What kind of clothes did he wear? Shopping for clothes is a major pita, so he must have always bought the same thing, readily available everywhere?
Also, aren't new clothes full of all sorts of chemical? Better to have washed clothes... (Personally I sometimes get skin reactions from wearing unwashed new clothes).
Author Lee Child has written a series of fictional novels which feature Jack Reacher, a former Major in the United States Army Military Police Corps.
Since leaving the Army, Reacher has been a drifter. He wanders throughout the U.S. because he was accustomed to being told where to go, when to go and what to do for every day of his life from military childhood to military adulthood. He also felt he never got to know his own country, having spent much of his youth living overseas on military bases and at West Point. He usually travels by hitchhiking or bus. As a drifter, the only possessions he carries are money, a foldable toothbrush and, after 9/11, an expired passport and an ATM debit card.
He wears his clothing for 2–3 days before discarding it, usually purchasing new clothing cheaply from chain outlets. He has no steady income and lives on savings in his bank account and part-time jobs. Since he has no fixed address, Reacher often eats in diners and other inexpensive restaurants.
Except that they're fictional and any time he runs into a bind something falls out of the plot hole to save him. It's not a very good way to reflect on how someone would deal with that situation in real life.
And, even without plot holes, a lot of the strategies that he uses work for him because he's a huge guy, with years of hard experiences in the military police. For example, he may have problems getting people to pick him up when he hitch-hikes, but he rarely needs to worry about his own safety with whoever gives him a ride.
I agree clothes shopping can be 'a major pita', but I suspect with the right level of wealth and a carefree attitude, it need not be. Just overbuy things that seem right; who cares if they don't fit well or no longer seem stylish after the first wearing? And at very high-end outlets, the staff will be better at making good recommendations at a glance, you may get to know the consistent sizing/cuts, and the aura from the brand/style can cover up minor issues. (Wear something expensive confidently and it seems that's how it's supposed to fit.)
Also, aren't new clothes full of all sorts of chemical? Better to have washed clothes... (Personally I sometimes get skin reactions from wearing unwashed new clothes).