Cool thread idea!
Started in 2006, so I'll list the notable ones:
2006: some DC manteca looking shoes. Spark I think? Some etnies that looked like a puffy dunk with the "m" looking "E" where the swoosh would be (just to paint the picture)
2007: Es Cassette Mid, Es Anti Social (all time favorite shoe) AV Era (amazing shoes)
2008: Van's AV Era again (AWS collab) can't remember much else from 2008, Circa 205 vulcs, Es Koston 7
2009: Lakai MJ3 (loved them even though I broke my foot in them) Es Square Ones, Fallen Chiefs, Circa Ramondetta Real mid tops (in green!), Etnies Arto 2 (beautiful shoes)
2010: Globe Encore (amazing shoes), Converse: Star Player S [midtop] (a puffy chuck, it's the best version of a skateable chuck, in my view) Emerica Hsu mid (one of the best I've skated), some iPaths made out of canvas/hemp that skated great but the sole detached from the shoe.
2011: Etnies Jameson 2 (when they were cupsole and not vulc), Es Accel TT, Emerica Hsu Mid (again!)
2012: Fallen Slash (1st model) I know there's more but I can't remember or find photos
2013: DVS Munition CT, Nike 6.0 Mavrk, Etnies RVM, Classic Vans Half Cabs (one of the best)
2014: Circa Talon, Emerica Jinx, Herman G6 (easily the best shoe ever made, no questions asked) Etnies Marana (started my love for my favorite current shoe available)
2015: Osiris Sleak, some leather Converse Cons that were amazing! Nothing like their chuck, looked more like other skate shoes, actually.
2016: Etnies lo cut (remaster version) and Pro Leather Cons (still miss these shoes), Adidas Seely (non skate), Lakai Riley Hawk 1, Fallen Chief XI
2017: Es Accel Slims, Cons KA-One, Etnies Marana, State Mercer/Madison, Nike SB Blazer Mids, Nike SB Check, Lakai Staple (reissue)
2018: Nike SB Blazer Mids, Etnies Joslin/Marana, Van's Kwalks, Gilbert Crockett 2, Evan Smith Hi Zero, Etnies Jameson Vulc MT (at least a couple pairs)
Too many shoes I've dabbled with from 2018-2020 so what I'm listing isnt exhaustive. I tried more shoes than my wallet/time should have allowed me to, so a lot of my experimental ones aren't listed.
2019: Reynolds G6, Maranas/Joslin, Van's KWalks, DC Maswell
2020: Maranas/Joslins, DC Maswell, Nike SB Dunks, Lakai Proto/Atlantic, Etnies Veer, Es Accel Slim Plus, Half Cab Pro
I plan on skating Kalis S, NB# 440, AVE Pro, Romero Americana, and Joslin 2 in the near future.
I generally skated cupsoles more than vulcs but there were some exceptions when vulcs were actually good and supportive (most are shit nowadays) so I skate padded cups more regularly now.
I applaud you if you read all this! Hahah