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What type of shoes do guys wear with shorts?

I'm actually a big fan of the "cowboy boots with shorts" look.

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Is she wearing boots? Oh yeah, I guess she is.
 
Hiking boots.

Comfort of athletic shoes without the look of being 8.

I wouldn't make it far in those canvas shoes before my feet just fell off.
 

Toothpick

Needs milk and a bidet!
Staff member
I would have never thought hiking boots & shorts would be a match. interesting.
 

Doc4

Stumpy in cold weather
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... okay, maybe not the look I'll try to pull off.

Personally, I'd go for Vibram 5fingers (or you may like sandals of one sort or another). If not, a casual non-leather-but-still-natural (eg canvas) shoe like the boat-shoe crossover types seen above ... or a boat shoe or desert boot.
 
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.

You must be in a different part of Massachusetts than I. Pretty sure I have never seen a pair of white bucks in the city. Believe it or not, I had to explain what seersucker is yesterday. Strictly speaking dirty bucks are worn in whiskey season, white bucks in gin season.

When I can't be barefoot, it's crocs.

Crocs ... shoes ... same sentence!

"Flip flops are for the beach, if you are in social situations you are better off with the options listed above"

Well....maybe up there in Mass., but then I'm kind of fuzzy on the "social situation" thing, whatever that may be.

Nonetheless, I live on the beach (about 600 yards from the mean high tide line). Flip flops (the cool ones-Reef, Sperry, Sanuk, or a one-off artisan version for the tragically hip) are worn here for any occasion. Church, court, funerals, bar hopping, weddings, school, work. Probably even get away with wearing them to some job interviews here.
Joys of tropical living..although there are better venues in which to exist.

While wearing shorts and flip flops might be acceptable in some of those situations, I'm not certain I'd feel comfortable doing so.
 
I love my Choco sandals

I just picked up some Bedrocks

but I also wear NB minimuses pretty often. if my ankles hurt, I'll rock my Asolo Fugative GTXs

for me, shorts is about casual and comfortable. if you don't like me while I'm comfortable, or will hold it against me, we may not be best suited towards friendship anyway.

if I cared about my footwear to the degree you seem to be for the occasion, I'd also transition to a lightweight/cool pant. I haven't worn boat shoes since high school. not bad, but... my feet are too big to look good in driving mocs, to me.
 
The sound of flip-flops makes me want to take a 9 iron to the Achilles tendon of the wearer, not to mention the fact that you have to walk with a feminine stride to keep them on your feet. Ankle high leather sandals or hiking boots in a nice design go well with shorts IMO.
 
Good thing with boat shoes and canvas sneakers is that even in the transitional months when you may not have to wear shorts, you can still wear them with jeans or chinos or any casual long pant without socks and they will still serve you well. I would suggest using a little talcum powder to keep your feet dry if you are going no socks, or at least something to keep the smell down in between uses.
 

Toothpick

Needs milk and a bidet!
Staff member
Good thing with boat shoes and canvas sneakers is that even in the transitional months when you may not have to wear shorts, you can still wear them with jeans or chinos or any casual long pant without socks and they will still serve you well. I would suggest using a little talcum powder to keep your feet dry if you are going no socks, or at least something to keep the smell down in between uses.
goldbond foot powder!
 
professional and short don't mix in my mind.
I wear what I damn well please according to my fashion sense and the situation.
Shorts, my khakis, I wear my Margaritaville beach shoes, moccasins, or sneakers.
 
The sound of flip-flops makes me want to take a 9 iron to the Achilles tendon of the wearer, not to mention the fact that you have to walk with a feminine stride to keep them on your feet.

Do what?!

You sound pretty bad at wearing flip flops. I could run a 100M in mine fairly easily.
 
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