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Discussion Starter · #1 ·
I'm not normally the type to wear shorts. However, I broke down and bought a khaki pair that fit well. They come to right below the knee so I suppose technically they're Bermuda shorts.

What sort of footwear do I wear with them? The most obvious thing in my wardrobe are a pair of brown car shoes. I have some Alden deck shoes but they have a tear in the leather and my local repair place recommended sending them back to Alden.

If I were still in high school I could get away with wearing dirty bucks or brown and beige spectators, but this isn't the 80s.
 

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I prefer about a 7” inseam on my shorts. What you’ve described sounds like 11”+. I echo the suggestion of taking them up to above the knee, lest they get mistaken for capri pants.

As for shoes, many good suggestions already given. For me, it’s flip-flops, top-siders, drivers, or camp mocs. There are a number of plain, low-profile sneakers on the market right now, too, as those have become very popular to wear with just about everything (unfortunately). With shorts, though, they’d actually be appropriate.
 

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Discussion Starter · #7 ·
OK, I tried them on - they're just above the knee, not below. The last pair of shorts I owned were for jogging and they were significantly and awkwardly shorter.

I suggested the drivers because my boat shoes are damaged, and a neighbor has made driving shoes and shorts his warm-weather uniform. Coupled with a plastic cup which may or may not be filled with bourbon, but I digress.

I'll try the boat shoes when the weather warms up later this week. If I like the look I'll get them repaired. Otherwise I'll do the dirty bucks and short socks. Thanks everyone!
 

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I'm surprised this is an issue, but here is what I wear with shorts:

Sperry docksiders AO (a few different pairs in different colors/leathers)
LLB mocs
Alden LHS in shell cordovan (I have all three available models: #8 lined, black lined, and BB unlined).
Allen Edmonds Grayson in #8 shell cordovan

To put this image in perspective: I am a well-fed middle aged white man. My shorts are all khakis. My shirts are either LLB polos or BB madras shirts. I occasionally wear a long-sleeve blue oxford with shorts as well.

Cliche, probably.
 

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Usually Topsiders.

But often Techamphibians.

Never with socks.

Used to wear CVOs/plimsolls all the time, laced or slip-on. But they wear out quickly, and are expensive in the long run.

Even when everyone else was doing it, I always thought shiny loafers looked wrong with shorts.
 

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Growing up in the south, I wore shorts in summer well into my 30s. I favored the Sperry line as well as the occasional loafer.

Once I moved overseas, I noticed that the only people wearing shorts were school children, people at the beach or those engaged in sport. I now eschew shorts except for these limited occasions so I no longer face the shorts/footwear issue.

Cheers,

BSR
 

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Growing up in the south, I wore shorts in summer well into my 30s. I favored the Sperry line as well as the occasional loafer.

Once I moved overseas, I noticed that the only people wearing shorts were school children, people at the beach or those engaged in sport. I now eschew shorts except for these limited occasions so I no longer face the shorts/footwear issue.

Cheers,

BSR
Do gentlemen in your circle ever wear longish shorts with knee stockings?
 

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Do gentlemen in your circle ever wear longish shorts with knee stockings?
Culottes? I believe the writer David Sedairis is trying to bring the culotte into style. :)

One exception in my overseas experience was my my Afrikaner friends who favored a very short gym short which looked like something from a 1970's beach film. You could essentially tell Jew from Gentile if you get my meaning.Some hunted in the bush in shorts and sandals. The ticks were horrendous and the acacia trees had spines 3" long. They often looked like they had been flayed alive, but never a complaint was heard.

Cheers,

BSR
 

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Culottes? I believe the writer David Sedairis is trying to bring the culotte into style. :)

One exception in my overseas experience was my my Afrikaner friends who favored a very short gym short which looked like something from a 1970's beach film. You could essentially tell Jew from Gentile if you get my meaning.Some hunted in the bush in shorts and sandals. The ticks were horrendous and the acacia trees had spines 3" long. They often looked like they had been flayed alive, but never a complaint was heard.

Cheers,

BSR
I know the look, also found among white Zimbabweans. And often the shorts are of synthetic material.
 
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