This is Garland in a relaxed, unhurried mood — ballads done right, no showing off.
By 1962, Red Garland had already made some of the most enjoyable piano trio records of the late 1950s, particularly his work with Miles Davis and his own sessions for Prestige. When There Are Grey Skies (1963) is a later entry in that run, and it shows a pianist who had settled comfortably into his style — the block chords, the light touch on the keys, the easy swing — without pushing himself into new territory. That's not a knock. If you like what Garland does, this album delivers it consistently.
The repertoire leans heavily on standards and older popular songs, which suits the mood. The title track sets the tone early — slow, gentle, a little nostalgic. Garland was always better at this kind of intimate balladry than he gets credit for, and here he lets the melodies breathe without overloading them with ornamentation. The rhythm section keeps things moving without crowding him, and the interplay is relaxed in the way that only comes from musicians who've played this kind of material many times before.
Where this album sits in Garland's catalog is pretty clear: it's not essential in the way his mid-to-late 1950s trio dates are, but it's a genuinely pleasant listen and holds up well in the right context — late evening, low volume, no demands on your attention. If you're already a fan, it fills out the picture nicely. If you're new to Garland, start with his earlier Prestige work and come back to this one when you want something quieter. It's a solid record from a pianist who knew exactly what he was doing and had no particular interest in pretending otherwise.