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Opinion on loafers with shorts

I'll post a picture below, but today on my vacation I wore a pair of black loafers with some light, almost white khaki shorts and a plain black t-shirt. A female companion laughed at me and said the loafers look stupid with the shorts as they are too dressy, but I thought they looked pretty sharp with the crisp khaki shorts, almost like a slightly more grown-up way of wearing Sperry Topsiders. Sitting here insanely self conscious about it because I had no idea it was perceived any other way. Please let me know who is right. The shoes are the Prescotts by Bostonian.
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These are leather, though. And I'll admit they are shiny and can be dressy but I thought with some crisp white shorts they looked dapper.
 
If you happen to be away on vacation, don't let it bother you, no one is expected to have an entire wardrobe at their disposal.

While I do not like the way the lady went about telling you here opinion (teenager reaction), I do have to side with her.

If you are going casual, go casual all the way, those are too dressy.
 
It really doesn't work - the little metal parts on the side make them look way too dressy for shorts.

+1 ... and they are too shiny.
And going sockless with that style of shoe doesn't seem to match up.

Get yourself a pair of cheap sneakers at a local shoe store.
 
I wear shorts with fancy moccasins but never with penny loafers. Bermuda shorts, knee-high socks, and nice leather shoes (including penny loafers) are considered business and even formal attire in...Bermuda.
 
I wouldn't wear black loafers with shorts although it might work ok.

I lean toward cordovan, penny loafers or semi-gloss, brown, bit loafers with shorts and jeans. However, I think semi-gloss, black, bit loafers would be fine with some shorts and jeans also.

Ron I
 

Doc4

Stumpy in cold weather
Staff member
IMHO they only work if you go "full Bermuda" ...

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... but if you do please ... please ... please wear socks.
 
Visually, the tongue and the gore look too high on the OP's foot: up at the ankle instead of lower over the arch. On the Bermuda-Shorted gentlemen, above, the tongue is high, but the gore is lower. I think this is a more casual look than the less casual look of the OP's shoes. I think Penny Loafers, Tassel Loafers, and even Tasseled Kiltie loafers can be worn with shorts (and without socks) if the slip-ons are cobbled low enough on the foot. As always, just my opinion.


Tom
 
This may be the trick to pulligg off pairing loafers with shorts. IMHO the suede material says casual and so it's a better match to the more casual shorts attire.

Tim
 
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ouch

Stjynnkii membörd dummpsjterd
My whole family were loafers.

 
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Forget about what we think -- the more important thing is what the ladies think, and your friend's laughter, while slightly cruel, was ultimately doing you a favor by doing it to your face instead of inwardly or worse, laughing behind your back at your sartorial stumble with other ladies. There are plenty of styles of inexpensive and stylish canvas shoes out there, so why try to swim upstream on this one?
 

musicman1951

three-tu-tu, three-tu-tu
They're fine. I wouldn't wear them that way, but they are not incorrect. I would prefer penny or suede, something less dressy. But that's just me. This is not life and death stuff - especially on vacation.
 
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