Vintage and Antique Hats

64 Vintage and Antique Hats For Sale

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There was a time when no man or lady would dream of leaving their house without a hat. Like a good pair of gloves or a smart tie, no respectable person would omit this vital piece of clothing that over the years changed styles numerous times to reflect the tastes and fashions of the era. Fast forward to recent decades, and hats became a way to express affiliation with sports clubs, brands, and were bought as souvenirs.

Nowadays, hats of all kinds are incorporated into our day to day looks to match our own unique tastes and style and a vintage or antique piece of millinery can be the perfect accessory to express who you are.

In this article we’ll be exploring the various types of vintage and antique hats which are for sale online as well as some tips and tricks for how to pick your perfect item.

Are Vintage Hats Worth Anything?

Like with all things, some are and some aren’t. Fashions come and go, so the value of a vintage piece of headwear will shift with the trends. Like with jewlery, many hats designed by professional milliners come with their own makers mark. This provenance can appeal to collectors and increase the value of an item. Most surprisingly valuable, however, are retro trucker caps and baseball caps. Most valuable are items which commemorate historical events or old branding such as Nasa caps and Disney caps, as well as those which depict popular characters.

Our Favourite Vintage and Antique Hats

Listed below is our curated list of some of the most exciting examples of vintage and antique hats currently for sale. We’ve split our list into various categories and eras to help you find what you’re looking for.

I) Vintage Caps

1. Vtg Greek Fisherman’s Cap

Condition (New/Used): Good Condition / Used
Color: Black
Size(s): 8
Price: $30.00


Buy this hat here.


2. Vintage WWII US Army Winter Hat Small Duck Cotton~Wool Cold Weather Cap

Condition (New/Used): Good Condition / Used
Color: Cream
Size(s): Small
Price: $72.00


Vintage WWII US Army Winter Hat Small Duck Cotton~Wool Cold Weather Cap

Buy this hat here.


3. Vintage Tweed Cap – Herringbone Check Wool – Newsboy Flat Cap – Country Classic Hat-unisex- Driving cap – Small 21″- 53cm -6 3/4-

Condition (New/Used): Good Condition / Used
Color: Dark Red/Green/Black/Blue/Light Brown
Size(s): Small
Price: $35.76


Vintage Tweed Cap

Buy this hat here.


4. Vintage English tweed flat cap traditional flat cap wool check made in England Quality cap size S/M

Condition (New/Used): Good Condition / Used
Color: Dark Red/Green/Black/Blue/Light Brown
Size(s): Small/Medium
Price: $43.17


Vintage English tweed flat cap traditional flat cap wool check made in England

Buy this hat here.


5. Vintage Docker Cap Big logo Porter beer patch summer authentic retro unisex accessories embroidery front logo beanie hip hop brimless black

Condition (New/Used): Used
Color: Black
Size(s): Medium
Price: $24.00


Buy this hat here.


6. Vintage 50s 60s Flat Cap Brown Tweed & Suede Small

Condition (New/Used): Used
Color: brown/grey/creme
Size(s): 7⅛
Price: $25.20


Buy this hat here.


7. Vintage dark green wool and tan suede bill flat cap London Fog label made in USA Newsboy Andy Capp Peaky Blinders khaki lined flat cap Sz L

Condition (New/Used): Used
Color: Dark Green
Size(s): 7¼ – 7⅜
Price: $33.60


Buy this hat here.


8. Vintage 60s Kangol Wool Mocha Rolled Brim Winter Cap

Condition (New/Used): Conduction is used with some moth holes throughout (pictured)
Color: Cream
Size(s): Inner Head Circumference 21”
Price: $38.40


Vintage 60s Kangol Wool Mocha Rolled Brim Winter Cap

Buy this hat here.


II) Vintage Trucker Hats

1. 80’s vintage trucker-style hat.

Condition (New/Used): Wore Condiction with “some cracks”
Color: Blue
Size(s): One Size fits all
Price: $38.40


Buy this hat here.


