Possible Questions:
- Monopoly token
- Shade provider
- Topper
- Chapeau
- Haberdashery item
- Magician's prop
- Head covering
- Panama
- Monopoly token choice
- Old ___
- Lid
- Derby
- Covering
- Santa wears one
- Bowler, for one
- Bowler, e.g.
- Something to check
- Beanie
- Panama, for one
- Beanie or beret
- It may be over your head
- It may be cocked
- Uncle Sam feature
- Part of a Santa costume
- Panama, e.g.
- Derby, e.g.
- This may be over your head
- Sombrero, e.g.
- Fez or fedora
- Derby, for one
- Something to tip
- Pillbox, e.g.
- Bowler
- Boater or bowler
- Sun protection
- Head cover
- Deerstalker, for one
- Stetson, e.g.
- Millinery sale
- Bowler or boater
- Tip from a gentleman?
- Part of an Uncle Sam costume
- Noodle topper
- It may be tipped
- It may be checked
- Fedora
- Cloche or toque
- Bowler or skimmer
- Boater, e.g.
- Uncle Sam costume piece
- Top ___
- Souvenir shop purchase
- Something to doff
- Milliner's product
- It may be passed
- Deerstalker, e.g.
- Beaver, for one
- Word with band or box
- Where a rabbit may be hidden
- Uniform part
- Toque, for one
- Stovepipe, e.g.
- Skimmer, e.g.
- Sailor, e.g.
- Ring toss item?
- Place for a band
- Pillbox, for one
- Pillbox or porkpie
- Pillbox
- Pate protector
- Panama or cowboy
- Millinery item
- Magician prop
- Kepi
- Item thrown in a ring
- It might go over your head
- Fez, e.g.
- Cloche
- Bonnet or beret
- Boater, for one
- Beret or bonnet
- Bad hair day helper
- ___ trick
- Word with box or trick
- Vocational identifier, perhaps
- Tuque
- Toque or cloche
- Thing to tip
- Stovepipe, for one
- Stovepipe
- Stetson, for one
- Stetson or sombrero
- Sombrero
- Rug covering
- Receiver of donations?
- Rack item
- Porkpie, e.g.
- Porkpie or pillbox
- Pork pie, e.g.
- Pillbox or toque
- Old or top
- Milliner's offering
- Magician's stock item
- Lincoln's was a stovepipe
- Item often checked
- Item for a bad hair day?
- It's passed for money
- It may be passed or tipped
- It may be passed or cocked
- It may be hard on a construction worker
- It may be filled with money or hair
- Hair hider
- Gibus or kady
- Fundraisers pass it
- Fedora or cloche
- Easter display
- Donation collection site
- Derby, for example
- Checkroom item
- Castor, e.g.
- Brass ___
- Bowler or porkpie
- Bowler or beret
- Billycock
- Beret, for instance
- Beret, for example
- Bean cover
- A milliner makes it
- "You Can Leave Your ___ On"
- "The Cat in the ___"
- "Poodle ___" ("Weird Al" Yankovic album)
- You may check it, although it's over your head
- Word with trick or tree
- Word with old or hard
- Word with high or top
- Word with hard or high
- Word with dance or band
- Word before box or trick
- Word after high or top
- Word after high or opera
- Word after hard or high
- Whence some rabbits
- What to keep a secret under
- What men doff to Key
- What Joe Cocker told you to leave on
- What a tipper tips
- What a gentleman tips
- Vocational identifier: sl.
- Used by street performer for tips
- Type of trick or rack
- Type of trick for a Ranger
- Trucker or bowler
- Trilby, e.g.
- Trilby on a Londoner
- Tricorne, e.g.
- Tricorn, for one
- Toque, e.g.
- Toque or tam
- Toque or porkpie
- Toque or gibus
- Toque or fez
- Toque
- Tipper's item
- Tipped top
- Tin Man's funnel accessory
- This might go over your head
- This clue's answer may be over your head
- Thing often checked
- The last word of this puzzle's five longest answers is a type of one
- The ____ (Southern Alberta city to some)
- Tam or bowler
- Tam or beret
- Tam or beanie
- Tam O' Shanter, or pork pie
- Symbol of a position
- Sunburn preventer, maybe
- Stovepipe for one
- Stetson or homburg
- Steeple-crown
- Sou'wester, e.g.
