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All answers having "Headgear" as clue:

3 Character Answers:

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CAP

FEZ

HAT

TAM



4 Character Answers:

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CAPS

HATS

HOOD

TAMS



5 Character Answers:

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BERET

COWLS

TOQUE



6 Character Answers:

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BERETS

CROWNS

HELMET

PANAMA

TITFER

TOPHAT



7 Character Answers:

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BONNETS

FLATCAP

PANAMAS

RAINHAT

TURBANS



8 Character Answers:

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OPERAHAT



9 Character Answers:

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COWBOYHAT

PANAMAHAT

SKULLCAPS



10 Character Answers:

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PORKPIEHAT

SUNBONNETS



11 Character Answers:

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MORTARBOARD