| Image | Costume | Seen in
|
 | Hatless | Where My Hat is At?, The King of Town DVD, Email super powers, Where My Hat Is At? (toon)
|
 | Starless | Marshmallow's Last Stand, Email different town
|
 | An explorer | In Search of the Yello Dello
|
 | An explorer | In Search of the Yello Dello Theatrical Trailer
|
 | A Minstrel | Tis True, Pom Pom, Tis True
|
 | Academic | A Jorb Well Done, The King of Town DVD
|
 | Charlie Brown-esque brown hat | The Best Decemberween Ever, Homestar Presents: Presents, Winter Store (Easter egg)
|
 | A clown | First Time Here?
|
 | A sailor | First Time Here?
|
 | A witch | First Time Here?, Homestar vs. Little Girl 2
|
 | Homestar Runner's Sleepwear | Email caper, Homestar Presents: Presents, HomestarRunner.com: PAY PLUS!, Store Thank You Messages, Weclome Back, Email secret identity, Email slumber party, Email nightlife, Email email thunder, Hremail 49
|
 | The Jolly Dumple | Email mascot, Email 4 Branches, On Break
|
 | Fake arms | Email fingers
|
 | Strong Badian Forefather | Email colonization, Hremail 62
|
 | "Col-on-el" Homestar | Email army, Labor Dabor, Email more armies, Strong Badia the Free
|
 | With cool shades | Email the bet, Bug in Mouth Disease
|
 | A scientist | Email stupid stuff
|
 | Duckie Shirt | Email flashback, Main Page 20, Main Page 24, The Homestar Runner Gets Something Stuck In His Craw
|
 | The Office Dullard (various polo shirts) | Email other days, Biz Cas Fri 1, Biz Cas Fri 2, Biz Cas Fri 3, Email cliffhangers, Email from work
|
 | "The #1" shirt | Email montage
|
 | With Daisy Dukes | Email long pants, Email email thunder
|
 | Dressed up for Halloween | Halloween Intro
|
 | With a sweater over his head | Email space program
|
 | With corn flakes on his face | Email death metal
|
 | With a red chef's hat with googly eyes and an apron. | Email narrator, Homestar Ruiner
|
 | Bunmaker | Email disconnected
|
 | Burglar | Email candy product
|
 | Desire Man | Sbemail 150?!?
|
 | In a tuxedo | Email senior prom
|
 | The Prom King | Email senior prom
|
 | With a headset | Email isp, Baddest of the Bands
|
 | A waiter | Summer Short Shorts, Date Nite
|
 | A Construction worker | No Hands On Deck!
|
 | Covered with sticky notes | Email trading cards
|
 | Wearing his L.U.R.N. uniform | Email coloring, Career Day
|
 | A newsboy | Happy Hallow-day
|
 | A bad boyfriend | Email 4 branches
|
 | White shirt | Email strong badathlon
|
 | With a horned helmet | Flashforward, Email the movies, Ever and More, Email dictionary (Easter egg)
|
 | Wearing a black suit, tie and hat | Email your funeral
|
 | In a hat and trench coat | DNA Evidence, @StrongBadActual
|
 | First mate in the USS Flirtini | Date Nite
|
 | Wrapped up by The Paper. | Email the paper
|
 | Wearing a snorkeling mask and covered with blue dye. | Email mini-golf, Where My Hat Is At? (toon) (without blue dye)
|
 | As John from Embarrassing Educational Films | Email hygiene
|
 | Mountie | Email original
|
 | Poncho and sombrero | Email original
|
 | Cold weather police officer | Email original
|
 | Dashiki | Email original
|
 | College student | Email bike thief
|
 | Trash can | Email bike thief
|
 | The Pizz employee | Email pizza joint
|
 | Wearing several lanyards | Email business trip
|
 | On a leash | Email pet show
|
 | With shards of glass in his face | Email licensed
|
 | Blubb-O's server | Blubb-O's Commercial
|
 | Brown wig | SBCG4AP Gameplay Trailer
|
 | Black turtleneck sweater with a striped star on it. | Email love poems
|
 | Doctor Marvin Rubdown, wearing a black turtleneck sweater with a striped star on it. | Email love poems
|
 | Fake arms and a box | Email magic trick
|
 | Bandage on head | Play Date
|
 | Bandage and icepack on head | Play Date
|
 | Body cast and wheelchair | Play Date
|
 | Helmet | A Death Defying Decemberween
|
 | A sweater, white shirt, blue tie and pipe | A Death Defying Decemberween
|
 | Both his helmet and sweater | A Death Defying Decemberween
|
 | "A French long-jump champion with eight wooden legs" | Donut Unto Others
|
 | Wearing a blue Garrison Cap | Donut Unto Others
|
 | Wearing a monocle | Where My Hat Is At? (toon)
|
 | Wearing a newsboy hat | Where My Hat Is At? (toon)
|
 | Wearing a sweater made out of mistletoe | A Decemberween Mackerel
|
 | Wearing a fig leaf | April Fool 2014
|
 | Wearing a fake beard, suit, hat, and a Windows 98 microphone. | April Fool 2014
|
 | Wearing a Dixieland outfit | Fish Eye Lens
|
 | Wearing an "I'M WITH PROV" shirt | Dad's Garage & Friends - 11 Jul 2014, Dad's Garage & Friends - 13 Jun 2015
|
 | With a polo shirt, headset, and cinnamon on his face, saying "tertiary" with the Cardgage curse | Email too cool
|
 | As an Aquabat | The Aquabats Super Show Kickstarter
|
 | Wearing an apron, goggles, and a clothespin on his chin | Email parenting
|
 | Wearing a jacket and holding a hot jones | Email parenting
|
 | Wearing sunglasses and a jacket with Strong Bad | Email parenting
|
