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@KatNYC2011: You could always call the restuarant and see what attire people usually wear and then go from there. 
Good luck!
I would probably do a black wrap dress, tights, boots and fun jewellery.
I have also done dark skinny jeans with heels, a fun top, cool jewellery and a boyfriend and still felt dressy enough.
Never underestimate the power of a little black dress. I have a knee length Ann Taylor cowl neck dress that is my go-to for nice dinners out. Pair with a brightly colored scarf, pumps, and a pea coat and have fun!
I think you'd be fine with really dark jeans and a cute top/sweater and killer boots/shoes
I don't think it will be too cold to wear a nice but not too formal dress, with a pair of pantyhose. Just pair it with a warm peacoat, and a clutch and you'll be good to go.
@Cash000: The bigger issue is that there is a LONG walk from the tube to the restaurant and it's right on a river so there will be wind making it colder.
Also, since the walk is long I'm going to try and avoid heels since I'm terrible at walking long distances in them.
I want to avoid jeans because I don't feel like they are appropriate for the occasion since both DH and his boss will be in suits from work.
What field is your DH in? Will your DH and his boss be coming directly from the office? That would influence what I would wear. If they will be in business attire, I would wear a LBD possibly paired with a jacket or a pantsuit with a brightly colored top underneath.
ETA We were posting at the same time.
Black pants, and a cute top? You'll look fabulous in whatever you choose! :) Good luck with the dinner!
@GroovyHippieChick: I'm making this difficult aren't I!?
I just asked DH and he said that dress pants with a "fun" top would probably be fine.
Hmmm... now I have to figure out if I have a "fun" top.
I guess I could also go with dress pants and a black top and fun jewlery.
I have a "back up" outfit but it feels really business like.
Grey wool trousers, black button down shirt, big chunky gold necklace, and fun colorful gold patterned bracelet (also big).
I'll have to dig in my closet to see if I have a better top though.
It didn't used to be this hard when I was having to put together outfits for work every day, I'm just SO out of practice!
Personally, I'd wear thick black leggings and a nice dress dark coloured but not black, smart coat and some understated jewellry. With flat boots. And a long winter coat and scarf.
But, if that's out I always think a lighter coloured trouser/pant looks less "work-wear" than black. Match it with a nice bright blouse (not too formal or you'll be in the work wear catorgory again).
I think the other issue is that I have definitely had some newlywed weight gain, so I don't feel as comfortable in my "cute" clothes.
@ladyartichoke: Thanks! At least I do have a suitable backup. That makes me feel a bit better.
Nice business casual dress is my suggestion. I just went out to dinner with mf FI's boss (met her the first time that night) and wore: Black panks, black boots (there was snow on the ground - nice ones but high heeled ones which might be more suitable to clubbing), grey cashmere sweater and low key jewelry. If you can skip button down shirts (a little *too* stuffy work attire), I'd suggest that, but I could have easily worn any number of work appropriate tops - just make sure to keep it more "work" than "clubbing" attire, and dress it up with some jewelry (although don't go over the top on that, keep it tasteful). A scarf you're a scarf person could dress it up too. LBD if it wasn't cold out would also work in the future.
ETA: It's not unreasonable to look work-like. You very well could be coming from work after all for dinner!
@KatNYC2011: nah, you're not difficult! I just like crossing things out in my head. lol
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Beekeeper
I have dinner tonight at a nice restaurant with DH, his boss and his boss's wife.
Since moving here I've been living in either casual clothes or my interview suit depending on the day.
We're going to a really nice restaurant and I have NO idea what to wear. I feel so out of practice!
It's going to be cold tonight (around 40F) so I feel like I need to wear pants so I don't freeze.
I just am not sure how to do a nice pants outfit that doesn't just look like business or work wear.
Any help from the fashion forward bees?