Hobo tips: survival is the ultimate sport Spartan 10/13/2017 (Fri) 00:50:58 No. 129053 del
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My protips: wear polyester undershirt, undies, longjohns and polyester dress pnts, leather jacket or polyester windbreaker or blazer, get the Summerweight Ozark trail 40 degree bag from Walmart or other similar supermicro bag, and a messenger bag to put that and your laptop in. Get some dress shoes with a walking sole. Get polyacrylic hiking socks. -homeless four years and counting. Thanks America
Oh yeah and wear a white silk or polyester dress shirt. White cotton gets grimy instantly, silk looks great for months without washing

Also you can maybe try just buying a sleeping bag liner, for warmer months that will fit in your pocket. Switch from tablet to cheap tracphone android.

Another good investment would be a cheap roadbike, then plop 200$ to put tannus airless tires on it. Zoogachooga