In regards to winter clothing, Germans faced a stark choice - ammunition, fuel, food, clothing IIRC, in that order. Once more, basic rules of logistics nailed them and something had to give. It simply could not all be delivered in time. The operation was supposed to wrap up months before winter and logistic network was supposed to handle smaller amounts of supplies in terms of ammo and freed up bulk to be used for other items to support what by that time was hoped would be occupation forces.
It did not play out that way.
I just rushed to write an answer. Sorry once more.
It has been 20 years since I did a lot of reading on the Eastern Front, so I can't give sources.
The Germans had 1-2 winter uniforms per solider on the Eastern front, closer to 1 than 2. If identified as a critical resource, it could have handled. There were reports indicating the problem, but they were ignored. So they uniforms were sent as low priority items. Much arrived a late. Often soldiers in rear units took 2-3 winter uniforms. And as one got farther from the railheads, one became less likely to get the uniforms.
To be fair, many of the rear commanders did not know of the critical shortage in the relevant time window. If they had, much of the problem is fixed. And if I did not know it was a critical item, I might well have my men take two uniforms. An extra change of clothes is pretty standard/useful. A front line infantry unit may not be able to carry two uniforms with them, but at a Luftwaffe base or army support unit, it would be very handy to have a full change of clothes and coats.
As to the ammo/fuel shortages. First, the Germans did not have the workers work weekends/holidays for the first month or two. They worked the standard civilian schedule. There are a lot of other little things that could have been done, and were recommended to be done, but they have faded with time from my memory. These type actions show how overconfident the Nazi were, even before they attacked.
On ammo, the corp and army level reserves continued to fall on a weekly basis, even before the army was deep into Russia. Again the logistical recommendations were ignored.
While none of these problems could have been prevented 100%, they could have been made a lot less worse. But then we are down to the WW1 dilemma. If Germany knew how long the war would be, it would not attack.