I had some canvas Allstars back in the day but never had a pair of leather ones. My wardrobe was greatly simplified when I moved to California. You could go anywhere in a pair of shorts and a polo. No more ties or jackets for me. Now its more jeans and tshirt but same idea.
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Milder weather = easier wardrobe! We always laugh at Queenslanders with their endless tshirts and shorts, totally unprepared to visit our state in the south!