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To me "Old School" gaming is defined by a few points...
1) Mechanically simpler.
Basically, a less cluttered game system like the Basic/Expert/Advanced D&D of yore. Pen, paper, dice, and an imagination were all that was required.
Nothing much to bog you down like having to stop and map every room for miniature placement, tactical feats that depended on the physical placement and/or facing on these squares, etc.
2) Improvising on the fly.
If you ran into something not covered in the rules, you "winged it" for the most part based on existing rules from the books for similar situations.
This is a fairly large grey area to just about everyone.
For me it starts with a more "Savage" over "Magical" backdrop. This has nothing to do with martial over magical though i hate the term "Low Magic" setting, it's more a world where not every tavern keeper is a 6th level retired Warrior, or every sage is a former 9th level Wizard. There's a reason we have heroes, and they should be rare. That's how legends are made. For example, back in the FR days, my players would joke that if they failed Elminster or another godlike NPC wouldn't let things end badly for the Dales or wherever else we were at the time. Hell, why was a 6th level Warrior barkeep even bothering to hire us to begin with when he could easily solo the problem or call an old bandmate to help him?
We knew as players what the goals were and what we were there for, but there was a slight disconnect nonetheless.
Next is the feel of the backdrop. Classic tropes of old (semi-sacred cows). Evil power hungry Wizards, Evil cults with grand plans to restore an old god, Remote exploration/survival, be it in the icy northern mountains, underground or even a more exotic extraplanar locale.
Even in the usual uber "Dungeon Crawls", my group managed to turn the original Temple of Elemental Evil into an unbelievably role play heavy experience with great character personalities, moral dilemmas, etc.
Additionally... there's Art style. This is purely a personal preference but it helps for me.
It's a little hard to explain but artists like Erol Otus, Jeff Dee, and DeTerlizzi (not sure of the spelling) really brought things to life in their projects with original kind of art styles. Goodman Games bottled that same kind of lightning as well with artists like Chuck Whelon, Jason Edwards, Michael Erickson, and William McAusland for the feel of their specific line.
Artist like Wayne Reynolds (while great for the newer stuff) drawing warriors with Final Fantasy-esque swords just don't do it for me like the "old schoolers" do. I absolutely love the art in RotR, Carrion, Shackles, and Kingmaker for example, but they can never be considered "old school" in flavor for me, though they do bring their own particular "pathfindery" art style. Hope my choice of wording makes sense to some of you reading this :).
Lastly... The much talked about lethality of the old adventures like Tomb of Horrors, Castle Ravenloft, etc. Early Pathfinder AP volumes are no less lethal (read those AP obituaries, lol). Overall, I don't mind running them as long as players are warned in the beginning of the difficulty and agree play in it.
DMs as usual are the ones ultimately responsible for making or breaking of any game here (it's not just player lapses in judgement or bad decisions like the classic greedy Rogue "scouting" too far ahead on his own to palm valuables before the rest of the party gets there to liberate and divvy up loot).
People tend to forget we (us DMs) have SCREENS to roll behind. I use to keep a secret log of where and when characters actually would have died if not for my mercifully secret "fudged" die rolls behind the screen (like barely missing the PC or falsely lessening trap damage, etc) to keep them alive. But to keep on target, Lethality of said adventures is "kinda" (but far from limited to) old school.
Just my 2 coppers.