This answer is a community wiki, feel free to add in any hats that may be missing from the list.
For a list of common hat designs, see Which Winter Bash hats were reused in past years?.
Earn a silver badge
- 2013: Hi Ho Silver
- 2014: Werewolf Hunter
- 2015: Cerro de Potosi
- 2016: 925
- 2017: IDENTIFICATION DIVISION
- 2018: IDENTIFICATION DIVISION
- 2019: Amazing Grace
Earn a gold badge
- 2013: Mr. Peanut Monopoly McDuck
- 2014: Treasure Hunter
- 2015: El Dorado
- 2016: 24
- 2017: Foot of the Rainbow
- 2019: Foot of the Rainbow
Reopen or undelete
- 2013: Reanimated
- 2015: Thalia
- 2016: No Longer Grinchy
Help find 20 unique hats
- 2015: Every! Body! Gets! A Hat!
- 2016: Just Here for the Hat
- 2017: And YOU Get A Hat!
Wear different hats on different days
- 2016: Trendsetter (5 hats on 5 UTC days)
- 2018: It Ain't Easy Being Cheesy (6 hats on 6 UTC days)
Accepted answer to Tumbleweed
- 2015: Weed Eater
- 2016: Lifesaver
- 2020: Backlog (answer an old question with no answers)
Collect a number of hats
- 2013: The Milliner (collect 20 hats)
- 2014: Aztec (collect 20 hats)
- 2015: Specialist Hatsman (collect 11 hats)
- 2016: 011 (collect 11 hats)
- 2017: The Milliner (collect 11 hats)
- 2018: Propel Thyself (collect 3 secret hats)
- 2019: The Milliner (collect 11 hats)
- 2020: Milliner (collect 11 hats)
2021: Propel Thyself (collect 3 secret hats)
Answer own question
- 2012: Git R Done
- 2013: Sock Puppet
- 2014: Selfie
- 2015: Do it Yourself (both q & a +3)
- 2016: Egoist (both q & a +3)
- 2017: Sherlock (both q & a +3)
- 2019: Living in the Future (answer +5)
Answer a question with an already accepted answer, get upvotes
- 2017: Extra Toppings (+3)
- 2018: Pizza Hat (+3)
- 2019: Shiver Me Timbers (+2)
Nice question asked via app
- 2015: Field Work
- 2016: Loungin' Around
Search on 3 consecutive days
- 2015: Researcher
- 2016: Search You Must
- 2017: Fascinator
Rep cap
- 2012: Just Jesting! (1 time)
- 2012: Monarch by Right (5 times)
- 2013: R-E-S-P-E-C-T (1 time)
- 2015: Hat Trick (3 times)
- 2016: Third Time's A Charm (3 times)
- 2017: Rep Cap (1 time)
Close or delete
- 2015: Melpomene
- 2016: Abominable
Answer in 30 min, +3 and accepted
- 2015: Speedy Delivery
- 2016: Snaphat
- 2019: Snaphat
- 2020: Snaphat
Manually awarded by SE staff to users who guessed how to get a secret hat
- 2013: Eureka!
- 2014: Eureka!
