Depends on how effective he wants to be.
I often sling a tablet case with my iPad Pro, ereader, battery pack, and charge cables. I use 100 feet of paracord strung up on daisy-chained slipknots with carabiners at both ends as my sling. Just a convenient way to carry my daily electronics and make sure I've got some paracord handy.
When I lived/worked in NYC, I used to carry a satchel. Satchels are easier to deal with mass transit/pickpockets/crowds/umbrella/chow/etc.
People who carry satchel looks like they are either bookie, loan shark, small business owner who carries cash. To me, it is a better version of money/deposit pouch with bank logo on it.
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Where else are gonna carry your 1st aid kit, survival knife, extra magazines, ect without looking tacticool?
In addition to my wallet I sometimes carry a holster with a G19 and a holder for extra mags. Does that count?
"If everyone is thinking alike, then somebody isn't thinking."
George S. Patton
"A people that values its privileges above its principles soon loses both."
Dwight D. Eisenhower
"Conformity is the jailer of freedom and the enemy of growth."
John F. Kennedy
?A motorcycle is a bicycle with a pandemonium attachment, and is designed for the special use of mechanical geniuses, daredevils and lunatics.?
George Fitch. c 1916.