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Drb

Band appears to be wool in lieu of velvet:

Wurttemberg

Uncommon to see portraits of female Reichsbahn employees:

Bavarian cap, not sure what for, but my guess is Tram:

Zweispitz SACHSEN Königlich Sächsische Staatseisenbahn

Sachsen Eisenbahn.
This hat was also in the above box.

Sachsen Platform Supervisor w/ original case:

Sachsen Saxony platform supervisor

Eisenbahner:

Eisenbahn officials captured by American troops.
(hat-tip: militariaone)

Eisenbahner:

Sachsen platform supervisor:

RB official:

Reichsbahn.

Credit: bluemax

He appears to be a KR Locomotive Engineer:

Reichsbahn portrait:

KR Platform Supervisor visors are uncommon to find.
Maker is August Pöker
Hoflieferant
Schüttingstraße 12
Oldenburg
1905 Goldene Medaille

From the Gunther Henneking collection:

This is for the Prussian Reichsbahn (railways). Doeskin wool body with a black velvet band. Hat is from an exclusive supplier to the Imperial court, the prestigious firm of Mohr & Speyer: