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What type of shoes do guys wear with shorts?

OluKai Manini sandal flip flops.

$Oulaki Sandals.jpg
 
Either sandals or tennis shoes. I don't like wearing shoes with shorts, is like wearing a sports coat with shorts, it may look cool in Nantucket, but not in my world:laugh:
 
Are birkenstocks the shoes that mold to your feet over time? Their insole will slowly shape to the form of your foot?
I thought I heard that from someone once.

I believe so - they have a cork footbed that can feel firm, but they do fit my feet and have a nice feel. Naots are similar in that respect. The problem is that I have a narrow "B" width foot, which rules out much of what both companies make.
 
Are birkenstocks the shoes that mold to your feet over time? Their insole will slowly shape to the form of your foot?
I thought I heard that from someone once.
I have a pair of Betula (by Birkenstock). They have a preformed/preshaped foot bed made from cork that should conform a little more over time to your exact foot shape, while also providing sturdy support. I don't wear mine very often due to lack of heal strap, I mostly wear them at the height of summer (July/August/September) and then only a few hours at a time. Since I do not like wearing flip-flops or similar style shoes without the help of a heel strap. But they remain in my closet because of the very nice footbed and comfortable feel. If you like flip-flops I think you will like them a lot.
 
Keen has a few styles of canvas shoes that would most probably fit your bill.

Yeah...I love my Keens.

No, I'm not a paid shill.
 
Lose the cargo pockets and get shorts that are actual shorts - not cropped baggy pants that end around your calf.

Khaki, faded red, seersucker, madras or plaid shorts that end just above your knees - an inch or two is correct. If you find a pair you like that are too long, spend the couple of bucks to have the tailor hem them to the proper length for you. These shorts will go with anything; polos, tee shirts and casual button downs.

Shoes are easy: boat shoes, penny loafers or (if you are balls out preppy) white or dirty bucks. Under no circumstances are socks to be worn with any of those - even the bucks

Flip flops are for the beach, if you are in social situations you are better off with the options listed above.
+1. To which I add canvas slip-ons/espadrilles and, if you are even more balls out preppy, saddle shoes.
 

Rudy Vey

Shaving baby skin and turkey necks
When I visited South Africa some 20 years ago, some of the Boers wore shorts with long wool socks and high boots, looked good on them. Most of them also carried a gun on their belt and a wide brimmed hat.
 
If it's warm enough for shorts, typically I wear flip flops or sandals. But sometimes I'll wear boat shoes; I have several pairs of all 3 types.
 
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