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Tailoring and Fit Guide to Achieve an Impeccable Old Money Look

In the world of classic menswear, the Old Money aesthetic is synonymous with timeless elegance, understated luxury, and impeccable tailoring.

At The VOU, we understand that achieving the perfect fit is the foundation of any successful old money-inspired ensemble.

In this comprehensive guide, we’ll delve into the intricacies of tailoring and fit within the context of the old money aesthetic.

We’ll explore the differences between classic and modern fits, discuss the importance of selecting the right fabrics and colors, and highlight common fit mistakes to avoid.

Whether you’re a seasoned enthusiast of the Old Money style or just beginning to build your wardrobe, this article will provide you with the knowledge and tools necessary to achieve the perfect fit every time.

Old Money Styling Tailoring Rules

Tailoring is an art form that requires a keen eye for detail, a deep understanding of proportions, and a commitment to quality craftsmanship.

The right fit can elevate a simple outfit to new heights, while ill-fitting garments can undermine even the most expensive and well-coordinated looks.

Well-fitted garments look more polished and put-together and convey a sense of quiet confidence and sophistication.

Below are the most important tailoring rules that ensure your clothes fit your body perfectly, highlighting your best features and minimizing flaws.


  • Wear classic, slim-fit suits in navy or charcoal
  • Ensure the shoulder seams sit at the edge of your shoulders
  • The jacket should be fitted through the torso but allow easy movement
  • Sleeves should end at the wrist bone, allowing 1/4-1/2 inch of shirt cuff to show
  • Trousers should have a slight break at the ankle, grazing the top of your shoes


  • Choose classic fit shirts from high-quality cotton or linen
  • Ensure the collar sits comfortably around your neck with room for two fingers
  • Shoulder seams should align with your shoulders
  • Sleeves should be fitted but not tight, ending at your wrist bone
  • The shirt should be long enough to stay tucked in throughout the day


  • Opt for a slim or straight-leg fit in a wool or cotton blend
  • The waistband should sit comfortably at your natural waist, not below
  • Seat and thighs should be fitted but allow easy movement
  • The hem should have a slight break, grazing the top of your shoes
  • Avoid overly trendy styles like skinny or wide-leg fits

Classic vs. Modern Fits

While both classic and modern fits can work within the aesthetic, classic fits tend to align with the timeless, traditional vibe of Old Money style.

Classic fits feature relaxed, comfortable silhouettes that drape elegantly on the body.

They’re not baggy or oversized but rather skim the frame in a flattering way.

Modern fits, on the other hand, tend to be slimmer and more form-fitting.

Ultimately, the choice between classic and modern fit comes from personal preference and body type.

If you’re lean and tall, a modern fit may suit you well.

If you have a larger frame or prefer a more relaxed look, classic fits may be the way to go.

Right Fabrics and Colors

In addition to fit, the fabrics and colors you choose play a significant role in achieving an Old Money look.

Opt for high-quality natural materials.

  • Wool for suits, blazers, and trousers
  • Cotton for shirts, chinos, and casual jackets
  • Linen for summer suits and shirts
  • Silk for ties and pocket squares
  • Cashmere for sweaters and scarves

When it comes to color, stick to a neutral palette of navy, charcoal, beige, and white.

These classic hues are timeless and easy to mix and match.

For a pop of color, incorporate small doses through your accessories, like a burgundy tie or green pocket square.

Fit Mistakes to Avoid

Even with the best intentions, it’s easy to fall prey to common fit mistakes that can undermine your Old Money style.

Below are a few fit mistakes you must watch out for.

  • Baggy or oversized fits – While classic fits are relaxed, they shouldn’t be baggy. Ensure your clothes skim your body without being too tight or loose.
  • Too short or too long sleeves – Your jacket and shirt sleeves should end at your wrist bone, allowing 1/4-1/2 inch of shirt cuff to show.
  • Pants that pool at your ankles – Your trousers should have a slight break at your ankle, grazing the top of your shoes without excess fabric pooling.
  • Neglecting alterations – Off-the-rack clothes rarely fit perfectly. Invest in alterations to ensure a custom-like fit.

Affordable Tailoring

Tailoring can be expensive, but there are affordable options for young men on a budget:

  • Look for local, independent tailors who offer competitive pricing
  • Consider made-to-measure services, which often cost less than bespoke
  • Invest in key pieces like a suit and overcoat, and spend less on casual items
  • Take advantage of seasonal sales and promotions to score deals on tailoring

Learn How to Style Old Money

But why go it alone? At The VOU, our team of expert stylists is here to help you navigate the world of Old Money fashion with ease.

Our styling packages are designed specifically for young men who want to elevate their look without breaking the bank.

Imagine the confidence and sophistication you’ll exude when you step out in perfectly tailored clothes that fit like a second skin.

With The VOU’s guidance, you’ll not only look like a million bucks but also feel like it.

Don’t settle for anything less than the best.

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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