2. Vintage 80s 90s North End Fire Company 3 Stripe Mesh Trucker Hat Snapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: White/Yellow/Red
Size(s): One Size fits all
Price: $30.00


Vintage 80s 90s North End Fire Company 3 Stripe Mesh Trucker Hat Snapback Hat Baseball Cap

Buy this hat here.


3. Vintage 80s 90s Camo Eastern Shore Sportsman’s Paradise Mesh Trucker Hat Snapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condiction
Color: Eastern Camo
Size(s): One Size Fits All
Price: $30.00


Buy this hat here.


4. Vintage 80s 90s California Raisins Mesh Trucker Hat Snapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condiction
Color: White/Black
Size(s): One Size Fits All
Price: $66.00


Vintage 80s 90s California Raisins Mesh Trucker Hat Snapback Hat Baseball Cap

Buy this hat here.


5. Vintage 80’s NASA Embroidered Gold Logo Black Snapback Trucker Mesh Hat Cap

Condition (New/Used): Great Vintage Condition
Color: Black/Yellow
Size(s): One Size Fits All
Price: $23.94


Vintage 80's NASA Embroidered Gold Logo Black Snapback Trucker Mesh Hat Cap

Buy this hat here.


III) Vintage Baseball Caps

1. Vintage 90s Minimal Unstructured Big River Guns Ammo Bait Tackle Strapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: Dark Blue/Yellow
Size(s): Adjustable
Price: $30.00


Vintage 90s Minimal Unstructured Big River Guns Ammo Bait Tackle Strapback Hat Baseball Cap

Buy this hat here.


2. Vintage Miami Beach Florida Hat Miami Stitch Low Profile Unstructured Strapback Hat Baseball Cap

Condition (New/Used): Excellent
Color: White
Size(s): Adjustable, One size fits all
Price: $36.42


Vintage Miami Beach Florida Hat Miami Stitch Low Profile Unstructured Strapback Hat Baseball Cap

Buy this hat here.


3. TORONTO RAPTORS Starter fitted 1995 vintage hat 90s hat cap size 7- 7 3/4 Stretch

Condition (New/Used): New
Color: Black
Size(s): 7¾ with Strap
Price: $30.60


TORONTO RAPTORS Starter fitted 1995

Buy this hat here.


4. Anaheim Mighty Ducks Cap (Vintage)

Condition (New/Used): New
Color: Khaki/Dark Blue
Size(s): One Size Fits All
Price: $35.37


Anaheim Mighty Ducks Cap

Buy this hat here.


5. San Jose Sharks Cap (Vintage)

Condition (New/Used): Brand New
Color: White
Size(s): One Size Fits All
Price: $36.37


Buy this hat here.


6. Vintage 90s Minimal Broadway Comics Strapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: Black
Size(s): Adjustable
Price: $33.60


Buy this hat here.


7. Vintage Disney 2001 Strapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: Black
Size(s): Adjustable
Price: $42.00


Vintage Disney 2001 Strapback Hat Baseball Cap

Buy this hat here.


8. Vintage Barnes Concrete Strapback Hat Baseball Cap

Condition (New/Used): Good Vintage Condition
Color: Maroon
Size(s): Adjustable
Price: $24.00


Vintage Barnes Concrete Strapback Hat Baseball Cap

Buy this hat here.


9. Vintage 90s Safe Chimney Fire Strapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: Black/Red Flames
Size(s): Adjustable
Price: $30.00


Vintage 90s Safe Chimney Fire Strapback Hat Baseball Cap

Buy this hat here.


IV) Vintage hats for men

(1920s to 1940s)

1. French antique Felt bowler hat/Derby hat. Excellent condition. Without wear or damage. (1120T)

Condition (New/Used): Excellent Condition
Color: Black
Size(s): 55 cm (21.75 inches)
Price: $113.96


French antique Felt bowler hat

Buy this hat here.


