I usually wear dark wash jeans (usually Lucky brand), unless I'm wearing a light, royal, or navy blue top, in which case I wear medium wash. In warm weather, I wear shorts, usually American Eagle longboards with a 12" inseam, I don't do that mid-thigh shit. I have pairs in light khaki, navy, stone blue (really a gray), a pale light blue, and one plaid pair that's light blue/navy on white. It all depends on what top I'm wearing.
For tops, I usually wear t-shirts, henleys, button down shirts (striped, plaid, and a handful of solids), or a polo, usually Lacoste. Wearing the appropriate jeans or shorts is ESSENTIAL.
Also essential is matching the right sneaker or shoe with the outfit. I usually wear slip-on Sperry Top Sider sneakers or boat shoes, or a classic casual sneaker such as Nike Cortez or suede Pumas. I try to have white, navy, royal blue, gray, and black. That will usually match up with anything, although certain styles only work with either jeans OR shorts, they're not always interchangeable. The Sperry sneakers usually work with both though.
My overall look is semi-preppy, but not THAT preppy. I think it's more just "normal" casual wear, with a tinge of preppy, if I'm wearing the Sperries. But I don't generally wear khaki pants casually, or roll the cuffs up, or tie sweaters around my neck or anything, haha. I don't try to look like I belong to a yacht club😂 I just try to dress appropriate for my age, without looking like an out-of-touch old man and maintaining a semi-young style. I'm just too old to be wearing Jordans and whatnot, haha. The goal is to look well-put-together.👍