Quote:
Originally Posted by
SkinnyGoomba 
I've never actually seem a restaurant put "upscale trendy" as their dress code, but I dine out a lot and i'm 25, so I'll voice my opinion.
Yesterday: Upscale steak house, about on par or nicer then Ruth Chris but not Charlie Palmers.
RRL selvage jeans, RL penny loafers, flannel shirt and a tweed sportcoat.
I was middle of the road, some wore suits some wore sweaters and jeans, some wore turtlenecks and sportcoats.
Upscale Restaurants in a city:
I'll wear a suit and tie, sportcoat and slacks or a sportcoat and jeans depending on where i am and who i'm with.
More important than what you wearing is knowing how to act and how to order. I'm working on my wines still.
The places I like to go have a wonderful way of staring at you like your trash if you're under dressed, its a good litmus test.
Ahh...I actually have some thoughts on this. I happen to work as a waiter at one of the best restaurants in Sydney, and my collegues and I are all professional enough to make any dude, no matter how well dressed, look like a douche in front of his date. So I'm glad you realise the importance of knowing how to order or conduct yourself in front of your waiter and your date.
1. Know your wines, but don't flaunt your wine knowledge. Chances are the waiter would know more about it than you. It's their job.
2. Don't take forever with the menu. It'll make you look like you have no idea.
3. When the waiter brings the wine to the table and offer you to try it, try it if you feel like it, but only if it's a bottle with a cork. You won't need to with screw caps as they're almost never off.
When you try it, FFS don't swirl it around like crazy, you don't want to spill it. When you give the go-ahead don't say the wine tastes good as you're not tasting it to see if it's good then you'll have it, you're tasting it to see if it's off. Chances are it's not, so just give the waiter a nod or a quick wink is what I usually do.
Last night I went out with my mate and his father to an Italian place and I know jack-all about Italian cuisine. So I didn't even bother to look at the menu and I just got the waitress to order an entree and a main for me, and got her to bring the most expensive bottle (safe in the knowledge they don't have a cellar list

) of riesling. What happened afterwards in a dark back alley close to home, you can click on the link a couple of posts up.