Fancy dinner outing in Boston. Help!

I am gearing up for a work trip to Boston, which will include casual, fancy, and business events. I'm worried about my clothes for all of those, but I am starting with the fancy.

We have a dinner invite which I think will be fancy. Unfortunately, I don't have a restaurant name, but I am fairly confident that it will be an upscale restaurant in Boston's Back Bay.

My options are limited, but I came up with four ideas. Please let me know if I am on the right track with ANY of these, or if I need to go back to the drawing board (sorry about the photo quality, especially on the black outfits! If anything looks promising, I can get better photos posted):

Option 1 is a fairly simple black knit cowl-neck dress with a belt, which I know is hard to see, but I think it might read as more of a "work" look than a dinner look:

http://picasaweb.google.com/ms.....3643283922

Option 2: I like the proportions of this look, but since the shirt is just jersey, I'm worried it isn't fancy/formal enough:

http://picasaweb.google.com/ms.....3247074562

Option 3: This is one of those closet-lurking items that I really thought looked great...until I took a picture of me in it! I think it strikes the right note of "fanciness," but it also seems like it isn't doing me any favors fit-wise:

http://picasaweb.google.com/ms.....6498784738

Option 4: And lastly is a black skirt/shirt combo, which again, I know are hard to see. The shirt has some nice detailing on the front, the skirt is filled with crinkles, and both are slightly more formal than they look in the photo because they are SHINY:

http://picasaweb.google.com/ms.....8708537826

I really appreciate any feedback and constructive criticism on what I should wear to dinner! And don't worry, I promise to accessorize and wear hose when the time comes.

Thank you.

16 years ago

RoseandJoan

Veteran

I really like look 4, I would add a short chunky pearl necklace and black micro fishnets. I like look three but as the formal dinner will still be work related look four gets my vote.

mummy2thea

Active Member

I think outfit #3 or #4 would work best for a formal dinner. Outfit #3 could be dressed up with accessories. I agree with RoseandJoan that chunky pearls would look great with #4.

rute

I prefer option 2 or 3.

Option 1 needs other underwear (we can see the pantie line...).

marianna

I actually really like #3 and I think the photograph may be giving an illusion of awkward fit. It's a really pretty dress and with the right accessories can look amazing. But if you don't feel comfortable in it, #4 seems like the a good fancy dinner option.

shiny

It would be really helpful to know the name of the restaurant. For many of the upscale restaurants here, a simple LBD would suffice, or even smart casual. My gut instinct is this:

Option 1 - good bet, especially since it's a business function. Accessorize with a fun dressy clutch, some micro-fishnets. You may want boots, since it's getting cold here.

Option 2 - Would probably also would work just fine. More of a "safe" choice though.

Option 3 - Gorgeous dress, but I would worry it's too dressy/formal. This is appropriate for a holiday party - is it a holiday party? Might work if you dress it down a bit.... black jacket, boots?

Option 4 - I love the shape of this. Hard to see the fabric in the photo. Can you mix and match? I think this shiny blouse, with a different skirt - one that is matte and not shiny - would strike the PERFECT note.

In fact, if I was going to a business dinner at an upscale back bay restaurant, option 4 is along the lines of what I'd choose: simple black wool pencil skirt, with a shiny silk blouse. Probably go with boots because as I said, it's getting cold here. Do you have a long string of pearls to give it a pop of white? And, you need a clutch.

Melissa

You guys are the best. Thank you so much for the helpful comments!

The option 1 dress is going back to the store--after sitting with it a few days, I realized that I just do not like the sleeves on it.

I think option 4 is looking like the best bet, although I am planning to accessorize and photograph option 3 as well to help me visualize.

@shiny I'll see what I can dig up, but the shiny skirt might be my only workable option. Thank you for the timely reminders that I need a clutch and pearls! I'm going home this weekend, and I totally would have forgotten those necessities otherwise. I still don't know what restaurant we are going to, but if it helps, it is likely to be something along the lines of The Capital Grille or Aquitaine (South End), which I guess is somewhere between mid- and upscale.

Anyway, I'll post some pictures once I have everything in one place and accessorized.

Carole

Since I'm so new to this I don't have tons of confidence, but I thought since you were so kind to help me, I should at least let you know that I like #3 and #4 the best, and when you add the accessories as suggested by others, you will look great!

Steph

I totally agree with Shiny's assessment. My concern would be that you don't want to go too dressy. I think that outfit number 3 would look too dressed up. It's hard to tell if outfit number 4 might be a little too dressy as well, with the two shiny pieces together, because the lighting in the photo isn't ideal. I actually think that outfit number 2 would be perfectly appropriate. Or would it be possible to pair the shirt with outfit 4 with the skirt from outfit 2?

I know Aquitaine well. (Capital Grille, not so much - not a big steak eater). I think Steph's suggestion of blouse in #4 with skirt in #2 is perfect. You want to aim for super-smart, urban, upscale casual. Capital Grille is on Newbury, which is the trendy upscale shopping area, whereas South End is also a trendy upscale neighborhood.

If you end up at Aquitaine, be sure to swing through the Mills Gallery, and (if it happens to be open to the public), the Cyclorama. Beehive is a great place for a drink before/after.

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