How to dress for "upscale trendy" restaurant?

Navy blue suit.

What city are you in?

the only risk is your jeans. if the date is important I would call the restaurant

Go there a night or two before your date and check out the crowd.

Twotone

A bit too much work

Slacks and a sweater

Usually that is just code for "with money, wear anything and we'll call it trendy".

Yes, this depends on where you are located.

I don't go to restaurants that have a dress code that is "upscale trendy", it sounds like some awful Vegas joint.

I worry more about food stains than anything else when dining out. With that in mind, remember to minimize accidents by avoiding (if possible) pasta, red wine, or anything else that will stain, squirt, spill, roll or splatter. A darker striped shirt is a suggestion. Black shoes/boots if possible, for the same reason. I agree with your dark jacket. Since I'm not an expert on denim, I'll stay out of that area. Were it me, I would wear dark green, tope or rust colored cords (narrow leg). What makes for 'trendy' more than anything else (in my opinion) isn't just what one is wearing, but that we are having fun with the company we keep. Laughs, smiles, and looking into each others eyes, show you are enjoying each other, and life in general. To others in the restuarant, you'll be seen as a very handsome 'trendy' group. Bon Appetite, and take pictures.

"Food stains" ==> "patina"


Problem solved.

If it were that easy... the cost of food...

can you imagine:
Wow the deep redness in your cordovan
its marinara.

Birthday suit. You will be so trendy that you'll be ahead of the curve.

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.

Which Outback Steak House is this?