2. Antique 1920’s “Great Gatsby” Black Silk Collapsible Top Hat

Condition (New/Used): Used with little marks
Color: Black
Size(s): Height: 5 Inches/Length: 11 1/4 Inches/Width: 9 1/2 Inches/Inside Rim Diameter: 22 Inches
Price: $78.00


Antique 1920’s “Great Gatsby” Black Silk Collapsible Top Hat

Buy this hat here.


3. 1920s-30s Billy Boy Tam Cap – black wool felt – boys, XS men – vintage men’s hat

Condition (New/Used): Good Antique Condition
Color: Black
Size(s): Circumference 21″
Price: $28.80


1920s-30s Billy Boy Tam Cap

Buy this hat here.


4. Borsalino Pocket Hat 1940’s-1950’s

Condition (New/Used): Perfect Condition
Color: Brown
Size(s): 7 (5 is the italian size)
Price: $299.99


Borsalino Pocket Hat

Buy this hat here.


5. Vintage Richman Brothers ‘Richcraft’ felt hat

Condition (New/Used): Great Vintage Condition
Color: Brown
Size(s): 56cm
Price: $50.36


Buy this hat here.


6. 1940s Handsome Homburg Hat | Vintage 40s Noir Black Fur Felt Men’s Fedora with Black Grosgrain Ribbon Band | Size 7&1/8 Medium

Condition (New/Used): Great Vintage Condition
Color: Black
Size(s): 7⅛
Price: $265.00


1940s Handsome Homburg Hat

Buy this hat here.


7. 1930s Stetson Summer Boater | Vintage 30s Pressed Woven Straw Hat with Black & White Striped Grosgrain Ribbon Bow Trim | Size 7 1/4 Large

Condition (New/Used): Great Vintage Condition
Color: Strew
Size(s):
Price: $245.00


1930s Stetson Summer Boater

Buy this hat here.


V) 1950s

1. FABULOUS Vintage 50s STEVENS FEDORA, Gray, 7 fits to 7 1/8th

Condition (New/Used): Worn Condition
Color: Pale Brown
Size(s): 7 – 7⅛
Price: $102.00


FABULOUS Vintage 50s STEVENS FEDORA

Buy this hat here.


2. Vintage Resistol size 7 Men’s Fedora Hat, 1950s Beaver Felt Dark Charcoal, Self Conforming Has Black Band Red Feather, with Orig Box!!

Condition (New/Used): Good Vintage Condition
Color: Black
Size(s): 7
Price: $114.00


Buy this hat here.


3. 50s Wool Houndstooth Trilby/ Dawson Park Ave/ Midcentury Men’s Hat

Condition (New/Used): Used
Color: Brown/Red/Green
Size(s): 8¾”
Price: $90.00


Buy this hat here.


VI) 1960s to 1980s

1. 1950s Style Porkpie Fedora | Vintage 80s does 50s Black Wool Felt Men’s Hat with Black Grosgrain Ribbon Band | Size 6 7/8 Small

Condition (New/Used): Great Vintage Condition
Color: Black
Size(s): 6⅞”
Price: $132.00


1950s Style Porkpie Fedora

Buy this hat here.


2. Vintage Men’s Fedora

Condition (New/Used): Excellent Condition
Color: Brown/Cream
Size(s): 23” Circumference
Price: $35.94


Buy this hat here.


3. Vintage Panama Men’s Sun Hat Sz M Raffia Straw Summer Tropical Print Band Mexico

Condition (New/Used): Used/Preowned Vintage Condition
Color: Cream
Size(s): Medium
Price: £32.39


Vintage Panama Men's Sun Hat Sz M Raffia Straw Summer Tropical Print Band Mexico

Buy this hat here.


4. Timeless 1960s Men Fedora PANAMA STRAW HAT ~ Handmade in Ecuador ~ Vintage New/Old Stock ~ L

Condition (New/Used): New Condition
Color: Cream
Size(s): large
Price: $84.00


Timeless 1960s Men Fedora PANAMA STRAW HAT

Buy this hat here.


