One wears what ones bank manager allows for .
I used to wear as much ex russian & nato military surplus as i could get and dye it black , most of the colour settled down after a couple of washes and by wash 20 most of it was only good for the dogs bed .
The ex german para boots were good but not so hot to get off when you needed to go inside the house quickly, so I took to having a pair of strong poly bags by the door and some undoable cable ties so I could use the bags as galoshes
I did always go for a good pair of wellies with a decent cleated sole and for a long time used Century industrial wellies with a steel mid sole and steel toe cap as they were recognised safety gear and thus were VAT free ..not seen any for at least ten years , but then ..I've not been looking .
Hats were alway a soft wool balaclava usually rolled up unless it was very cold but mainly used because I could fit the safety hat on top if needed or a water resisting 2 inch rimmed floppy hat with chin strap fitted for the wet weather to try and stop rain cascading down my neck .
Glove were usauly hard chromed yellow riggers gloves with a pair of the thermal metalic liners in cold weather or a wrist lenght pair of industrial rubber protective gloves with a cotton liner in them as the rubber used to make my skin go funny.
High summer was stripped to the waist most of the time with a pair of cut down rolled up legged pair of brit army lightweight trousers for shorts with pocket . On the cooler days that were fine it was usually surplus T shits and a ski roll neck jumper with the surplus trousers that had lots of pockets and a bit of knee protection .