Items A New Driver Should Have With Them OTR?

Steel or Composite toe work boots/shoes.
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Skechers sells those as do several other places such as Boot Barn.
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I prefer slip-on work boots, but many drivers prefer lace-ups.
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Skechers has the largest variety to choose from.
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Clothes for all weather conditions

 

Composite & steel toe work boots:

 

Gloves, flashlight, hammer. Most everything else, pick up along the way or on home time after you figure out you need it. The problem with this question is you'll get everyone chiming in on what they personally have, that may or may not be relevant to what you're doing. You'll end up with a list of stuff so long you'd need one of those super sleepers to store it all. My advice is start minimal and expand from there rather than spend money on a bunch of stuff you end up never using.

 

CDL
Med Card
Fuel Card
Shaving kit

That's all that's essential.

 

Condoms.......lots and lots of condoms

 

And soap for after the act

 

Disco lights in the sleeper.

 

Cash or credit card as an emergency exit strategy