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I workout in my Fivefingers shoes. I just can't jump rope anymore with regular shoes. Since I have them on, I'll lift with them. I run sparingly with them -- usually on 4 mile or less runs.
When swimming I have bare feet... everything else (stepper, elliptical, and workout videos) bare feet or tight fitting slippers (I work out in my house ) I guess I wear boots when I hike, but that's more for fun and sunshine than exercise.
My working out is always outdoors, so I've usually got on a pair of trail shoes. I had a paid of Nike ACG trail shoes for years but they needed replacing after I got water whomped on a rainy night by some guy in a red sporty vehicle. I upgraded to a pair of Hoka One One trail shoes and they are like foot pillows that keep you going all day long. Worth every penny.
I used to run a lot of races and always had my best times with Asics and Adidas running shoes. I always looked for a shoe that is as light as possible, but it still had a lot of heel support to absorb the continuous impact of a long run. If you can push the heel in with your hand on the bottom of the shoe (gel and air shoes, springy shoes, etc), it won't support your body weight very well. Asics and Adidas also happened to be on the cheaper side a lot of the time.
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