We’re discussing this on Soho Radio at the minute http://sohoradiolondon.com/
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With guitar-based albums, there’s a certain kind of jangly tone that seems very autumny for some reason. Early Sonic Youth (especially Sister) has it in spades.
Certainly a kind of lo-fi yet colourful or rich feel to an album’s production helps as well. A lot of shoegaze, I guess.
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Oddly enough I finally got around to getting a copy of What’s Going On by Marvin Gaye, and the first thing I thought of when I heard it was how autumnal it was. dunno why. think it’s the crisp sound of everything, and the fact he’s wearing a big coat on the front cover maybe.
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Find myself listening to Nick Drake, Banhart, Grouper, The Acorn, Microphones, general moody acoustic or ambienty folk in autumn and winter.
First day of summer Cut Copy, The Strokes, Nas, Jay Reatard, various other completely unrelated but i guess a hit more uplifting records.
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Anything by Do Make Say Think innit
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The Autumns
Hood’s ‘Cold House’ is my go-to autumn album. So I guess anything that sounds like that? 
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Folky acoustic guitars for me. Not sure why but they’re inexorably linked to autumn visuals in my head.
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Early REM albums. Murmur and Reckoning; that sort of sound for me.
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That’s very much winter for me
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As said upthread - warm jangly guitar, melancholy lyrics, Scottish accents. Idlewild and the Twilight Sad only sound their best when the leaves are brown.
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Red House Painters, Polvo, Lungfish. Anything like that
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Early Magnetic Fields does it for me in autumn, first few albums have that aching melancholy thing going on
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It is by Yo La Tengo
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The Walkman - you and me
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Me with nothing to say that disagrees with this statement and you in your autumn sweater having made the statement
Codeine
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Always Buffalo Tom for me. Mid period.
Great call on the twilight sad if it’s first album or the early eps
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