The original "OP" clothing line seemed to be typically for the leaner build guys, even if the waist sizes were "not lean". Larger thighs just did not work if you bent your knees, by observation. While the OP cord shorts looked great on the taller and leaner and what you might consider "surfer dude" guys, the leaner legs didn't work for me. They had some really neat t-shirts, though!
In those earlier '60s and '70s times, "walking shorts" were the norm for the well dressed guy that didn't wear denim cut-offs (putting a hem in those denim shorts would have been a sin!). They usually were mid-thigh in length, or an inch or two above the knee when standing. For some reason, men's knees seemed to be "knobbier" back then. The more athletic guys wore white socks and "gym" shoes, whereas others might wear dark dress socks and similar shoes. Madras??? Yep! Seems like I recall some pictures of guys in madras walk shorts, dress shoes and socks, dress shirt and a TIE.
Back then, there was no "loose" cut, just "normal" of sorts. Same with blue jeans. You bought what fit and that was it. If you were lean or normal, you didn't seek out the "husky" fit for more room unless you needed it. The looser cuts were initially for "more mature" (40-ish) guys that had moderate "middle age spread" and needed more "seat room" (circa 1975), or "hip and thigh" (as they put it in the ads).
In general, the "cut-offs" (whether store-bought from Sears--various fabrics other than denim--or home-made) were mid-thigh when standing or a little shorter. Keeping the "strings" trimmed made them look a little nicer (rather than the longer strings which made them look "uncared-for"), but were part of the situation. With that just-above-mid-thigh (when standing) length, that meant that a slightly muscular thigh looked really sexy (especially with a tan and some body hair) and it would ride up to the top 1/4 of the thigh when seated. HOT, especially for a guy on a motorcycle! To me, that was the best inseam length, although it might take some trial-error to get it right.
For me, 2.75"-3" inseam works best for outside wear. Just enough to keep things snuggled inside when I sit. This is for normal Levis, depending upon whether it's 505s or 550s.
In more recent times, I've just bought the 9" inseams and wear them as normal. To me, it looked flaky for a guy to wear shorts and have a horizontal "wear stripe" across the back of his calves where the shorts touch them as he walks. When I put on the older pair of 2.75" inseam denim shorts, they just feel fantastic compared to the longer inseam shorts. Next spring, I'll probably get some more denim shorts and get them shortened to about 4.5" inseam and see how that works.
As mentioned, the issue of pockets being visible can be an issue. Once they start doing that, you can't stop it. But if they "retract" when standing, that works ok for me.
Several years ago, a group of Swedish men came through work on a tour. They were wearing their native shorts, which basically were about 1" inseam hiking shorts . . . similar to what gymnasts might wear, but different fabric and having pockets. Most of these guys were "retired-age", but not overly flabby. Still, although their shorts were "native" to them, they tended to look a little out of place over here. I highly suspect there were not freeballing (for various reasons).
A few years ago, I saw a mid-30ish guy and his wife. He had a pair of denim cut-offs that were about 1" above mid-thigh on him (he was about 5'9" or so) as they walked into Office Depot. While not muscle-bound, he wasn't flabby either. Slight tan and some body hair on his legs. White t-shirt and running shoes, too. It was like a blast from the past and made me wonder why more guys don't take up that look and woo the ladies (or otherwise) that way. Show some leg!
Enjoy!
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