5. 1960s Men’s Fedora Hat by Hush Puppies – Brown Pigskin Casual Headwear – Size 7 – Made in Ireland – Braided with Feather – Men’s Accessories

Condition (New/Used): Great Condition
Color: Brown
Size(s): 7⅛”
Price: $57.60


Buy this hat here.


VII) Vintage hats for women

1920s to 1940s

1. Vintage 1940s hat // face framing dark brown felt 40s hat // large asymmetric brim + rounded crown

Condition (New/Used): Good Condition with some marks
Color: Black
Size(s): 21.75″ Circumference
Price: $66.00


Vintage 1940s hat

Buy this hat here.


2. 1940s/1950s Black Hat Fascinator with Rhinestones

Condition (New/Used): Excellent Condition
Color: Black
Size(s): 19.75″ Circumference
Price: $38.40


1940s/1950s Black Hat Fascinator with Rhinestones

Buy this hat here.


3. 1920s Straw Hat | Lovely 20s Straw Hat with Silk Flowers | 1920s Cloche

Condition (New/Used): Very Good
Color: Straw Texture
Size(s): 21” Circumference
Price: $144.00


Buy this hat here.


4. Original Henry Pollak 1920s black cloche hat 100% wool skull cap felt flower decoration original labels inside

Condition (New/Used): Great Condition
Color: Dark Blue
Size(s): 59.5cm internal diameter approximately
Price: $79.14


Original Henry Pollak 1920s black cloche hat

Buy this hat here.


5. Vintage 1940’s Dark Brown Wool Tilt Hat / Feather

Condition (New/Used): Good Vintage Condition
Color: Dark Brown
Size(s): 10.5” Circumference
Price: $154.80


Vintage 1940's Dark Brown Wool Tilt Hat

Buy this hat here.


6. Vintage 1940s hat / 40s green cloche style fall winter hat one size fits most

Condition (New/Used): Excellent Condition
Color: Pale Green
Size(s): 22” Circumference
Price: $50.40


Buy this hat here.


VIII) 1950s

1. Vintage 1950s Black velvet hat, skull cap with black feather adornment

Condition (New/Used): Clean Condition
Color: Black
Size(s): 57cm Circumference
Price: $41.73


Vintage 1950s Black velvet hat

Buy this hat here.


2. Original Vintage 1940s/1950s Mustard Yellow Felt Pill Box Half Hat

Condition (New/Used): Excellent Condition
Color: Yellow
Size(s): 21¼” Circumference
Price: $64.75


Buy this hat here.


3. 1950s Vintage Miss Alice Velvet Ladies Hat

Condition (New/Used): Good Condition
Color: Pink
Size(s): 20 ½”
Price: $16.80


1950s Vintage Miss Alice Velvet Ladies Hat

Buy this hat here.


4. Vintage 1950s/50s Navy Blue Wool Felt Grosgrain Ribbon Fedora

Condition (New/Used): Great Condition
Color: Navy Blue
Size(s): 21” Circumference
Price: $81.60


Vintage 1950s/50s Navy Blue Wool Felt Grosgrain Ribbon Fedora

Buy this hat here.


5. Vintage 1950s Women’s Orange Fabric Head Band, Embroidered Daisy Adornments, Mid Century, Fall Fashions, Retro Hats, MCM Hair, Halloween

Condition (New/Used): Good Condition
Color: Orange
Size(s): No Size Given
Price: $24.00


Buy this hat here.


6. Vintage 1950s Velvet Hat / 50s retro tricolor mini pillbox style hat one size

Condition (New/Used): Excellent
Color: Blue
Size(s): One Size Fits All
Price: $50.40


Vintage 1950s Velvet Hat

Buy this hat here.


7. Vintage 1950’s Apricot Orange Tulle Platter Hat

Condition (New/Used): Excellent Vintage Condition
Color: Orange
Size(s): Fits Most Heads
Price: $117.60


Vintage 1950's Apricot Orange Tulle Platter Hat

Buy this hat here.


