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Re:Clothing Britain’s Spies During World War II by toomanybeersies on Wednesday August 15, 2018 @09:50PM (#17771269)
I read somewhere a while ago that pilot's boots were specifically designed so that they would look similar to civilian shoes for the exact reason that they'd be able to blend in better.
Re:Clothing Britain’s Spies During World War II by NeedMoreTea on Wednesday August 15, 2018 @10:56PM (#17771557)
The RAF had escape pattern flying boots[0] from from mid-war. Looked like a normal shoe with sheepskin lined legging attached. You cut the top off with the included penknife to leave a normal looking shoe[1]. The leftover bits were designed to reassemble as a waistcoat if you needed to sleep rough.

Wouldn't be surprised if USAF had similar or maybe he was issued an RAF pair for having difficult feet. :)

[0] https://www.historicflyingclothing.com/en-GB/ww2-raf/raf-194...

[1] http://www.oldnautibits.com/assets/images/aeronautical/image...