14 best Old money hats and caps

These men wear formal old money outfits. Both wear a suit consisting of the colors blue and white. Also, they wear matching ties. One wears a hat and the other one sunglasses.

The first picture I had in mind as I heard of the term „old money“ was a woman at horse tracks dressed in the finest clothes and extraordinary old money hats. As I‘ve learned a little more, I still find this image of old money hats very interesting. So why not dedicate an article to look at the refined and noble world of old money hats?

This article will offer a comprehensive view of the history of old money hats and why they are worn in the first place. Additionally, we will look at a lot of specific types of hats and caps and their iconic brands. So, let’s jump right into this unique topic.

History of old money hats

Whilst some hats started as practical workwear and sun or rain protection in the construction field, they soon shifted to elegant accessories. 

Most of the featured hats in this list emerged during the late 1800s to the early 20th Century. Typically used to express a sophisticated appearance and the abstinence from physical labor, they were truly a fashion staple back then.

As these affluent people wanted to add some personal touch to their usually rather boring style, various hats suddenly witnessed multiple changes and adaptations to stand apart. 

Since most of these old money hats like the fedora or fascinate have been solely used for formal outings and to this day still are, owning one of those refined pieces of craftsmanship is an achievement on its own. Set aside the ability to wear it correctly.

Old money hats men

To start off, we will look at the male side first.

Top hat

Here, you can see a top hat, one of the most famous old money hats.
Via

Originating in the 19th century, the top hat, also called the cylinder hat, is a formal fashion staple renowned for its durability and versatility. Mostly worn by affluent individuals in the 19th and 20th centuries, this hat resembles a classic old money style nowadays.

Brands to shop it at:

  • Lock & Co. Hatters (£595)
  • Christys’ London (£195)

Bowler hat

Having the same English background and coming from a similar time, the bowler hat reminds me a lot of the top hat besides being a little less high. Perfectly suitable for a formal occasion requiring a suit or blazer, this old money hat is a unique fashion staple.

Brands to shop it at:

  • Bailey of Hollywood ($155)
  • Christys’ London (£105)

Homburg hat

This picture shows a man wearing a homburg hat.

This refined accessory with a distinctive crease along the crown has its origin in the late 19th century in the German town of Bad Homburg giving it its name. Being associated with nobility and elegance, especially between 1920-1930, this hat makes a great appearance in old money‘s wardrobe.

Brands to shop it at:

  • Christy‘s London (£220)
  • Borsalino ($370)

Deerstalker hat

A weird name for a hat, don’t you think? This uniquely designed hat originated in the United Kingdom as a useful Gadget for, the name may give it away, hunting. With its hinged side flaps that can either be fastened at the top of the crown or worn over the ears protecting them from the cold. This accessory, also featured in the famous series Sherlock Holmes represents old money and their activities perfectly.

If you want to know more about old money activities, check out my article about all of them here.

Brands to shop the Deerstalker hat at:

  • Lock & Co. Official (£215,40)
  • Failsworth hats (£50)

Old money hats for both genders 

Even though most hats will be seen by one gender primarily, there are some that work for both men and women.

Boater hat

The boater hat originated in the late 19th century in the United Kingdom as a lightweight headwear made from straw. Originally donned during leisurely activities on boats, this refined accessory became synonymous with wealth and quickly found its place in the United States, where it rapidly evolved into a fashion staple in the early 20th century.

Brands to shop it at:

  • Belfry hats ($149)
  • Stetson ($100)

Beanie

The classic beanie, a timeless fashion staple with the purpose of keeping your head and ears warm, is not particularly an old money hat yet it is worn by quite luxury because of its versatility and usefulness. Held in neutral colors, you can easily implement this accessory into your old money winter outfits.

To get to know more about old money winter outfits, check out this article.

Brands to shop it at:

  • Brixton ($25)
  • Tommy Hilfiger ($30)

Beret

Here, you can see a man and woman both wearing a beret but styling it differently. Both represent quiet wealth.

This flat crowned hat boasts a rich and versatile heritage, drawing inspiration from ancient Greece and the Basque region. It gained significant popularity in France and is primarily categorized into two main types: the French Beret and the Basque Beret. Even worn by the military, it resembles nobility and timelessness. 