- 2015: Archimedes
Post/vote on meta
- 2015: The Airing of Grievances
- 2016: I Am Your Father
- 2020: Social Distancing (Meta) (it's enough to visit a question page on Meta)
Vote via app
- 2015: Wireless (10 times)
- 2016: Cutting the Cord (7 times)
- 2017: Too Cool (7 times)
Answer a -3 question; later +3
- 2014: Red Baron
- 2015: Flying Tiger (answer needs to be +5)
- 2016: Maverick
- 2017: Waffles
- 2018: Red Baron (answer needs to be +5)
Tried for a bounty, but didn't win it
- 2013: IG-88
- 2016: This Is Fine
- 2019: This Is Fine
- 2020: This Is Fine
Pinging an SE employee
- 2014: Hairboat (ping Abby Hairboat)
- 2015: Hairboat's Revenge (ping Jon Ericson)
Posting a question at a specific time somewhere in the world and upvoted
- 2015: It’s Always 5 O’Clock Somewhere (at 5:01 on Friday)
- 2016: The Hatter (at 6:00)
- 2017: Hero Of Time (at 7:00)
Specific number of answers with a specific score
- 2014: Full House (three answers with +3)
- 2015: Do You Even Lift? (five answers with +5)
- 2016: Fiery (five answers with +3)
- 2017: Taco Tuesday Any Day (five answers with +3)
- 2020: Rep Hunter (ten answers in one day with +1)
Start a bounty
- 2013: Make It Rain
- 2016: Philantropist (on last day of WB)
Do a number of reviews
- 2012: Le Magritte (5 reviews)
- 2013: Do the Swim! (5 reviews)
- 2014: Joga Bonito (10 reviews)
- 2016: They Live (5 reviews, using either "Improve Edit" or "Reject and Edit")
- 2018: Peacekeeper (20 reviews, without failing an audit)
- 2020: Bouncer (close vote reviews), Doorman (reopen vote reviews), Chimney Sweep (suggested edit reviews) (3 reviews of the given type that get handled the way you recommended)
Edit question closed by others, gets reopened
- 2015: I’m Batman
- 2016: Hero of Questions
Vote to close, edit, vote to reopen
- 2014: Breaking Bad
- 2016: 180°
- 2017: I’ll Handle It
- 2018: I’ll Handle It
- 2019: 180°
Accepted answer with no votes for 12h
- 2014: Naruto
- 2016: Mild Mannered
- 2017: Explorer
- 2018: Explorer
First post, +3
- 2015: Explorer (post 3 days old)
- 2017: Mother of Dragons (post 3 days old)
- 2018: Member of The Hand (account 1 week old)
- 2019: Mother of Dragons (post 3 days old)
Post 10 comments that each earns an upvote
- 2016: Blue in the Face
- 2017: Just Jesting
- 2019: Just Jesting
For 6 separate questions or answers, post gets edited by owner after you comment on it
Delete a number of comments after owner edits post
- 2015: Cleanup Crew (10 comments)
- 2016: 8,243,721 (6 comments)
- 2017: It’s-a me! (6 comments)
- 2018: It’s-a me! (6 comments)
Answer +7 with no comments on Q or A
- 2015: 007
- 2017: Silencium
- 2018: James Bond
- 2019: 007
Earn 150 rep on three non-SO sites in 15 days
- 2016: Running Ragged
- 2017: Brunhilde
- 2018: Brunhilde
Star chat item on a specific day
- 2012: New Year's Eve Hat (on New Year's Eve)
- 2013: Winter Is Coming (on Dec 20)
- 2013: “First!” (on New Year's Day)
- 2014: Tam o' Shanter (on Dec 31)
Starred chat, ±12h from Jan 1, 0:00 UTC
- 2015: Auld Lang Syne
- 2016: First Responder
- 2017: Glasses With A Number On Top
- 2018: Glasses With A Number On Top
- 2019: Glasses With A Number On Top
- 2020: Glasses With A Number On Top
Post or vote on winter solstice (Dec 21 or Dec 22)
- Dec 21
- 2014: Solstice (post or comment)
- 2016: Where In the World?
- 2017: Some Kind Of Sun Thingy
- 2019: Where In the World?
- 2020: Where In the World?
- Dec 22
Post or vote on Dec 25, Christmas Day
- 2012: Tis the Season
- 2013: Ho Ho Ho
- 2015: O Tannenbaum
- 2016: Bûche de Noël
- 2017: Red Hat With White Fur Trim
- 2019: Bûche de Noël
- 2020: Bûche de Noël
Post or vote on (on other days)
- 2012: L'chaim (on Dec 16)
- 2013: L'chaim (on Dec 5)
- 2014: Saint Lucia (vote on Dec 15)
- 2015: A New Hope (on Dec 18)
- 2015: Sufganiyot (on Dec 14)
- 2016: Mmmm Bacon (on Dec 30)
- 2016: Epiphany (on Jan 6)
- 2016: I Have A Little Dreidel (on any of the days of Chanukah)
- 2017: Row Of Many Candles (on Dec 20, last day of Chanukah)
- 2020: Cruse of Oil (on Dec 18)
