Update: Okay, here's what I think I'm gonna wear: 1) Black Hugo Boss Jeans - these are really cool pair of jeans I have that are semi shiney, but not pretentious 2) Casual gray striped white shirt 3) Black oxford sneakers and socks. 4) Dark Gray vest. And I plan to roll up my sleeves... Cool or not cool? _______ It's a first date, I barely know the guy. Met online because I posted a message saying I wanted to hang out with folks since I'm new in town. He happens to be new in town as well. We're going to a casual/contemporary Italian restaurant, and I was thinking of wearing the following: 1) Brown corduroy pants, 2) Casual gray striped white shirt, 3) Light to dark vest, 4) Black oxford sneaker, 5) Black socks So, is that okay? Do you think it'll be too pretentious? Shall I wear Black jeans instead? I'm worried that I'll look too dressed up for a casual place, but then again do I pull a first date outfit and wear a black valvet blazed with a crisp white shirt and a black jeans?