I would also say 50's-60's.
Lining doesn't look like silk, more like sateen. Most likely rayon or polyamide.
The flecky fabric would also suggest 50's.
Buttonholes don't look so old.
Buttons could have been changed, but if they are original they are plastic, not even bakelite.
Use Valmour Saphir Renovateur, neats foot oil or Pecard's Antique Leather Dressing to treat them before use. This will reinvigorate the leather so it doesn't tear, split or crack. After you have applied enough thin layers on the leather and it does not absorb the product anymore you can wipe or...
I bought these shoes for my girlfriend. They are early 20's judging from the elongated toe shape (not almond, like usually in the mid-to-late 20's)
They need a little attention with the heel but otherwise in great condition. Hardly walked in.
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