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I'd say wear pants for the first date. You don't know if she's going to dress up a little bit. Women can look a little dressier in shorts than men, so if she wears shorts and you're wearing jeans, that still looks okay. But if she's wearing something nice and you're in shorts and a polo shirt, she's going to feel overdressed.
As far as acceptable shoes with shorts go, leather flip flops are okay if your feet are in good shape. No sandals with socks. No visible socks in any kind of shoes with shorts. Get socks that don't show. Sneakers like converse are okay, athletic sneakers may look weird.
I don't know about a restaurant unless it's a very casual one, or an outdoor cafe or something, but sure, shorts should be fine. Choose a long pair (just below the knee) and make them nice...like new khakis.
I'd avoid flip flops under any circumstance except perhaps meeting at the beach.
I'd say wear pants for the first date. You don't know if she's going to dress up a little bit. Women can look a little dressier in shorts than men, so if she wears shorts and you're wearing jeans, that still looks okay. But if she's wearing something nice and you're in shorts and a polo shirt, she's going to feel overdressed.
Ok I'm leaning toward that to be on the safe side.
Quote:
Originally Posted by Hedgehog_Mom
As far as acceptable shoes with shorts go, leather flip flops are okay if your feet are in good shape. No sandals with socks. No visible socks in any kind of shoes with shorts. Get socks that don't show. Sneakers like converse are okay, athletic sneakers may look weird.
Now assuming I wear jeans and a polo, could a nice pair of sneakers be acceptable? I have loafers but they are kinda heavy and I'm not sure they will match my gray top (shoes are brown).
I don't know about a restaurant unless it's a very casual one, or an outdoor cafe or something, but sure, shorts should be fine. Choose a long pair (just below the knee) and make them nice...like new khakis.
I'd avoid flip flops under any circumstance except perhaps meeting at the beach.
We won't be meeting at the beach so that's out. Speaking of shorts, what do you think of black flat front shorts to wear in general? Almost picked some up the other day
Now assuming I wear jeans and a polo, could a nice pair of sneakers be acceptable? I have loafers but they are kinda heavy and I'm not sure they will match my gray top (shoes are brown).
Sneakers and jeans are fine together.
It's just shorts that run into those weird shoe/sock issues.
On the first date, she's probably going to be bringing her A-game clothes-wise, so you should do the same. Save the shorts and flip-flops for later.
Sounds like a plan!
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Speaking of shorts, what do you think of black flat front shorts to wear in general? Almost picked some up the other day