Brands to shop it at:

  • Brixton ($35)
  • Kangol ($30)

Fedoras

The Fedora, a hat with a creased crown, suits both men and women perfectly. It originated during the late 19thcentury as a result of a French play called “Fédora”. Nowadays, this unique piece of headwear complements casual and formal outfits for men and women. Best held in neutral colors like black, brown, or gray, this old money hat will elevate any outfit.

Brands to shop it at:

  • Stetson ($200)
  • Baileý of Hollywood ($500)

Old money hats for women

Following the understated headwear styles, women’s “old money” hats offer a more vibrant and playful alternative, introducing a burst of color and lively designs.

Wide-brimmed fascinator hats

Wide-brimmed fascinator hats are the highlights of a classy women’s formal closet. The fascinator hat has been around since the 18th century and has always been reserved for the noble and royal people. Decorated with unique patterns, flowers, and feathers, these formal old money accessories can be found mostly at horse tracks or costume or wedding parties nowadays.

Brands to shop it at:

  • Philip Treacy (Price at request)
  • Gina Foster Millinery ($110)

Pillbox hat

This picture shows a pillbox hat in a petrol shade. A unique hat.

Even though the origin of the Pillbox hat dates to ancient times, its popularity just rose in the mid-20th century due to prominent influences. Worn by First Lady Jacqueline Kennedy, the pillbox hat is often regarded as a key element that defines classic fashion and remains a timeless accessory for those who appreciate elegant style.

Brands to shop it at:

  • Lock & Co. Hatters (£825)
  • Gina Foster Millinery ($165)

Cloche hat

This picture shows a cloche hat. It's coloured green and has a little flower at the side.

This unique creation stems from the French word for bell, which more or less describes its overall look. Worn mostly during the 1920s, this hat resembles understated elegance and sophistication all at once. Try to pair this unique accessory with an elegant dress or another formal old money outfit.

Brands to shop it at:

  • Scala ($70)
  • San Diego hat company ($45)

Old money caps

Although they are relatively contemporary in style, certain elegant caps can effortlessly embody the timeless appeal of old money fashion. Let’s look at some examples of old money caps:

Ralph Lauren ball caps

Here, you can see an old money cap by Ralph Lauren sitting in the store.
This picture shows a variety of old money caps from Ralph Lauren in store.

Made out of 100% cotton, Ralph Lauren Ball Caps embody a timeless yet stylish aesthetic. Due to their plain, unicolored designs and the small embroidered logo, these caps make up the perfect headwear for a casual old money outfit.

At a reasonable price of about $50-60 at their stores, you can get yourself a nice cap pretty easily. If you want to shop for them cheaper, thrift stores and outlets will be a perfect opportunity to do so. Due to their high quality, these caps will not wear out easily.

For a little more playfulness, choose their designs with the bear or checks and polo players. 

Loro Piana baseball cap 

You want to have an elegant cap costing more than most people’s outfits? Look no further: Loro Piana has you covered. Made out of high-quality wool or cashmere, baseball caps from Loro Piana offer a perfect fit as well as a timeless and elegant appeal, even though you “just wear” a baseball cap.

Priced in the range of $500 to $650, these caps are intended for the most financially well-off individuals. A cap featuring subtle checks will epitomize the old money style most effectively.

Tennis caps

A trendier and more affordable option lies in tennis caps. These can either come as just visors or a whole cap. Regardless of their form, these caps will feature embroidery of the club’s name and logo. Due to Tennis being an activity for rather affluent individuals, a logo or name of their club can represent old money pretty well.

If you don’t happen to be in a tennis club, you may surely find some affordable alternatives online. 

Final thoughts on old money hats

Even though they might not be the trendiest option right now, a timeless old money hat or cap can elevate a well-formed easily. Being made from professional hatmakers, these hats will resemble elegance and sophistication.

So go ahead, embrace your personal style by implementing a classy cap or hat from time to time.

FAQ

What is the best vintage old money hat?

If you’re opting for the number 1 best old money hat, the fedora is the right choice to make. Versatile, elegant, and timeless, you can wear this hat for almost any outfit.

What are the best old money hat brands?

The 2 best brands to shop old money hats at are Lock & Co. Hatters and Borsalino. You can find almost any of the above-featured hats at one of those brands.

Which rules apply to wearing an old money hat?

Consider the occasion, the level of formality, your overall outfit appearance, and the fit, and match it to your personal style.

Why are old money hats so expensive?

High-quality materials, extraordinary craftsmanship, traditional processes, exclusivity, and time-consuming detailing make a good old money hat quite costly.

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