Boo Wilbury
Inside Out video




A straw boater is a stiff straw hat with a flat top, a brim, and traditionally decorated with Petersham ribbon. The ribbons once signified allegiance to a particular educational institution or sailing club. 

Legend has it that these hats were brought to the USA by Italian immigrants and named 'boaters' because they were worn by Venetian gondoliers. However, they were also popular in England as summer headgear, especially for rowing and punting activities, from the late 19th Century onwards. 

Bob's hat in 1990 had a dark navy and red trim. It is more likely to be an authentic early style boater with no significance to the ribbon colours. 



'Unbelievable' promo video
Wearing a chauffeur's uniform hat
Mojave Dessert
Under The Red Sky




Internationales Congress Centrum
Berlin, Germany
July 1990



The hat is a genuine ushanka this time - with the earflaps tied up and a badge on the brim. An interesting choice of headgear to wear in Berlin during the year the wall came down.

This hat made other appearances. Here it is in use at the Beacon Theatre, New York , 15 October 1990.



Beacon Theatre
New York City, New York
Photo by John Hume


Here, Bob Dylan is wearing a brown fedora



Fox Theatre
St. Louis, Missouri


Under The Red Sky.

Similar hat to that worn at the Grammy presentation, February 1991 (below). 



Travelling Wilburys Promo photograph
White baseball cap worn backwards! 

Recording sessions were a year earlier:




Grammys Lifetime Achievement Award

"Well, my daddy, he didn't leave me much, you know he was a very simple man, but what he did tell me was this, he did say, son, he said…" [Nervous laughter from the crowd] "…he said, you know it's possible to become so defiled in this world that your own father and mother will abandon you and if that happens, God will always believe in your ability to mend your ways."






In 1991 an 'interview' with Bob Dylan was published in The Telegraph (issue 42). It was supposedly conducted by journalist and translator Eduardo Bueno in Budapest on 12 June 1991. 

The interview was a fake. Bueno had compiled a selection of previous Bob Dylan responses from other interviews. 

One extract from the 'interview' was about hats

 EB: On your 50th birthday, an English newspaper, The Independent, asked a lot of people what they'd give you as a birthday present. Mick Jagger said, After what I saw on the Grammys, a new hat and some good songs.

BD: Well, a new hat I've already got. It's here. It's called a Borsalino. I bought it in Milan, five days ago, for $75. New songs? Well, I don't think he's ever written a song like Masters of War. But to do my show, I don't need to be moving from here and there. But I love Mick, I always did. 

Read the entire story and 'interview' here


Late 1991

LA Times photo 
Uncredited and undated.
Bob Dylan wearing a bandana. 



Australia tour, 1992
Brooklyn baseball cap under hoodie - and carrying a didgeridoo. 




Bill Clinton’s Inauguration Concert




Camden Lock Market. London
Blood in My Eyes video shoot
Photos by Anna Marie Velez

World Gone Wrong album recorded in May 1993:



   HAT FACT... 

Dave Stewart directed the video for 'Blood In My Eyes'. It was filmed at Camden Lock Market, London, on July 21st 1993 and featured Bob Dylan walking around, juggling, talking to passers-by and signing autographs. 

On Dave Stewart's website, he displays the result with the following caption:

“Below is a video I directed with Bob Dylan using 8mm one morn in London. I hired a top hat. It was our only prop!” 

It is hoped that Bob Dylan's appearance that day, while exciting enough for passers-by, did not cause the 'Menace to Society' that the first appearance of a top hat in London instigated 196 years earlier:

"According to The American Hatter, London haberdasher John Hetherington nearly caused a riot when he wore the first top hat into the Strand on Jan. 15, 1797:

An excited throng gathered about the owner and the crowd soon increased to such a dangerous extent that the authorities had to interfere. The next morning the daring haberdasher was brought before the Lord Mayor charged with ‘walking down a public highway wearing upon his head a tall structure having a shining lustre calculated to alarm the people.’

Witnesses testified that “women had fainted, that children had gone into hysterics and that one lad sustained a broken arm through the violence of the mob.” Hetherington asserted his right to dress as he chose, but the Lord Mayor fined him $5,000."



Memorial Stadium
Seattle, Washington
21 August 1993

Interview with Carlos Santana 
For MTV 



Shin-Osaka Station, Japan.

What kind of a hat is this? A tweed golfer's hat or 'newsboy cap' worn peak-backwards?



July [?] 1994

This is a photograph of Bob Dylan meeting Rabbi David Pinto, reportedly in Paris during the European leg of his 1994 tour.


You can read about the meeting here

Bob is pictured wearing a traditional Jewish kippah (כִּיפָּה) which is also known as a yarmulke. This is a round skull-cap usually made of cloth that fulfills the customary requirement that the head should be covered at all times. 


Summer 1996

 Photographed by Sam Erikson in Germany during the summer tour of 1996.

Bob Dylan and Dave Matthews

Grosses Zelt
Klein Venedig
Konstanz, Germany
3 July 1996


The style of hat worn by Bob Dylan here is a variation on a top hat. It is sometimes referred to as a 'coachman's hat' or Junior Top - with a flat crown, not as tall as a traditional top hat, and a curved brim.

The style has since become popular with Steampunk costume designers. Another first in the field? ;-) 



Beale Street Festival
Tom Lee Stage, Tom Lee Park




Grammy Awards
Radio City Music Hall, New York
Pictured with Tommy Mottola




Bob Carpenter Centre, Newark, Delaware
US Fall Tour with Phil Lesh and Friends



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