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Those are not shorty shorts by any stretch of the imagination.
They are too high above the knee for my taste. But you're right, I've seen shorter. And I'm sure others think they're fine. I like men's shorts at or just above the knee line like this.... Men’s Golf, Chino and Cargo Shorts from Ralph Lauren
Just to clarify... I think men should wear no-show or very low sport ankle socks (e.g. Nike, Under Armour) with tennis shoes and sport shorts ONLY when they are playing sports or running. Otherwise, their shoes would stink and they'd get blisters. I also think it is ok if a guy wears taller crew socks for certain sports (e.g. black crew with basketball shorts).
If a man is not playing sports, I prefer he wear dress shorts with good loafers, sandals or topsiders and NO SOCKS.
I can not picture how pushed down tube socks could ever look good.
I live in Florida and have seen every imaginable combination of shorts and footware and in my opinion, shorts with loafers is the most ridiculous and pretentious. Sandals will ruin your feet (take it from someone who wore them for years) unless you want to wear Birkenstocks (which I wouldn't be caught dead in btw) and topsiders just flat out smell bad. At least the old guys with their oxfords and black nylon tube socks have a comical quality that can't be beat.
I wear Van's HalfCabs and ankle socks exclusively when I'm wearing shorts, but the pushed down crews would work too.
i wouldnt be caught dead wearing those R Laurens. I look at shorts like those and i picture someone like William Zabka from an old 80s movie with a popped collar on a polo shirt. Besides, "Chinos"? Sounds like they should come with a green card.
Sorry Nightcrawler but a California boy is never going to take fashion advice from a New Yawker. When I was a kid you were the folks who wore dark socks and leather shoes with your loud bermuda shorts and ban-lon shirts.
Back to the original question, id say wear what feels comfortable to you and doesnt get you teased. Go to a store and ask one of the sales clerks what the latest style is. heck just look at other people wearing shorts. Whatever the majority is among people your age group go with that.
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