What should I wear to dinner w boss?

[Anonymous]

I’m meeting my boss for the first time in person next month because he’ll be traveling to my location for the first time since covid. I’m the only direct report of his in my location so it will just be the two of us. I’m fully remote, and in tech so my go to outfits are much more casual than I’d like to admit. And our office environment is purely casual (people wear jeans and sweatshirts). I want to look nice but fit the occasion (going to a restaurant) without appearing like I’m dressing up for him or anything weird like that.

Please help! O and I’m 34 if age matters in outfit selection.

[Anonymous]

Pants and a blazer

[Anonymous]

Business casual. Something like black pants and a nice sweater or blouse.

[Anonymous]

Dress for the way that you want him to percieve you and how you want the relationship to go.

If you want or have a very formal relationship then a traditional business outfit (think suit). If you already have a more casual relationship or you want to develop a more casual relationship then dress for "Friday at the office." I think you should consider the relationship before the outfit because people will react accordingly - it sets the tone.

Best of luck!

[Anonymous]

How old is the boss and what is his background (tech, law, etc)? What's the vibe of the office (if you know)?

[Anonymous]

Anonymous wrote:How old is the boss and what is his background (tech, law, etc)? What's the vibe of the office (if you know)?

Oh also what restaurant/how formal is it?

[Anonymous]

Anonymous wrote:How old is the boss and what is his background (tech, law, etc)? What's the vibe of the office (if you know)?

He’s younger than 50, older than 45. The office dress code is jeans. And I’m not sure where we are going yet but I feel like blazers and dress pants would feel too formal. We have a great professional relationship . Just wondering if I could pull off nice dark jeans, but what on top and what shoes.

[Anonymous]

Black pants silk blouse, or unsexy dress with tall boots.

[Anonymous]

I’d wear a dress and boots. Something from j McLaughlin. Can’t go wrong.

[Anonymous]

Omg NO do not wear a suit or slacks! Dark jeans, nice blouse or sweater or tshirt with a blazer. Nice shoes. Wear makeup and do your hair.

- big tech exec who has employees across the country

[Anonymous]

Anonymous wrote:Omg NO do not wear a suit or slacks! Dark jeans, nice blouse or sweater or tshirt with a blazer. Nice shoes. Wear makeup and do your hair.

- big tech exec who has employees across the country

Thank you!!

[Anonymous]

Anonymous wrote:Omg NO do not wear a suit or slacks! Dark jeans, nice blouse or sweater or tshirt with a blazer. Nice shoes. Wear makeup and do your hair.

- big tech exec who has employees across the country

Why not?

[Anonymous]

Anonymous wrote:

Anonymous wrote:How old is the boss and what is his background (tech, law, etc)? What's the vibe of the office (if you know)?

He’s younger than 50, older than 45. The office dress code is jeans. And I’m not sure where we are going yet but I feel like blazers and dress pants would feel too formal. We have a great professional relationship . Just wondering if I could pull off nice dark jeans, but what on top and what shoes.

Yeah I think you'd look too fussy in a blazer and pants, if the office vibe (and your boss's vibe) is more casual. Dark jeans sound good - or a casual but nice dress with ankle boots.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:How old is the boss and what is his background (tech, law, etc)? What's the vibe of the office (if you know)?

He’s younger than 50, older than 45. The office dress code is jeans. And I’m not sure where we are going yet but I feel like blazers and dress pants would feel too formal. We have a great professional relationship . Just wondering if I could pull off nice dark jeans, but what on top and what shoes.

Yeah I think you'd look too fussy in a blazer and pants, if the office vibe (and your boss's vibe) is more casual. Dark jeans sound good - or a casual but nice dress with ankle boots.

I disagree - I think a sweater blazer would be fine. Gives you a casual professional vibe without looking too dressy and can also double as a jacket. And just wear something simple but nice underneath like a blouse or short sleeved cashmere sweater. Slim pants and casual non-sneaker shoes or flats.

[Anonymous]

Blazer with t-shirt or blouse, nice dark jeans, nice flats or booties. Do your hair (and I'm not talking some sort of big styled hair) and maybe mascara.

You show that you care about your appearance, but aren't trying too hard.