaxed, confident and look more approachable.