- Sometimes it's high
- Something to tip or check
- Something to hang on a tree
- Something to fling into a ring
- Something in a rack
- Sombrero, for example
- Solution for a bad hair day
- Shako or dicer
- Sartorial accent for Justin Timberlake
- Santa has a red and white one
- Sailor or skimmer
- Ring contents, maybe
- Remedy for a bad hair day
- Receiver of donations
- Rack type
- Prop for a magician
- Porkpie for one
- Porkpie
- Place for a rabbit in a magic act
- Place for a plume
- Passed item at a fundraiser
- Party handout, perhaps
- Part of Frosty's outfit
- Overhead item?
- Opera or hard
- One of multiple jobs, metaphorically
- One of many jobs, in metaphor
- One of 500 in a Seuss tale
- One might get tipped
- One may be in the ring
- One may be cocked
- On-the-rack item?
- Old _____
- Old ___ (passé)
- Nut covering
- Noodle topper?
- New Year's party handout
- New Year's Eve party handout, perhaps
- New Year's Eve party handout
- Milliner's ware
- Milliner's sale
- Mid-Manhattan
- Mexican-dance need
- Mexican ___ dance
- Medicine ___, Alberta
- Medicine _____
- Makeshift ballot holder, maybe
- Magician's item
- Magical item for Frosty the Snowman
- Kind of dance or trick
- Kind of dance or band
- Kind of check or rack
- Kind of box or band
- Keep-under item
- Kady or petasus
- Joe Cocker can leave his on
- Job, figuratively, and what's inside each of this puzzle's four longest entries
- Jipijapa, e.g.
- Item with a brim or crown
- Item tossed into a ring
- Item to talk through
- Item sometimes worn backwards
- Item in the ring
- Item for a ring
- It's sometimes passed for money
- It's sometimes passed
- It's hard on a construction worker
- It should go on a head
- It might be tipped
- It might be old
- It may rest on a rack
- It may go over your head
- It may collect tips ... or be tipped
- It may be tipped or blocked
- It may be tipped as a sign of respect
- It may be tipped (h)
- It may be in the ring
- It may be felt on your head
- It may be doffed
- It has a crown
- It goes right over your head
- It could be tipped off?
- Indiana Jones prop
- Hockey "trick"
- Helmet, essentially
- Head liner?
- Fez, for one
- Fez, for instance
- Fez e.g.
- Fedora, for one
- Fedora or fez
- Fedora or derby
- Fedora or beret
- Fan's purchase
- Easter Sunday accessory
- Easter parade attraction
- Dr. Seuss's "The Cat in the ___"
- Doffed thing
- Doffed item
- Do undoer, sometimes
- Do flattener
- Do damager, maybe
- Do cover
- Dicer or tile
- Dicer or skimmer
- Derby, for instance
- Derby or deerstalker
- Derby or bowler
- Derby of stovepipe
- Cracker breakthrough album "Kerosene ___"
- Cover for a bad hair day
- Collection holder
- Cloche, e.g.
- Cloche or castor
- Chef's accoutrement
- Caubeen, e.g.
- Castor or tile
- Castor or pillbox
- Castor or dicer
- Cardinal's symbol of office
- Busby or derby
- Broadbrim, for one
- Broadbrim, e.g.
- Breton or wide-awake
- Bowler, for example
- Bowler or sombrero
- Bowler or sailor
- Bowler or dicer
- Bonnet, for example
- Boater or derby
- Bit of dance attire for Fred Astaire
- Billycock, e.g.
- Bicorne, e.g.
- Beret or beanie
- Bella Abzug feature
- Beaver, e.g.
- Beaver or boater
- Bean covering?
- Bean cover?
- Balmoral or capuchon
- Baldness remedy?
- Bad-hair-day helper
- Article on a rack
- Apparel for a Dr. Seuss cat
- Alberta's Medicine ____
- Afro flattener
- Accessory for a Dr. Seuss cat
- Abzug trademark
- Abzug adornment
- 59Fifty product
- "You can leave your __ on"
- "Waiting for Godot" prop
- "Monopoly" token choice
- "Keep it under your ___!" ("Mum's the word!")
- ___ trick (three goals)
- ___ in hand (humbly)
- ___ in hand
- __ in hand (humbly)