The most common and most likely answer to this crossword clue is the 7 plus 4 letter word PORKPIE HATS
P
O
R
K
P
I
E
H
A
T
S
Buddy explains!
The straight part
We know that "I/tems of headgear" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case i/tems of headgear = porkpie hats.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.