Old Money Shirts For Men: Top-Recommend Brands & Outfit Tips

This guide dives deep into the world of old-money shirts for men. We’ll explore the key characteristics that define this look, recommend some top brands known for their heritage and quality, and provide outfit tips to help you achieve that timeless elegance.

What Style Are Old Money Shirts For Men Called?

Actually, there isn’t a single, unique style designation for men’s “old money” shirts. More crucial is the general impression and appearance they provide. These shirts are the way to express “effortless elegance” in terms of apparel. These are timeless styles, excellent tailoring, and premium materials.

Shirts of the “old money” category include t-shirts, polos, and formal shirts, among other styles, but they all have certain things in common.

That’s why you can recognize them by their quality-focused design, neutral color palette, and straightforward lines—even if you won’t always see a brand labeling them “old money” shirts.

3 Old Money Dress Shirts Brands For Men

For males, these are three brands of the best old-money vibes:

Brooks Brothers

When it comes to old money aesthetics, few brands embody the spirit quite like Brooks Brothers. Founded in 1818, it’s the oldest apparel retailer in the United States, boasting a rich heritage of supplying presidents, CEOs, and style icons for generations.

Brooks Brothers use only the best cotton, linens, and even wool for their shirts. These fabrics breathe well, feel luxurious against the skin, and age gracefully over time. You won’t find flimsy or trendy fabrics here, but rather enduring materials built to last.

Owning a Brooks Brothers shirt is like owning a piece of American history. When you wear one, you’re not just wearing a garment; you’re carrying on a legacy of refined menswear. This subtle association with heritage adds a touch of understated sophistication to your old-money aesthetic.

Brioni

For the discerning gentleman seeking the pinnacle of old money style, Brioni stands as a crown jewel. This Italian powerhouse, established in 1945, isn’t just another shirt brand; it’s a symbol of sartorial heritage and unparalleled craftsmanship.

Back in the 1950s, they spearheaded the “Peacock Revolution,” introducing a new wave of menswear that embraced lighter fabrics, bolder colors, and a more fitted silhouette. This rebellious spirit, while introducing a touch of modern flair, never strayed from the core principles of old-money elegance.

Their shirts are crafted from the finest Egyptian cotton, exquisite silks, and luxurious linens. These fabrics are not only incredibly soft and breathable, but they also age beautifully, developing a unique character with each wear.

When you wear a Brioni shirt, you’re not only enjoying the best comfort and quality but also joining a tradition of old-money style that lasts longer than fashion trends.

Mr Porter

Unlike a department store, Mr Porter offers a carefully edited selection of shirting options. They focus on brands known for their heritage and commitment to quality, like Brooks Brothers. This ensures you get shirts embodying the old-money principles of classic cuts and luxurious materials.

While Mr Porter excels in classic dress shirts, they cater to the complete old-money wardrobe. You’ll find a curated selection of polos, t-shirts, and knitwear, all crafted from high-quality materials and designed to be mixed and matched for effortless sophistication.

What Brand Custom Vintage Old Money Shirts To Men?

Tired of off-the-rack shirts that never quite fit right? It’s time to remove the pain and update your wardrobe with men’s bespoke dress shirts from Hockerty.

Hockerty gives you the ability to create personalized apparel. Design your made-to-measure shirt online, selecting from a variety of materials and designs to create a standout item for any occasion.

Their expert tailors create the ideal dress shirt, skillfully combining comfort and refinement using the best fabrics and state-of-the-art techniques.

How To Wear Shirt Like An Old Money?

Old money shirts for men built around classic clothes, which you’ll need to fully nail this style. In this in-depth guide, we’ll talk about what each of these clothing essentials means:

Choosing the right shirts:

• Material: Focus on high-quality fabrics like breathable cotton, crisp linen, or luxurious cashmere.

• Color: Opt for neutral colors like white, light blue, light grey, and beige. These offer versatility and a timeless look.

• Fit: A well-fitting shirt should sit comfortably on your shoulders and arms, with a clean silhouette that flatters your body type. Invest in tailoring if needed.

Continue reading to learn how to put together outfits with old money shirts for men.

 Wearing A Men’s Shirt With A T-shirt To Look Like Old Money

To start with, the t-shirt. Think quality over quantity here. This is something a little more solid. Everlane creates amazing essentials; my recommendation is the organic cotton crewnecks. Beautifully draped and wonderfully comfy, the heavyweight cotton. Its consideration of sustainability will also make you feel good.

For work or a slightly dressier weekend outing, a classic Oxford cloth shirt from a brand like Brooks Brothers will never disappoint you. The breathable cotton keeps you cool, and the clean lines add a touch of formality. Choose crisp white or a subtle light blue – these colors work seamlessly with any t-shirt.

Choose pants in Khaki, olive green, or navy. Dark wash jeans, especially with the polo option, can also work for a more casual look.

Don’t forget that loafers or boat shoes are the epitome of the old money style. They add a touch of polish without being overly formal. Sneakers can also work, but keep them clean and simple.

Trying To Look Like Old Money With A Polo Shirt

Forget the flimsy, itchy polos you wore in high school. We’re talking about quality here. My personal favorite brand for polos that scream old money is Ralph Lauren.

Their classic fit polos are made from pique cotton, which offers a slightly textured look and superior breathability. Plus, the fit is spot on – not too baggy, not too tight, just right to flatter your physique.

Now, for the color palette. Navy and beige are your best bets. These neutral tones go with everything and never go out of style. White is also an option, but keep the button down (gasp!) for a more relaxed vibe, and wear a crewneck t-shirt underneath for a layered look.

Wearing chinos is like having a best buddy in trousers. Navy, khaki, or olive green are all great options. When opting for dark wash jeans for a more informal occasion, ensure they fit properly and avoid any distressing.

This polo shirt ensemble is perfect for weekend brunches, casual dates, or even dressier settings with the right blazer. It’s a versatile look that transitions seamlessly from day to night.

How To Combine Sweater, Cardigan, And Sweatshirt Like A Rich Gentleman? 

For sweaters:

Brands like Brunello Cucinelli or Loro Piana offer luxurious options that feel like a hug from a cloud. For a more traditional style, consider crewnecks; for something more modern, consider V-necks (Skip the overly baggy styles, they’re more “dad” than “don”.)

Perfect for fall and winter, or for layering in air-conditioned environments. Dress it up with chinos and loafers for a business casual look, or keep it cozy with jeans and boots for a weekend outing.

For a cardigan:

Opt for a fine merino wool cardigan from J.Crew for a versatile option you can throw over a dress shirt or a t-shirt. Think clean lines and a well-tailored fit – a boxy cardigan will just drown you.

This can be your workhorse! Layer it over a dress shirt for the office, or throw it on over a t-shirt for a casual yet put-together look on the weekend.

For sweatshirts:

This one can be tricky for old money style, but it’s not entirely out of the question. Think of a heavyweight, well-made sweatshirt in a neutral color like navy or grey. Everlane offers some great basics that are more polished than your average gym hoodie.

This is the most relaxed choice you have. You can do things like run errands on the weekend or watch the game with friends. But remember that a simple, well-made hoodie can go a long way.

Keep it simple. A timeless watch and maybe a simple chain necklace are all you need. If you’re feeling bold, a patterned pocket square in a muted tone can add a touch of personality.

Following the advice of Old Money Vibe 24h, we’ve shown you how to put together a men’s Old Money shirt wardrobe. Stay tuned to our site for additional advice on how to look like a million bucks.

Read more: Old Money Outfit Color Combinations For Men And Women.