Frankly, I rarely do.
At work, I now must dress up - at least nice slacks, long sleeve shirt and tie but sometimes a suit or at least a sport coat.
When not at work, it's shorts and a T-shirt (or maybe polo shirt). Even when it's pretty cold (even when it's raining). A result, I suspect, of growing up and living in coastal southern California. I have jackets and sweatshirts - I just avoid them whenever possible. And even if I'm wearing a jacket or sweatshirt, I'm probably still wearing shorts.
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