IX 1960s to 1980s

1. Vintage Cloche Hat. Made in Italy. Pure Wool. Flapper Hat. Felted Wool. Gray and Pink Bow. Like New. Will Fit Adult Woman.

Condition (New/Used): Excellent Condition
Color: Grey With Pink ribbon
Size(s): 22 ½” Circumference
Price: $34.74


Vintage Cloche Hat

Buy this hat here.


2. Men’s 60’s Vintage hat | Borsolino style hat | felted wool hat | grey wide-brimmed men’s hat | men’s fedora

Condition (New/Used): Worn Condition
Color: Dark Grey
Size(s): Circumference 54cm/Height of 12cm/Brim 6.5cm
Price: $56.81


Men's 60's Vintage hat

Buy this hat here.


3. Vintage 1960’s mohair bucket hat

Condition (New/Used): Good Vintage Condition
Color: Brown
Size(s): 53cm Circumference
Price: $37.41


Vintage 1960's mohair bucket hat

Buy this hat here.


4. Vintage Retro 1970’s Denim Newsboy Hat

Condition (New/Used): Worn
Color: Blue
Size(s): Size Fits a Range of Sizes
Price: $26.40


Vintage Retro 1970’s Denim Newsboy Hat

Buy this hat here.


5. Vintage French burnt orange wide-brimmed felt hat. Autumnal colors. 1960s-70s

Condition (New/Used): Excellent Condition
Color: Orange
Size(s): 54cm circumference
Price: $60.43


Vintage French burnt orange wide-brimmed felt hat

Buy this hat here.


6. Vintage 1970’s brown felt cloche hat

Condition (New/Used): Good Vintage Condition
Color: Brown
Size(s): 54cm Circumference
Price: $35.97


Buy this hat here.


7. Vintage 1970s/70s Orange Crochet Knit Floppy Brimmed Beret

Condition (New/Used): Very good condition
Color: Orange
Size(s): 12” Diameter
Price: $38.40


Buy this hat here.


8. Vintage 1970s navy blue straw hat

Condition (New/Used): Very Good Condition
Color: Navy Blue
Size(s): 38cm Diameter
Price: $46.95


Vintage 1970s navy blue straw hat

Buy this hat here.


X) Vintage hats snapback

1. Vintage Think Different Apple Mac Snapback Hat Cap

Condition (New/Used): New Condition
Color: Black
Size(s): One Size Fits All
Price: $24.99


Vintage Think Different Apple Mac Snapback Hat Cap

Buy this hat here.


2. Vintage 90s Indy 500 Racing Mesh Trucker Hat Snapback Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: Red
Size(s): One Size Fits All
Price: $42.00


Vintage 90s Indy 500 Racing Mesh Trucker Hat Snapback Baseball Cap

Buy this hat here.


3. Vintage 80s 90s Deadstock Super Mario Bros Mesh Trucker Hat Snapback Hat Baseball Cap

Condition (New/Used): Great Vintage Condition
Color: White
Size(s): One Size Fits All
Price: $210.00


Vintage 80s 90s Deadstock Super Mario Bros Mesh Trucker Hat Snapback Hat Baseball Cap

Buy this hat here.


4. Vintage 1988 Los Angeles Lakers NBA Champions Youngan Snapback hat cap rare 80s deadstock Magic johnson Kareem

Condition (New/Used): Excellent Condition
Color: White
Size(s): One Size Fits All
Price: $35.99


Vintage 1988 Los Angeles Lakers NBA Champions Youngan Snapback hat cap rare 80s deadstock Magic johnson Kareem

Buy this hat here.


5. Vintage 90s Pink Hawaiian Print Baseball Hat Blank

Condition (New/Used): Very Good Condition
Color: Pink
Size(s): One Size Fits All
Price: $14.40


Vintage 90s Pink Hawaiian Print Baseball Hat Blank

Buy this hat here.


