Help! What do I wear to have dinner with new boss?

[Anonymous]

Changing jobs and start in a few weeks. New boss and another coworker invited me out to dinner the night before I officially start. We’re all women. The restaurant is a nice one, not casual but not super fancy in Manhattan.

I haven’t worked in an office for years let alone had a business dinner like this. I also just lost 30 pounds and nothing fits.

Do I wear a dress? Slacks? What Id wear to the office?

Please give suggestions. I’m at a total loss

[Anonymous]

How much are you prepared to spend?

[Anonymous]

Anonymous wrote:How much are you prepared to spend?

This is a senior exec role. I’ll spend what I need to.

[Anonymous]

I would just wear nice black pants, a silk blouse, and heels. And then for the "polish" I would focus on a blowout, makeup being on point, and good jewelry/purse.

[Anonymous]

I think you should go with a shift dress, with fun jewelry (to indicate you know it's not work time). Like this in navy or black, with colorful cardigan and jewelry. Then you can wear it to work with more subdued accessories and heels.

https://www.quince.com/women/wool-sleeveless-dress?color=grey-melange&gender=women&tracker=collection_page__%2Fwomen%2Fdresses__All%20Products__7

[Anonymous]

Either of the PPs’ suggestions are a good way to go.

[Anonymous]

That grey shift dress is a knockoff of a Theory dress that I wear to the office when I don’t have anyone to impress. I think it’s too bland. For a dinner meeting, I would do a navy or black high quality dress and jacket, but with some color either in jewelry or a scarf. This is not dinner, it’s the end of your interview process—it will set the tone for how you’re received. And then be professional but jovial. Good luck and congrats!

[Anonymous]

Professional wear, I’d do a dress with a blazer and simple elegant earrings.

[Anonymous]

Just as long as it's not slacks or a pant suit. oof! So boomerish.

Also, dressing nicer than the boss could backfire.

[Anonymous]

Are they coming from work?
Don't look overdressed or over fussy.

[Anonymous]

Anonymous wrote:Professional wear, I’d do a dress with a blazer and simple elegant earrings.

Absolutely this.

[Anonymous]

I think it depends what the daily wear in the office is. In NYC people dress a lot more interestingly than in DC.

If the office is very stuffy I guess play it safe with a blazer and dress. But if women wear a variety of things I would do a slightly less formal midi dress and nice boots, high end jewelry so you can be a little more relaxed and get to know each other.

https://www.nordstrom.com/s/theodora-ruched-long-sleeve-midi-dress/8573547?origin=category-personalizedsort&breadcrumb=Home%2FWomen%2FClothing%2FDresses&color=052

[Anonymous]

Anonymous wrote:I think it depends what the daily wear in the office is. In NYC people dress a lot more interestingly than in DC.

If the office is very stuffy I guess play it safe with a blazer and dress. But if women wear a variety of things I would do a slightly less formal midi dress and nice boots, high end jewelry so you can be a little more relaxed and get to know each other.

https://www.nordstrom.com/s/theodora-ruched-long-sleeve-midi-dress/8573547?origin=category-personalizedsort&breadcrumb=Home%2FWomen%2FClothing%2FDresses&color=052

https://thefoldlondon.com/product/savoia-merino-dress-deep-maroon/

[Anonymous]

The last two dresses are both pretty good. i think shift dress and blazer is fine but boring for dinner. That's more interview wear.

the grey quince dress is hideous.