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. Although, none of the main characters have any visible ears or noses (with the exception of Strong Mad), so it is a mystery as to how these glasses are held up.
 Homestar Runner's shades
Homestar Runner wears shades often. He has worn different styles of sunglasses, but they are all very similar.
- 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
Like Homestar, Strong Bad has been known to wear shades, especially as part of a costume.
- 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.
- I Killed Pom Pom — Strong Bad wears shades as part of his Halloween 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".
- Homestarloween Party — Coach Z wears shades as part of his costume.
- The House That Gave Sucky Treats — Marzipan wears shades as part of her costume.
- 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 and Coach Z wear shades as part of their Halloween costumes.
- I Killed Pom Pom — Bubs wears shades as part of his 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.
- Most in the Graveyard — Coach Z wears glasses as part of his costume.
- Best Caper Ever — A sketch of The Cheat wearing glasses while working with the time-space continuum appears.
- Doomy Tales of the Macabre — Homestar wears glasses as part of his costume.
- A Decemberween Mackerel — Marzipan wears half moon glasses when writing her letter.
- Which Ween Costumes? — Strong Sad wears glasses as part of his costume.
- Halloween Safety — Crack Stuntman's sunglasses appear on the pupil in the eye-shaped sign in an Easter egg.
- I Killed Pom Pom — Homestar wears glasses as part of his costume.