Vintage Hat Styles

There’s been many changes to hat styles and designs over the years, and knowing the names of the different styles of hats can really help you to pin down the era or specific look you’re on the hunt for. Here’s a handy guide for both men and women:

Vintage Hats for Men

  • Top Hats: Top hats have long been a sign of refinement and are well-known for their usually black design and ribbon band. Created from stiffened calico, top hats came ina variety of heights and styles and some were even collapsible.
  • Bowler Hat: Commonly called the Derby hat in the USA, is a classic piece of headwear that came to define the quintiscessntial british gentleman. It was also the first mass produced hat in history. Charlie Chaplain is known for immortalizing the bowling hat in modern popculture. A later version of the Bowler hat is known as the Homburg Hat.
  • Boater Hat: The boater hat was the staple of a mans summer wear and are still worn in some private schools today. Made of stiffened sennet straw, the boater hat has a flat top and brim and is usually accented with a colored ribbon.
  • Fedora/Trilby Hat: The fedora was most popular in the USA, whilst the slightly smaller trilby gained more popularity in the UK. Both felt hat with dented crowns and turned up brims at the back, these hats graced the heads of movie stars, presidents, and even gangsters.
  • Panama Hat: The Panama has was a more modern rendition of the stiff boater hat and was made out of jipijapas straw, making the hat flexible enough to be rolled into a tube for transportation. These hats were made in Ecuador and shipped via the Panama canal; which is how these hats got their name.
  • Cloth Caps: Cloth caps have come in many different styles over the years from the flat cap, to the newsboy hat, and have dipped in and out of fashion since the Victorian era. Made from of a variety materials including tweed and wool, cloth caps of various kinds are still in mass production today.
  • Modern Hats/Caps/Truckers/Snapbacks: These hats rose to popularity with the rise in modern sports such as baseball and basketball. A great way for fans to show support for their team, this style of cap was also made popular by long-distance truck drivers who found the large brim perfect for keeping the sun out of their eyes.

Vintage Hats for Women

  • Edwardian Era: Hats were an absolute must for women in the early 20th century, and hats grew very large with sweeping brims which were intended to emphasise the slimness of the womans waist. Secured with pins, these large and ornate head pieces were often an uncomfortable fashion statement.
  • Cloche Hat (1920s): Cloche hats envelop the head like a cloche used at the dinner table.
  • Wide Brimmed Hats (1930s): To accommodate changing hairstyles, the 1930s saw the return of wide brimmed hats which had been popular in the Edwardian era. Woman also wore their own version of a man’s fedora, usually pinned in place at a jaunty angle.
  • The 1940s and 50s: This era saw an explosion in hat styles which suited the various fashions of Europe and the Americas. Many hats in this era experienced with shapes and staples and luncded feathers, veiling, and artificial flowers. The bonnet also saw a brief resurgence in this era.
  • Late 1950s: Hats were back to daily use for women and were deemed an essential fashion accessory in the 1950’s. Many women looked to the Hollywood starlets of the day for inspiration and hates such as the ‘pancake’ and ‘cartwheel’ hats became popular. Even the turban made an appearance during this time.
  • 1960s: The 1960s saw the emphasis return back to hairstyles with large styles such as the beehive making wearing hats nearly impossible.The most popular hat of this era, the Pillbox hat was made popular by Jackie Kenedy, and the first lady was even wearing one during her husbands assassination.
  • 1970s: The 1970s saw hairstyles relax again and hats also took on a relaxed style. The ‘newsboy’ hat popular with boys in the Victorian era became popular headwear for women as were wide brimmed hats and straw hats which suited the hippy aesthetic.
  • Modern Day: Hats have come in and out of vogue for women in modern years, with large wide brimmed hats having a recent resurgence alongside caps and bucket hats which suit the 90’s revival style.

Final Thoughts

While styles and trends may come and go your unique aesthetic is timeless. Hats can be a great way to express your uniqueness, and can also (in the case of trucker hats and caps) be an excellent nostalgic memento to collect. We hope our list has inspired you to investigate the fascinating world of headwear a little more.


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