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Step 1
Measure. Bermuda fashion tradition calls for Bermuda shorts to be worn three inches above the knee on men. Make sure the shorts are pressed and that you don't carry bulky items in the pockets so the legs hang straight down without puffing. Ladies have a lot more leeway on length and style and can pretty much make a personal fashion choice with the shorts.
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Step 2
Go dressy. Bermuda shorts were originally designed as part a dress uniform. If you're in Bermuda or one of the close neighboring islands of former British rule, wear the shorts as part of a dress attire. Pick out brown or black loafers to wear with long Bermuda socks, a navy blue or black blazer and a shirt and tie.
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Step 3
Pay attention to footwear. If you're not wearing Bermuda dress attire then you should pay careful attention to shoes to wear with the shorts. European inspired visions of dark socks with sandals will draw laughs in the Caribbean. Instead, try flip-flops or, if you want a closed toe, wear some Converse "Chucks" with low-riding socks or none at all to make the shorts look good.
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Step 4
Tone down the shirt. Unless you're dressing up as Magnum, P.I., for a costume party, resist the temptation to wear an outlandish Hawaiian shirt with Bermuda shorts. Loud Hawaiian shirts will make you look like a super-tourist. Instead, find a nicely cut, but somewhat mellow, button-down shirt. Leave two or three of the top buttons open. Or, if you want a bit more style, throw on an undershirt and leave the button-down completely open.











