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This was just supposed to be a 5 min doodle, but whoops. Just wanted to draw Sonic in a letterman jacket and Vans inspired shoes. 🤓 #Sonic #SonicTheHedgehog #Fanart
Commission for MunchMonster of their fursona with a cool letterman jacket and 50s diner vibes!
More recent art and designs. Some letterman jackets and some t-shirt designs.
Rei The Bunny 90s style! If I wasn't a boy back then, this totally would have been my style. Sporting a Letterman jacket and walkman, this bunny is totally styling. Thankyuu to @shadousu for such a wonderful piece of art!
#reddie college au!!
"star track athlete Edward Kaspbrak letting his lanky mathlete boyfriend Richard Tozier wear his letterman jacket even though the arms of it are a bit too short for him. that’s it."
-andevenifweforget (tumblr)
Proud of this one :3
I really like Letterman jackets 🤔 maybe I'll draw more characters in them
#furry #furryart #digitalart
getting to draw my own characters for a comm is always nice, and @arkson10 wanted autumn Oliver who definitely wears a letterman jacket and dumb shirts
Hunktober Day 11: Letterman Snowleopard, What kind of sport is he into? #Inktoberday11
6.
I love her casual style the most. She looks super cute in those letterman? jackets especially when combined with a skirt or dress. She also of course looks great in more traditional stuff (I'm really hoping her next ssr is kinda like the 3rd pic) Shes cute in everything aaa
I couldn't fall asleep last night and spent like an hour watching old Pee-Wee appearances on Letterman
It's my sister's birthday today, and she just moved into college (Ringling, no less), so I decided to draw her in a classic college-letterman jacket as a gift.
I guess she would qualify for #cutiesaturday as well? I wouldn't disagree.
@cutiesaturday
Bernadetta in a letterman
#art #digitalart #FireEmblemThreeHouses #BlackEAgles
i thank god so many of these dollmakers include letterman jackets https://t.co/vgRNNhPJJP
Supergirl! Thanks @ mr.unfunkyle for giving me the letterman’s jacket idea. Those teased bangs were unavoidable
#illustration #digitalart #dccomics #Supergirl
I saw that new steven has a pink letterman jacket now and I had the uncontrollable urge to draw him in mine #StevenUniverseTheMovie ✨