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Old Money Wardrobe Essentials for a Million Bucks Gentlemen Look

Today, we’re exploring the essential building blocks of a timeless, sophisticated wardrobe that whispers ‘refined taste’ rather than screaming ‘nouveau richer.’

But first, let us share a little secret: crafting an Old Money look isn’t about breaking the bank.

It’s about investing wisely in enduring pieces that will make you look like a million bucks without spending it.

So, whether you’re a trust fund baby or a self-made man, stick with us, and we’ll have you strutting down the streets of London looking like you just stepped out of a Slim Aarons photograph.

Navy Blazer

If there’s one item that should be the cornerstone of your Old Money wardrobe, it’s a perfectly tailored, double-breasted navy blazer.

The blazer is a versatile piece that can take you from a day at the office to cocktails at the club, all while exuding an air of understated elegance.

Opt for a 100% wool blazer with brass buttons for a touch of nautical flair.

How to Style Your Navy Blazer

  • Pair with cream linen trousers and brown leather loafers for a summer soirée.
  • Dress it down with dark wash denim and a crisp white Oxford shirt for casual Fridays.
  • Layer over a cashmere turtleneck and grey flannel slacks for a sophisticated winter look.

White Dress Shirt

Old Money Wardrobe Essentials White Dress Shirt

No Old Money wardrobe is complete without a selection of impeccable white dress shirts.

Invest in a few high-quality, 100% cotton shirts with a spread collar and French cuffs.

Remember, the devil is in the details – make sure the fit is spot-on, and always opt for mother-of-pearl buttons.

Dress Shirt Do’s and Don’ts

  • Have your shirts tailored for a perfect fit.
  • Don’t wear shirts with frayed collars or cuffs.
  • Experiment with subtle patterns like micro-checks or hairline stripes.
  • Don’t go for loud, bold prints that scream for attention.

Tailored Trousers

Old Money Style Dress Pants

A well-curated selection of tailored trousers is the foundation of any Old Money wardrobe.

For summer, stick to classic colors like navy, charcoal grey, and khaki.

For fabrics, you can’t go wrong with lightweight wool, cotton gabardine, or linen.

Always opt for a slim, tailored fit with a slight break at the ankle.

Old Money Trouser by Occasion

  • Pair charcoal wool trousers with a light blue dress shirt, navy blazer, burgundy tie, and black cap-toe Oxfords – best for a business meeting.
  • Dress khaki cotton chinos up with a blue Oxford shirt, brown suede loafers, and navy cotton blazer – best for a weekend brunch.
  • Pair cream linen trousers with a navy dinner jacket, white dress shirt, black silk bow tie, and black patent leather loafers – best for an evening event.

Polo Shirts

Polo shirt

Nothing beats a classic Preppy-style polo shirt for a more relaxed Old Money look.

Choose polos made from high-quality cotton pique or lightweight merino wool.

Stick to timeless colors like navy, white, and pale blue.

The fit should be slim but not tight, with the sleeve hitting mid-bicep and the hem falling just below the waistband of your trousers.

Polo Shirt Styling Tips

  • Pair a navy polo with stone-colored chinos and brown suede boat shoes for a preppy summer look.
  • Layer a light grey merino wool polo under a navy blazer with dark wash jeans for a smart casual outfit.
  • Tuck a white polo into cream linen trousers and add a brown leather belt for a refined resort look.

Cashmere Sweater

Turtleneck Sweater

A soft, sumptuous cashmere sweater is an Old Money wardrobe essential for cooler months.

Invest in a few classic styles, such as a V-neck, crewneck, and turtleneck, in neutral shades like camel, navy, and light grey.

These versatile pieces can be dressed up or down, making them a go-to for any occasion.

Cashmere Sweater Styling Ideas

  • Layer a camel V-neck sweater over a white dress shirt with charcoal wool trousers for a polished business casual look.
  • Pair a navy crewneck sweater with khaki chinos and brown leather Chelsea boots for a smart weekend outfit.
  • Wear a light grey turtleneck under a navy blazer with cream linen trousers for a sophisticated evening ensemble.

Dress Shoes

Brogue Shoes

No Old Money wardrobe is complete without a curated selection of high-quality leather dress shoes. The essential styles every gentleman should own include:

  • Black cap-toe Oxfords for formal occasions.
  • Brown penny loafers for a preppy, casual look.
  • Dark brown suede desert boots for a smart casual option.
  • Brown leather double monk straps for a refined business casual look.

Classic Accessories

Old Money style accessories

When it comes to Old Money style, less is more. Choose accessories that are classic, subtle, and high-quality.

Accessory Recommendations
Watch A classic stainless steel dress watch with a leather strap, like a Cartier Tank or Jaeger-LeCoultre Reverso
Belt A simple, high-quality leather belt in brown or black with a subtle gold or silver buckle
Cufflinks Understated gold or silver cufflinks with a classic design, like knots or discs
Pocket Square A silk pocket square in a subtle pattern or solid color, neatly folded in a square or puff
Tie Classic silk ties in timeless patterns like stripes, dots, or paisley in muted colors

Styling Tips

Now that you’ve got the essential pieces, it’s time to combine them into cohesive, stylish outfits.

Outfit Formula Example
Blazer + Dress Shirt + Tailored Trousers + Oxfords Navy blazer, white dress shirt, charcoal wool trousers, black cap-toe Oxfords
Polo Shirt + Chinos + Loafers Light blue polo shirt, stone-colored chinos, brown penny loafers
Cashmere Sweater + Button-Down Shirt + Trousers + Boots Camel V-neck cashmere sweater, light blue Oxford shirt, khaki chinos, brown suede Chelsea boots

Remember, the key to nailing the Old Money look is to keep things classic, understated, and high-quality.

Avoid flashy logos, trendy pieces, and anything that feels too try-hard.

The goal is to look effortlessly elegant like you were born into a world of impeccable taste and style.

Your Old Money Style with The VOU

Gentlemen, if you’re ready to take your Old Money style to the next level, look no further than The VOU’s styling services.

Our team of expert stylists, myself included, are here to guide you on your journey to sartorial excellence.

We’ll work with you one-on-one to curate a timeless wardrobe that reflects your unique personality and lifestyle while staying true to the principles of Old Money dressing.

From perfectly tailored suits to casual weekend looks, we’ll ensure you always look and feel your best.

But The VOU’s services go beyond just looking good—we’re here to help you embody the confidence, sophistication, and joie de vivre that come with mastering the art of dressing well.

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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