From Homestar Runner Wiki
There are many references to characters wearing cool shades (or cool glasses). Often characters will be seen wearing sunglasses or other eye-wear.
 Homestar Runner's shades
Homestar Runner wears shades often. He has worn different styles of sunglasses, but they are all very similar. Oddly, Homestar does not have any visible ears or a nose, so it is a mystery as to how these shades are held up.
- Debut: Main Page 3 — He wears them here when he says "Downloads!"
- Email the bet — He wears them while looking cool.
- Everybody Knows It — Puppet Homestar wears a pair of real-life shades.
- Email dangeresque 3 — He wears shutter sunglasses when he stars as Dangeresque Too.
- Bug In Mouth Disease — He wears them during his cameo appearance on Caleb Rentpayer.
- Cool Things — Bubs slips a pair into a can of Yella Paint.
- Sketchbook — 18 Oct 2007 edition featured a storyboard of Homestar trying to order cool shades.
- Dangeresque 3: The Criminal Projective — Homestar dons his shades again as Dangeresque Too.
- Poker Night at the Inventory — Strong Bad bets Homestar's Dangeresque Too? shades.
- Team Fortress 2 — By winning Homestar's Dangeresque Too? shades in Poker Night at the Inventory, they can be worn by the Demoman.
 Strong Bad's shades
- Dangeresque wears sunglasses as part of his costume.
- Everybody To The Limit — Strong Bad wears wraparound shades.
- Happy Hallow-day — Strong Bad wears shades as part of his Halloween costume.
- Email keep cool — Strong Bad wears shades when he's the lifeguard at the pool.
- Email the movies — Dangeresque's glasses now have three lenses, probably for the "upcoming" third film.
- Email yes, wrestling — Strong Bad wears shades as part of his Wild Vacationers costume.
 Other characters' shades
- The Thnikkaman, Olda Boys, Fatty, Gunhaver, Crack Stuntman and Tenerence Love always have sunglasses as part of their outfits.
- Stinkomanual — The Liekand is described as having "firm resolve and sweet shades"
- 3 Times Halloween Funjob — Coach Z and Strong Mad wear shades as part of their Halloween costumes.
- Email suntan — The King Of Town wears shades when he steals Strong Bad's cocoa butter.
- Email mile — The Cheat wears shades when he's a millionaire.
- Halloween Fairstival — Bubs wears shades as part of his costume.
- Halloween Potion-ma-jig — Pom Pom is wearing shades as part of his Halloween costume.
- Teen Girl Squad Issue 8 — Cheerleader wears shades when trying to convince the others to form a band.
- Weclome Back — The Poopsmith and Pom Pom wear Dangeresque's sunglasses in an Easter egg.
- Happy Hallow-Day — Strong Sad wears shades as part of his Halloween costume. The Goblin shows up in sunglasses and swim trunks. Bubs offers "Halloween Night vision goggles", which are really just sunglasses.
- Email space program, cliffhangers & Career Day — The Cheat wears cool shades as part of being Harold "Strap" Coopmore.
- Email technology — Pom Pom wears shades when he's a director.
- Email theme song — The Cheat wears shades during the first theme song.
- Email strong badathlon — Powered By The Cheat segment features The Cheat in sunglasses and playing a guitar
- Email from work & bike thief — Pom Pom is wearing shades and carrying a bicycle when he appears.
- Jibblies 2 — The Poopsmith wears shades as part of his Halloween costume.
 Other glasses
- Senor Cardgage, Reynold, The Ugly One, Mr. Shmallow, Dee, Cardboard Homestar, Other Little Girl, Ted Averill and the sloshy bassist wear glasses regularly.
- Strong Mad is sometimes seen wearing reading glasses.
- Strong Sad often wears half moon glasses.
- Homestarloween Party — Glasses are part of Strong Sad's costume.
- The House That Gave Sucky Treats — Coach Z, Pom Pom, Bubs and Strong Sad wear glasses as part of their costumes.
- 3 Times Halloween Funjob — Marzipan and Strong Sad wear glasses as part of their costumes.
- Shopping For Danger — Fightgar wears glasses as part of his old lady disguise.
- Halloween Potion-ma-jig — The King Of Town and Strong Sad wear glasses as part of their costumes.
- Email stupid stuff — Homestar puts on glasses in an attempt to look smart.
- Email other days — Strong Sad wears swimming goggles.
- Email modeling — Strong Bad wears glasses as part of a business suit.
- Email highschool and imaginary — Teen Strong Mad wears glasses.
- Teen Girl Squad Issue 11 — Cheerleader wears half-moon glasses when she asks, "Does 'ugs' have one 'g' or two?"
- Email keep cool — Marzipan wears swimming goggles.
- Email theme song — The Cheat has glasses in the Powered By The Cheat segment.
- Teen Girl Squad Issue 12 — Patchbeard and Band Name Boys wear glasses.
- Main Page 24 — Pressing Store puts glasses on the viewer, allowing them to see the page better.
- Email mini-golf and Where My Hat Is At? (toon) — Homestar wears snorkel goggles.
- Email concert — The Poopsmith wears snorkel goggles in the mud baths.
- Email slumber party — Strong Bad's illustration of "Prof. Tor Coolguy" has him wearing glasses.
- Jibblies 2 — Homestar, Strong Sad, and The Cheat all wear glasses as part of their Halloween costumes.
- Everything Else, Volume 3 — A pair of glasses appears in the maze the second time The Cheat goes through it on the Holiday Toons menu.
- Best Caper Ever — A sketch of The Cheat wearing glasses while working with the time-space continuum appears.
- A Decemberween Mackerel — Marzipan wears half moon glasses when writing her letter.