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I'm not talking the cheap rubber or Old Navy flip flops, but a nice pair of leather flip flops or sandals paired with khaki shorts and either a button down or polo shirt. Let's assume the feet are in decent shape.
As for the location of the date, let's say a casual restaurant, outdoor bar, coffee shop, or the like.
I never thought this would be an acceptable outfit but had a conversation with a female friend who considered that a dressy outfit and acceptable, which surprised me.
What do you think? Could that be considered a dressy outfit or too casual for a first date?
I would not be offended in the least. As long as his feet aren't gross and his clothes are clean and not wrinkly! Especially in the summer I would prefer this outfit to someone who was sweaty because they were too hot! That being said I dress pretty casually most of the time.
With my wife of 22 years? Sometimes. If I'm casual though my clothes would still be pressed with a nice pair of sandals. I hate flip flops and only got used to wearing sandals since I moved to TX 12 years ago. If I was dating? Hell no, even though it would be perfectly acceptable where I live.
Probably not unless he chews tobacco, wears ball cap front or backwards with the flip flops. The next step for evaluation is: when he parks, does he pull through to the empty slot in front (means he thinks ahead), and does he pick up dog do-doo, even if no one is around (considerate).
The Diss wears shorts? That's something I might like to see. Actually, after so much hand-wringing on the forum, I'd like to see The Diss in cool, comfortable, enjoyment mode in general. I think, after the wedding we should have a big barbecue for The Diss, and have a nice, mellow hang-out, get to know him, and wish him the best for the future. Could be fun.
I don't do weddings and funerals. But if this goes down in Loo'ville, I'm the afterparty.
I'm not worried about being "dressy" in Virginia heat and humidity in July. I'm worried about being comfortable. Hopefully most women with sense would not be that harsh to judge over a very presentable choice in clothes that is season appopriate.
I agree, it depends on the weather. If the weather is hot enough, if a guy has some decent shorts and a shirt, maybe some Birkis, if his hair is good, beard, if present, is shaped up, what's wrong with that?
In parts of the hot, humid South, this time of year, you kind of need to dress for maximum cooling effect, or you will be a sweaty mess pretty quick. At least that's how it worked for me.
I would expect a first date to want to make a good first impression and flip flops do not make a good impression. Flip flops are for lounging around the house, running errands or hanging out on the beach.
I agree, it depends on the weather. If the weather is hot enough, if a guy has some decent shorts and a shirt, maybe some Birkis, if his hair is good, beard, if present, is shaped up, what's wrong with that?
In parts of the hot, humid South, this time of year, you kind of need to dress for maximum cooling effect, or you will be a sweaty mess pretty quick. At least that's how it worked for me.
I think the cultural expectations down here reflect this as well. At least in Raleigh, there are probably only a handful of places where a polo/button down with shorts in the summer wouldn't be dressy enough. Any casual restaurant that tried to have a dress code like that would go out of business in less than a month.
The sandals thing is a little more questionable. It's really not my style, so I don't know what the etiquette is around that.
First... is this an actual date... or just the first time you've met.
Assuming the latter it's a 15-30 minute time out during a day for a coffee etc. Right?
Then sure... dressing casual is fine.
otoh... if it's an actual date and you're going to a casual spot...
then sure... dressing casual is fine.
Both - it's a lunch date at a casual restaurant
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That's something I might like to see. 
Actually, after so much hand-wringing on the forum, I'd like to see The Diss in cool, comfortable, enjoyment mode in general. I think, after the wedding 
we should have a big barbecue for The Diss, and have a nice, mellow hang-out, get to know him, and wish him the best for the future. Could be fun.
