I have some Sperry moccasins that I wear with no socks and shorts. It seems to work for me.

Regards

"The trouble with our liberal friends is not that they're ignorant, it's just that they know so much that isn't so." - Ronald Reagan
 

I've also seen it done with bit loafers. Also, make sure you're white and look waspy (i.e. no jew fro). The look you're going for can really only be pulled off by very white people, just saying...

 

I am not white and I pull this regularly. Penny loafers, bit loafers, driving mocs, Sperrys, even tassel loafers (if you even own those monstrosities) without socks is a classic look.

As a rule of thumb, unless you're playing sports you oughtn't to be wearing socks with shorts. i.e. The masses walking around in low-cut socks with Vans and cargoes on need to learn how to dress like an adult.

I am permanently behind on PMs, it's not personal.
 
Best Response

Shorts with sockless loafers is a great summer look (also much cooler than wearing socks). Its more about colour and what your shorts / rest of what you're wearing looks like than the brand of the shoe. Make sure your shorts are more fitted and not supper baggy with cargo pockets as your shoes won't be as bulky as the sneakers you might be used to wearing with shorts.

As for the type of shoes, it could work easily with driving shoes, boat shoes or most slip-ons that don't have massive heels (materials don't matter either, suede, leather, etc...). I usually wear driving shoes when wearing shorts but boat shoes work as well. Converse high tops work with shorts also, but are a more urban look.

Make sure you don't wear the same pair two days in a row and use a shoe tree once they've dried after wearing. This is good advice generally, but is particularly important if you're going sockless as the shoes are in direct contact with your feet.

Note: You don't need to be "white" or "Waspy" or any other stereotype to wear sockless shoes with shorts. Anyone can do it and its a look you see all over Europe, Latin America and Asia. I've even seen people in NYC pull it off with brogues and lace ups (although its much more of a fashion statement)...

 

Barney - that was my question exactly. I'm buying some new shit and was browsing style forum and some other nonsense and the look was getting torn apart. I think it's pretty legit, so I wanted to check here as opposed to getting the hipsters' opinions on rocking sweet keds with torn jean shorts on those sites. I have some of the Sperry Gold Cup topsiders (here On sale!) but wanted some penny loafers and didn't know if nice Ferragamo's/Prada were too "elite"/asshole looking.

 
jos.a.bankhard:
Barney - that was my question exactly. I'm buying some new shit and was browsing style forum and some other nonsense and the look was getting torn apart. I think it's pretty legit, so I wanted to check here as opposed to getting the hipsters' opinions on rocking sweet keds with torn jean shorts on those sites. I have some of the Sperry Gold Cup topsiders (here On sale!) but wanted some penny loafers and didn't know if nice Ferragamo's/Prada were too "elite"/asshole looking.
the shoes you linked to look ok to wear sockless with shorts. Especially if you're wearing an Oxford cloth button down shirt or something with your shorts.

What kind of Ferragamos and Prada's were you thinking of? Most work well depending on what you pair them with.

 
jos.a.bankhard:
Barney - that was my question exactly. I'm buying some new shit and was browsing style forum and some other nonsense and the look was getting torn apart. I think it's pretty legit, so I wanted to check here as opposed to getting the hipsters' opinions on rocking sweet keds with torn jean shorts on those sites. I have some of the Sperry Gold Cup topsiders (here On sale!) but wanted some penny loafers and didn't know if nice Ferragamo's/Prada were too "elite"/asshole looking.
That would get torn apart on Styleforum because the Men's Clothing forum runs very far on the trad side and the sockless shoes with tailored shorts look is quintessential prep. That forum doesn't believe in wearing shorts, period, so no surprise that you got lit into. The Streetwear section is too edgy for me, don't know if you went in there.
I am permanently behind on PMs, it's not personal.
 
jos.a.bankhard:
Barney - that was my question exactly. I'm buying some new shit and was browsing style forum and some other nonsense and the look was getting torn apart. I think it's pretty legit, so I wanted to check here as opposed to getting the hipsters' opinions on rocking sweet keds with torn jean shorts on those sites. I have some of the Sperry Gold Cup topsiders (here On sale!) but wanted some penny loafers and didn't know if nice Ferragamo's/Prada were too "elite"/asshole looking.
Go to Mr. Porter and then scroll over (or click on) the different shorts they have and there's an outfit view of each. A lot of these looks are definitely high taste as Mr. Porter carries all of the luxury brands you're talking about and more that you've probably never heard of before.

You should be able to get a good sense of what type of shoes/shorts/outfit combinations work. Like if your buying cargo shorts, then obviously loafers would not work with that etc...

 

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